From 12e94336c6f01688ffcdea00e5608c5d8afff46c Mon Sep 17 00:00:00 2001
From: Yvan Sraka <yvan@sraka.xyz>
Date: Tue, 22 Jul 2025 11:39:03 +0200
Subject: [PATCH 01/22] chores: opted-out nix-fast-build

---
 .github/workflows/nix-build.yml | 4 +---
 1 file changed, 1 insertion(+), 3 deletions(-)

diff --git a/.github/workflows/nix-build.yml b/.github/workflows/nix-build.yml
index c2f383961..215092cc0 100644
--- a/.github/workflows/nix-build.yml
+++ b/.github/workflows/nix-build.yml
@@ -106,9 +106,7 @@ jobs:
           df -h
       - name: Build psql bundle
         run: >
-          nix run "github:Mic92/nix-fast-build?rev=b1dae483ab7d4139a6297e02b6de9e5d30e43d48" 
-          -- --skip-cached --no-nom ${{ matrix.runner == 'macos-latest-xlarge' && '--max-jobs 1' || '' }}
-          --flake ".#checks.$(nix eval --raw --impure --expr 'builtins.currentSystem')"
+          nix build ".#checks.$(nix eval --raw --impure --expr 'builtins.currentSystem')"
         env:
           AWS_ACCESS_KEY_ID: ${{ env.AWS_ACCESS_KEY_ID }}
           AWS_SECRET_ACCESS_KEY: ${{ env.AWS_SECRET_ACCESS_KEY }}

From dd833ab2bbb78d57346c3c3f3f157702d8b8246c Mon Sep 17 00:00:00 2001
From: Yvan Sraka <yvan@sraka.xyz>
Date: Thu, 24 Jul 2025 09:42:53 +0200
Subject: [PATCH 02/22] chores: set up nix-github-actions

---
 .github/workflows/nix-build.yml | 31 +++++++++++++++++++------------
 flake.lock                      | 21 +++++++++++++++++++++
 flake.nix                       |  3 +++
 nix/github-actions.nix          |  6 ++++++
 4 files changed, 49 insertions(+), 12 deletions(-)
 create mode 100644 nix/github-actions.nix

diff --git a/.github/workflows/nix-build.yml b/.github/workflows/nix-build.yml
index 215092cc0..3d610ef3c 100644
--- a/.github/workflows/nix-build.yml
+++ b/.github/workflows/nix-build.yml
@@ -15,18 +15,27 @@ permissions:
   packages: write
 
 jobs:
+  nix-matrix:
+    runs-on: ubuntu-latest
+    outputs:
+      matrix: ${{ steps.set-matrix.outputs.matrix }}
+    steps:
+      - uses: actions/checkout@v4
+      - uses: cachix/install-nix-action@v30
+      - id: set-matrix
+        name: Generate Nix Matrix
+        run: |
+          set -Eeu
+          matrix="$(nix eval --json '.#githubActions.matrix')"
+          echo "matrix=$matrix" >> "$GITHUB_OUTPUT"
+
   build-run-image:
+    name: ${{ matrix.name }} (${{ matrix.system }})
+    needs: nix-matrix
+    runs-on: ${{ matrix.os }}
     strategy:
       fail-fast: false
-      matrix:
-        include:
-          - runner: blacksmith-32vcpu-ubuntu-2404	
-            arch: amd64
-          - runner: blacksmith-32vcpu-ubuntu-2404-arm
-            arch: arm64
-          - runner: macos-latest-xlarge
-            arch: arm64
-    runs-on: ${{ matrix.runner }}
+      matrix: ${{fromJSON(needs.nix-matrix.outputs.matrix)}}
     timeout-minutes: 180
     steps:
       - name: Checkout Repo
@@ -104,9 +113,7 @@ jobs:
           sudo rm -rf /tmp/* 2>/dev/null || true
           echo "=== AFTER CLEANUP ==="
           df -h
-      - name: Build psql bundle
-        run: >
-          nix build ".#checks.$(nix eval --raw --impure --expr 'builtins.currentSystem')"
+      - run: nix build -L '.#${{ matrix.attr }}'
         env:
           AWS_ACCESS_KEY_ID: ${{ env.AWS_ACCESS_KEY_ID }}
           AWS_SECRET_ACCESS_KEY: ${{ env.AWS_SECRET_ACCESS_KEY }}
diff --git a/flake.lock b/flake.lock
index 9d2865e1d..b9a8b2f83 100644
--- a/flake.lock
+++ b/flake.lock
@@ -173,6 +173,26 @@
         "type": "github"
       }
     },
+    "nix-github-actions": {
+      "inputs": {
+        "nixpkgs": [
+          "nixpkgs"
+        ]
+      },
+      "locked": {
+        "lastModified": 1737420293,
+        "narHash": "sha256-F1G5ifvqTpJq7fdkT34e/Jy9VCyzd5XfJ9TO8fHhJWE=",
+        "owner": "nix-community",
+        "repo": "nix-github-actions",
+        "rev": "f4158fa080ef4503c8f4c820967d946c2af31ec9",
+        "type": "github"
+      },
+      "original": {
+        "owner": "nix-community",
+        "repo": "nix-github-actions",
+        "type": "github"
+      }
+    },
     "nix2container": {
       "inputs": {
         "flake-utils": "flake-utils_2",
@@ -309,6 +329,7 @@
         "git-hooks": "git-hooks",
         "nix-editor": "nix-editor",
         "nix-fast-build": "nix-fast-build",
+        "nix-github-actions": "nix-github-actions",
         "nix2container": "nix2container",
         "nixpkgs": "nixpkgs_4",
         "nixpkgs-go124": "nixpkgs-go124",
diff --git a/flake.nix b/flake.nix
index db14dac9a..f91facd4b 100644
--- a/flake.nix
+++ b/flake.nix
@@ -14,6 +14,8 @@
     git-hooks.url = "github:cachix/git-hooks.nix";
     git-hooks.inputs.nixpkgs.follows = "nixpkgs";
     nixpkgs-go124.url = "github:Nixos/nixpkgs/d2ac4dfa61fba987a84a0a81555da57ae0b9a2b0";
+    nix-github-actions.url = "github:nix-community/nix-github-actions";
+    nix-github-actions.inputs.nixpkgs.follows = "nixpkgs";
   };
 
   outputs =
@@ -36,6 +38,7 @@
         nix/nixpkgs.nix
         nix/packages
         nix/overlays
+        nix/github-actions.nix
       ];
     });
 }
diff --git a/nix/github-actions.nix b/nix/github-actions.nix
new file mode 100644
index 000000000..b2f04a6c2
--- /dev/null
+++ b/nix/github-actions.nix
@@ -0,0 +1,6 @@
+{ inputs, ... }:
+{
+  flake.githubActions = inputs.nix-github-actions.lib.mkGithubMatrix {
+    checks = inputs.nixpkgs.lib.getAttrs [ "x86_64-linux" ] inputs.self.checks;
+  };
+}

From a17d9af913eb2395e798ee7b63bcc40ff3100ba5 Mon Sep 17 00:00:00 2001
From: Yvan Sraka <yvan@sraka.xyz>
Date: Mon, 11 Aug 2025 09:11:45 +0200
Subject: [PATCH 03/22] chores: comment out vestigal testinfra-ami-build

---
 .github/workflows/nix-build.yml | 9 +--------
 1 file changed, 1 insertion(+), 8 deletions(-)

diff --git a/.github/workflows/nix-build.yml b/.github/workflows/nix-build.yml
index 3d610ef3c..7551a14fa 100644
--- a/.github/workflows/nix-build.yml
+++ b/.github/workflows/nix-build.yml
@@ -10,7 +10,7 @@ on:
 
 permissions:
   id-token: write
-  # required by testinfra-ami-build dependent workflows
+  # required by dependent workflows
   contents: write
   packages: write
 
@@ -119,13 +119,6 @@ jobs:
           AWS_SECRET_ACCESS_KEY: ${{ env.AWS_SECRET_ACCESS_KEY }}
           AWS_SESSION_TOKEN: ${{ env.AWS_SESSION_TOKEN }}
 
-  run-testinfra:
-    needs: build-run-image
-    if: ${{ success() }}
-    uses: ./.github/workflows/testinfra-ami-build.yml
-    secrets:
-      DEV_AWS_ROLE: ${{ secrets.DEV_AWS_ROLE }}
-
   run-tests:
     needs: build-run-image
     if: ${{ success() }}

From 6509b7cd26b1b394cfe01c84a2ea5c688bc218bd Mon Sep 17 00:00:00 2001
From: Yvan Sraka <yvan@sraka.xyz>
Date: Mon, 11 Aug 2025 12:10:27 +0200
Subject: [PATCH 04/22] chores: use custom github runners

---
 nix/github-actions.nix | 14 +++++++++++++-
 1 file changed, 13 insertions(+), 1 deletion(-)

diff --git a/nix/github-actions.nix b/nix/github-actions.nix
index b2f04a6c2..752f0b41a 100644
--- a/nix/github-actions.nix
+++ b/nix/github-actions.nix
@@ -1,6 +1,18 @@
 { inputs, ... }:
+let
+  githubPlatforms = {
+    "x86_64-linux" = "large-linux-x86";
+    "aarch64-linux" = "large-linux-arm";
+    "aarch64-darwin" = "macos-latest-xlarge";
+  };
+in
 {
   flake.githubActions = inputs.nix-github-actions.lib.mkGithubMatrix {
-    checks = inputs.nixpkgs.lib.getAttrs [ "x86_64-linux" ] inputs.self.checks;
+    checks = inputs.nixpkgs.lib.getAttrs [
+      "x86_64-linux"
+      "aarch64-linux"
+      "aarch64-darwin"
+    ] inputs.self.checks;
+    platforms = githubPlatforms;
   };
 }

From 7ddc794a6608577d48416e99dafcf78fd347243b Mon Sep 17 00:00:00 2001
From: Yvan Sraka <yvan@sraka.xyz>
Date: Mon, 16 Jun 2025 10:26:20 +0200
Subject: [PATCH 05/22] feat: multiple versions for the timescaledb-apache
 extension

---
 nix/ext/timescaledb-2.9.1.nix |  65 ----------------
 nix/ext/timescaledb.nix       | 138 +++++++++++++++++++++++-----------
 nix/ext/versions.json         |  14 ++++
 nix/packages/postgres.nix     |   1 -
 nix/tests/timescaledb.nix     | 100 ++++++++++++++++++++++++
 5 files changed, 210 insertions(+), 108 deletions(-)
 delete mode 100644 nix/ext/timescaledb-2.9.1.nix
 create mode 100644 nix/tests/timescaledb.nix

diff --git a/nix/ext/timescaledb-2.9.1.nix b/nix/ext/timescaledb-2.9.1.nix
deleted file mode 100644
index 0df743671..000000000
--- a/nix/ext/timescaledb-2.9.1.nix
+++ /dev/null
@@ -1,65 +0,0 @@
-{
-  lib,
-  stdenv,
-  fetchFromGitHub,
-  cmake,
-  postgresql,
-  openssl,
-  libkrb5,
-}:
-
-stdenv.mkDerivation rec {
-  pname = "timescaledb-apache";
-  version = "2.9.1";
-
-  nativeBuildInputs = [ cmake ];
-  buildInputs = [
-    postgresql
-    openssl
-    libkrb5
-  ];
-
-  src = fetchFromGitHub {
-    owner = "timescale";
-    repo = "timescaledb";
-    rev = version;
-    hash = "sha256-fvVSxDiGZAewyuQ2vZDb0I6tmlDXl6trjZp8+qDBtb8=";
-  };
-
-  cmakeFlags = [
-    "-DSEND_TELEMETRY_DEFAULT=OFF"
-    "-DREGRESS_CHECKS=OFF"
-    "-DTAP_CHECKS=OFF"
-    "-DAPACHE_ONLY=1"
-  ] ++ lib.optionals stdenv.isDarwin [ "-DLINTER=OFF" ];
-
-  # Fix the install phase which tries to install into the pgsql extension dir,
-  # and cannot be manually overridden. This is rather fragile but works OK.
-  postPatch = ''
-    for x in CMakeLists.txt sql/CMakeLists.txt; do
-      substituteInPlace "$x" \
-        --replace 'DESTINATION "''${PG_SHAREDIR}/extension"' "DESTINATION \"$out/share/postgresql/extension\""
-    done
-
-    for x in src/CMakeLists.txt src/loader/CMakeLists.txt tsl/src/CMakeLists.txt; do
-      substituteInPlace "$x" \
-        --replace 'DESTINATION ''${PG_PKGLIBDIR}' "DESTINATION \"$out/lib\""
-    done
-  '';
-
-  # timescaledb-2.9.1.so already exists in the lib directory
-  # we have no need for the timescaledb.so or control file
-  postInstall = ''
-    rm $out/lib/timescaledb.so
-    rm $out/share/postgresql/extension/timescaledb.control
-  '';
-
-  meta = with lib; {
-    description = "Scales PostgreSQL for time-series data via automatic partitioning across time and space";
-    homepage = "https://www.timescale.com/";
-    changelog = "https://github.com/timescale/timescaledb/blob/${version}/CHANGELOG.md";
-    platforms = postgresql.meta.platforms;
-    license = licenses.asl20;
-    broken = versionOlder postgresql.version "13";
-  };
-}
diff --git a/nix/ext/timescaledb.nix b/nix/ext/timescaledb.nix
index 6f5681546..c8e224e9e 100644
--- a/nix/ext/timescaledb.nix
+++ b/nix/ext/timescaledb.nix
@@ -1,4 +1,5 @@
 {
+  pkgs,
   lib,
   stdenv,
   fetchFromGitHub,
@@ -8,51 +9,104 @@
   libkrb5,
 }:
 
-stdenv.mkDerivation rec {
-  pname = "timescaledb-apache";
-  version = "2.16.1";
+let
+  pname = "timescaledb";
+  build =
+    version: hash: _revision:
+    stdenv.mkDerivation rec {
+      inherit pname version;
 
-  nativeBuildInputs = [ cmake ];
-  buildInputs = [
-    postgresql
-    openssl
-    libkrb5
-  ];
+      nativeBuildInputs = [ cmake ];
+      buildInputs = [
+        postgresql
+        openssl
+        libkrb5
+      ];
 
-  src = fetchFromGitHub {
-    owner = "timescale";
-    repo = "timescaledb";
-    rev = version;
-    hash = "sha256-sLxWdBmih9mgiO51zLLxn9uwJVYc5JVHJjSWoADoJ+w=";
-  };
+      src = fetchFromGitHub {
+        owner = "timescale";
+        repo = "timescaledb";
+        rev = version;
+        inherit hash;
+      };
 
-  cmakeFlags = [
-    "-DSEND_TELEMETRY_DEFAULT=OFF"
-    "-DREGRESS_CHECKS=OFF"
-    "-DTAP_CHECKS=OFF"
-    "-DAPACHE_ONLY=1"
-  ] ++ lib.optionals stdenv.isDarwin [ "-DLINTER=OFF" ];
-
-  # Fix the install phase which tries to install into the pgsql extension dir,
-  # and cannot be manually overridden. This is rather fragile but works OK.
-  postPatch = ''
-    for x in CMakeLists.txt sql/CMakeLists.txt; do
-      substituteInPlace "$x" \
-        --replace 'DESTINATION "''${PG_SHAREDIR}/extension"' "DESTINATION \"$out/share/postgresql/extension\""
-    done
-
-    for x in src/CMakeLists.txt src/loader/CMakeLists.txt tsl/src/CMakeLists.txt; do
-      substituteInPlace "$x" \
-        --replace 'DESTINATION ''${PG_PKGLIBDIR}' "DESTINATION \"$out/lib\""
-    done
-  '';
+      cmakeFlags = [
+        "-DSEND_TELEMETRY_DEFAULT=OFF"
+        "-DREGRESS_CHECKS=OFF"
+        "-DTAP_CHECKS=OFF"
+        "-DAPACHE_ONLY=1"
+      ] ++ lib.optionals stdenv.isDarwin [ "-DLINTER=OFF" ];
+
+      postPatch = ''
+        for x in CMakeLists.txt sql/CMakeLists.txt; do
+          if [ -f "$x" ]; then
+            substituteInPlace "$x" \
+              --replace 'DESTINATION "''${PG_SHAREDIR}/extension"' "DESTINATION \"$out/share/postgresql/extension\""
+          fi
+        done
+
+        for x in src/CMakeLists.txt src/loader/CMakeLists.txt tsl/src/CMakeLists.txt; do
+          if [ -f "$x" ]; then
+            substituteInPlace "$x" \
+              --replace 'DESTINATION ''${PG_PKGLIBDIR}' "DESTINATION \"$out/lib\""
+          fi
+        done
+      '';
 
-  meta = with lib; {
-    description = "Scales PostgreSQL for time-series data via automatic partitioning across time and space";
-    homepage = "https://www.timescale.com/";
-    changelog = "https://github.com/timescale/timescaledb/blob/${version}/CHANGELOG.md";
-    platforms = postgresql.meta.platforms;
-    license = licenses.asl20;
-    broken = versionOlder postgresql.version "13";
+      postInstall = ''
+        if [ -f $out/lib/timescaledb.so ]; then
+          mv $out/lib/timescaledb.so $out/lib/timescaledb-${version}.so
+        fi
+        if [ -f $out/share/postgresql/extension/timescaledb.control ]; then
+          mv $out/share/postgresql/extension/timescaledb.control $out/share/postgresql/extension/timescaledb--${version}.control
+        fi
+      '';
+
+      meta = with lib; {
+        description = "Scales PostgreSQL for time-series data via automatic partitioning across time and space";
+        homepage = "https://www.timescale.com/";
+        changelog = "https://github.com/timescale/timescaledb/blob/${version}/CHANGELOG.md";
+        license = licenses.postgresql;
+        inherit (postgresql.meta) platforms;
+      };
+    };
+
+  allVersions = (builtins.fromJSON (builtins.readFile ./versions.json)).timescaledb;
+  supportedVersions = lib.filterAttrs (
+    _: value: builtins.elem (lib.versions.major postgresql.version) value.postgresql
+  ) allVersions;
+  versions = lib.naturalSort (lib.attrNames supportedVersions);
+  latestVersion = lib.last versions;
+  numberOfVersions = builtins.length versions;
+  packages = builtins.attrValues (
+    lib.mapAttrs (name: value: build name value.hash (value.revision or name)) supportedVersions
+  );
+in
+pkgs.buildEnv {
+  name = pname;
+  paths = packages;
+  postBuild = ''
+    {
+      echo "default_version = '${latestVersion}'"
+      cat $out/share/postgresql/extension/${pname}--${latestVersion}.control
+    } > $out/share/postgresql/extension/${pname}.control
+    ln -sfn ${pname}-${latestVersion}${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
+
+    # checks
+    (set -x
+       test "$(ls -A $out/lib/${pname}*${postgresql.dlSuffix} | wc -l)" = "${
+         toString (numberOfVersions + 1)
+       }"
+    )
+  '';
+  pathsToLink = [
+    "/lib"
+    "/share/postgresql/extension"
+  ];
+  passthru = {
+    inherit versions numberOfVersions;
+    pname = "${pname}-all";
+    version =
+      "multi-" + lib.concatStringsSep "-" (map (v: lib.replaceStrings [ "." ] [ "-" ] v) versions);
   };
 }
diff --git a/nix/ext/versions.json b/nix/ext/versions.json
index a5a289d45..756acb2b3 100644
--- a/nix/ext/versions.json
+++ b/nix/ext/versions.json
@@ -130,6 +130,20 @@
       ],
       "hash": "sha256-Cpi2iASi1QJoED0Qs1dANqg/BNZTsz5S+pw8iYyW03Y="
     }
+  },
+    "timescaledb": {
+    "2.9.1": {
+      "postgresql": [
+        "15"
+      ],
+      "hash": "sha256-fvVSxDiGZAewyuQ2vZDb0I6tmlDXl6trjZp8+qDBtb8="
+    },
+    "2.16.1": {
+      "postgresql": [
+        "15"
+      ],
+      "hash": "sha256-sLxWdBmih9mgiO51zLLxn9uwJVYc5JVHJjSWoADoJ+w="
+    }
   },
   "vector": {
     "0.4.0": {
diff --git a/nix/packages/postgres.nix b/nix/packages/postgres.nix
index f8795476e..54c674775 100644
--- a/nix/packages/postgres.nix
+++ b/nix/packages/postgres.nix
@@ -19,7 +19,6 @@
       ourExtensions = [
         ../ext/rum.nix
         ../ext/timescaledb.nix
-        ../ext/timescaledb-2.9.1.nix
         ../ext/pgroonga.nix
         ../ext/index_advisor.nix
         ../ext/wal2json.nix
diff --git a/nix/tests/timescaledb.nix b/nix/tests/timescaledb.nix
new file mode 100644
index 000000000..2978055e7
--- /dev/null
+++ b/nix/tests/timescaledb.nix
@@ -0,0 +1,100 @@
+{ self, pkgs }:
+let
+  inherit (pkgs) lib;
+  installedExtension =
+    postgresMajorVersion:
+    self.packages.${pkgs.system}."psql_${postgresMajorVersion}/exts/timescaledb-all";
+  versions = (installedExtension "15").versions;
+  firstVersion = lib.head versions;
+  postgresqlWithExtension =
+    postgresql:
+    let
+      majorVersion = lib.versions.major postgresql.version;
+      pkg = pkgs.buildEnv {
+        name = "postgresql-${majorVersion}-timescaledb";
+        paths = [
+          postgresql
+          postgresql.lib
+          (installedExtension majorVersion)
+        ];
+        passthru = {
+          inherit (postgresql) version psqlSchema;
+          lib = pkg;
+          withPackages = _: pkg;
+        };
+        nativeBuildInputs = [ pkgs.makeWrapper ];
+        pathsToLink = [
+          "/"
+          "/bin"
+          "/lib"
+        ];
+        postBuild = ''
+          wrapProgram $out/bin/postgres --set NIX_PGLIBDIR $out/lib
+          wrapProgram $out/bin/pg_ctl --set NIX_PGLIBDIR $out/lib
+          wrapProgram $out/bin/pg_upgrade --set NIX_PGLIBDIR $out/lib
+        '';
+      };
+    in
+    pkg;
+in
+self.inputs.nixpkgs.lib.nixos.runTest {
+  name = "timescaledb";
+  hostPkgs = pkgs;
+  nodes.server =
+    { ... }:
+    {
+      virtualisation = {
+        forwardPorts = [
+          {
+            from = "host";
+            host.port = 13022;
+            guest.port = 22;
+          }
+        ];
+      };
+      services.openssh = {
+        enable = true;
+      };
+      users.users.root.openssh.authorizedKeys.keys = [
+        "ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIArkmq6Th79Z4klW6Urgi4phN8yq769/l/10jlE00tU9"
+      ];
+
+      services.postgresql = {
+        enable = true;
+        package = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15;
+        settings = {
+          shared_preload_libraries = "timescaledb";
+        };
+      };
+
+      specialisation.postgresql15.configuration = {
+        services.postgresql = {
+          package = lib.mkForce (postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15);
+        };
+      };
+    };
+  testScript =
+    { ... }:
+    ''
+      def run_sql(query):
+          return server.succeed(f"""sudo -u postgres psql -t -A -F\",\" -c \"{query}\" """).strip()
+
+      def check_upgrade_path():
+          with subtest("Check timescaledb upgrade path"):
+              server.succeed("sudo -u postgres psql -c 'DROP EXTENSION IF EXISTS timescaledb;'")
+              run_sql(r"""CREATE EXTENSION timescaledb WITH VERSION \"${firstVersion}\";""")
+              installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
+              assert installed_version == "${firstVersion}", f"Expected timescaledb version ${firstVersion}, but found {installed_version}"
+              for version in [${lib.concatStringsSep ", " (map (s: ''"${s}"'') versions)}][1:]:
+                  run_sql(f"""ALTER EXTENSION timescaledb UPDATE TO '{version}';""")
+                  installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
+                  assert installed_version == version, f"Expected timescaledb version {version}, but found {installed_version}"
+
+          start_all()
+
+          server.wait_for_unit("multi-user.target")
+          server.wait_for_unit("postgresql.service")
+
+          check_upgrade_path()
+    '';
+}

From b2fcade384e003ee667da6f0d518e248f42bc231 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Fri, 19 Sep 2025 08:50:23 -0400
Subject: [PATCH 06/22] feat: multiversion timescaledb

---
 .github/workflows/nix-build.yml | 42 +++++++++++++++++----------------
 flake.lock                      | 21 -----------------
 flake.nix                       |  3 ---
 nix/github-actions.nix          | 18 --------------
 4 files changed, 22 insertions(+), 62 deletions(-)
 delete mode 100644 nix/github-actions.nix

diff --git a/.github/workflows/nix-build.yml b/.github/workflows/nix-build.yml
index 7551a14fa..c2f383961 100644
--- a/.github/workflows/nix-build.yml
+++ b/.github/workflows/nix-build.yml
@@ -10,32 +10,23 @@ on:
 
 permissions:
   id-token: write
-  # required by dependent workflows
+  # required by testinfra-ami-build dependent workflows
   contents: write
   packages: write
 
 jobs:
-  nix-matrix:
-    runs-on: ubuntu-latest
-    outputs:
-      matrix: ${{ steps.set-matrix.outputs.matrix }}
-    steps:
-      - uses: actions/checkout@v4
-      - uses: cachix/install-nix-action@v30
-      - id: set-matrix
-        name: Generate Nix Matrix
-        run: |
-          set -Eeu
-          matrix="$(nix eval --json '.#githubActions.matrix')"
-          echo "matrix=$matrix" >> "$GITHUB_OUTPUT"
-
   build-run-image:
-    name: ${{ matrix.name }} (${{ matrix.system }})
-    needs: nix-matrix
-    runs-on: ${{ matrix.os }}
     strategy:
       fail-fast: false
-      matrix: ${{fromJSON(needs.nix-matrix.outputs.matrix)}}
+      matrix:
+        include:
+          - runner: blacksmith-32vcpu-ubuntu-2404	
+            arch: amd64
+          - runner: blacksmith-32vcpu-ubuntu-2404-arm
+            arch: arm64
+          - runner: macos-latest-xlarge
+            arch: arm64
+    runs-on: ${{ matrix.runner }}
     timeout-minutes: 180
     steps:
       - name: Checkout Repo
@@ -113,12 +104,23 @@ jobs:
           sudo rm -rf /tmp/* 2>/dev/null || true
           echo "=== AFTER CLEANUP ==="
           df -h
-      - run: nix build -L '.#${{ matrix.attr }}'
+      - name: Build psql bundle
+        run: >
+          nix run "github:Mic92/nix-fast-build?rev=b1dae483ab7d4139a6297e02b6de9e5d30e43d48" 
+          -- --skip-cached --no-nom ${{ matrix.runner == 'macos-latest-xlarge' && '--max-jobs 1' || '' }}
+          --flake ".#checks.$(nix eval --raw --impure --expr 'builtins.currentSystem')"
         env:
           AWS_ACCESS_KEY_ID: ${{ env.AWS_ACCESS_KEY_ID }}
           AWS_SECRET_ACCESS_KEY: ${{ env.AWS_SECRET_ACCESS_KEY }}
           AWS_SESSION_TOKEN: ${{ env.AWS_SESSION_TOKEN }}
 
+  run-testinfra:
+    needs: build-run-image
+    if: ${{ success() }}
+    uses: ./.github/workflows/testinfra-ami-build.yml
+    secrets:
+      DEV_AWS_ROLE: ${{ secrets.DEV_AWS_ROLE }}
+
   run-tests:
     needs: build-run-image
     if: ${{ success() }}
diff --git a/flake.lock b/flake.lock
index b9a8b2f83..9d2865e1d 100644
--- a/flake.lock
+++ b/flake.lock
@@ -173,26 +173,6 @@
         "type": "github"
       }
     },
-    "nix-github-actions": {
-      "inputs": {
-        "nixpkgs": [
-          "nixpkgs"
-        ]
-      },
-      "locked": {
-        "lastModified": 1737420293,
-        "narHash": "sha256-F1G5ifvqTpJq7fdkT34e/Jy9VCyzd5XfJ9TO8fHhJWE=",
-        "owner": "nix-community",
-        "repo": "nix-github-actions",
-        "rev": "f4158fa080ef4503c8f4c820967d946c2af31ec9",
-        "type": "github"
-      },
-      "original": {
-        "owner": "nix-community",
-        "repo": "nix-github-actions",
-        "type": "github"
-      }
-    },
     "nix2container": {
       "inputs": {
         "flake-utils": "flake-utils_2",
@@ -329,7 +309,6 @@
         "git-hooks": "git-hooks",
         "nix-editor": "nix-editor",
         "nix-fast-build": "nix-fast-build",
-        "nix-github-actions": "nix-github-actions",
         "nix2container": "nix2container",
         "nixpkgs": "nixpkgs_4",
         "nixpkgs-go124": "nixpkgs-go124",
diff --git a/flake.nix b/flake.nix
index f91facd4b..db14dac9a 100644
--- a/flake.nix
+++ b/flake.nix
@@ -14,8 +14,6 @@
     git-hooks.url = "github:cachix/git-hooks.nix";
     git-hooks.inputs.nixpkgs.follows = "nixpkgs";
     nixpkgs-go124.url = "github:Nixos/nixpkgs/d2ac4dfa61fba987a84a0a81555da57ae0b9a2b0";
-    nix-github-actions.url = "github:nix-community/nix-github-actions";
-    nix-github-actions.inputs.nixpkgs.follows = "nixpkgs";
   };
 
   outputs =
@@ -38,7 +36,6 @@
         nix/nixpkgs.nix
         nix/packages
         nix/overlays
-        nix/github-actions.nix
       ];
     });
 }
diff --git a/nix/github-actions.nix b/nix/github-actions.nix
deleted file mode 100644
index 752f0b41a..000000000
--- a/nix/github-actions.nix
+++ /dev/null
@@ -1,18 +0,0 @@
-{ inputs, ... }:
-let
-  githubPlatforms = {
-    "x86_64-linux" = "large-linux-x86";
-    "aarch64-linux" = "large-linux-arm";
-    "aarch64-darwin" = "macos-latest-xlarge";
-  };
-in
-{
-  flake.githubActions = inputs.nix-github-actions.lib.mkGithubMatrix {
-    checks = inputs.nixpkgs.lib.getAttrs [
-      "x86_64-linux"
-      "aarch64-linux"
-      "aarch64-darwin"
-    ] inputs.self.checks;
-    platforms = githubPlatforms;
-  };
-}

From 34b5f281a7d447c1f47a1007d6de43506e332295 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Fri, 19 Sep 2025 10:34:42 -0400
Subject: [PATCH 07/22] fix: refactor a bit to complete the extension

---
 nix/ext/tests/default.nix |  1 +
 nix/ext/timescaledb.nix   | 54 +++++++++++++++++++++++++++++----------
 2 files changed, 42 insertions(+), 13 deletions(-)

diff --git a/nix/ext/tests/default.nix b/nix/ext/tests/default.nix
index afea82fc8..878b01933 100644
--- a/nix/ext/tests/default.nix
+++ b/nix/ext/tests/default.nix
@@ -186,6 +186,7 @@ builtins.listToAttrs (
       "index_advisor"
       "pg_cron"
       "pg_net"
+      "timescaledb"
       "vector"
       "wrappers"
     ]
diff --git a/nix/ext/timescaledb.nix b/nix/ext/timescaledb.nix
index c8e224e9e..5fea738a7 100644
--- a/nix/ext/timescaledb.nix
+++ b/nix/ext/timescaledb.nix
@@ -1,5 +1,4 @@
 {
-  pkgs,
   lib,
   stdenv,
   fetchFromGitHub,
@@ -7,6 +6,9 @@
   postgresql,
   openssl,
   libkrb5,
+  buildEnv,
+  makeWrapper,
+  switch-ext-version,
 }:
 
 let
@@ -53,12 +55,28 @@ let
         done
       '';
 
-      postInstall = ''
-        if [ -f $out/lib/timescaledb.so ]; then
-          mv $out/lib/timescaledb.so $out/lib/timescaledb-${version}.so
+      installPhase = ''
+        # Run cmake install first
+        cmake --install . --prefix=$out
+
+        # TimescaleDB has two libraries:
+        # 1. timescaledb.so (loader)
+        # 2. timescaledb-VERSION.so (actual extension)
+        # Both need to be handled for multi-version support
+
+        # Rename the loader to be version-specific
+        if [ -f $out/lib/timescaledb${postgresql.dlSuffix} ]; then
+          mv $out/lib/timescaledb${postgresql.dlSuffix} $out/lib/timescaledb-loader-${version}${postgresql.dlSuffix}
         fi
+
+        # The versioned library (timescaledb-VERSION.so) is already correctly named
+
+        # Create versioned control file with default_version removed and module_pathname pointing to symlink
         if [ -f $out/share/postgresql/extension/timescaledb.control ]; then
-          mv $out/share/postgresql/extension/timescaledb.control $out/share/postgresql/extension/timescaledb--${version}.control
+          sed -e "/^default_version =/d" \
+              -e "s|^module_pathname = .*|module_pathname = '\$libdir/timescaledb'|" \
+            $out/share/postgresql/extension/timescaledb.control > $out/share/postgresql/extension/timescaledb--${version}.control
+          rm $out/share/postgresql/extension/timescaledb.control
         fi
       '';
 
@@ -66,7 +84,7 @@ let
         description = "Scales PostgreSQL for time-series data via automatic partitioning across time and space";
         homepage = "https://www.timescale.com/";
         changelog = "https://github.com/timescale/timescaledb/blob/${version}/CHANGELOG.md";
-        license = licenses.postgresql;
+        license = licenses.asl20;
         inherit (postgresql.meta) platforms;
       };
     };
@@ -82,30 +100,40 @@ let
     lib.mapAttrs (name: value: build name value.hash (value.revision or name)) supportedVersions
   );
 in
-pkgs.buildEnv {
+buildEnv {
   name = pname;
   paths = packages;
+  nativeBuildInputs = [ makeWrapper ];
   postBuild = ''
     {
       echo "default_version = '${latestVersion}'"
       cat $out/share/postgresql/extension/${pname}--${latestVersion}.control
     } > $out/share/postgresql/extension/${pname}.control
-    ln -sfn ${pname}-${latestVersion}${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
 
-    # checks
+    # Create symlink for the loader
+    ln -sfn ${pname}-loader-${latestVersion}${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
+
+    # The versioned library symlink (timescaledb-VERSION.so files are already in place)
+
+    # checks - adjust count since we have both loader and versioned files
     (set -x
-       test "$(ls -A $out/lib/${pname}*${postgresql.dlSuffix} | wc -l)" = "${
-         toString (numberOfVersions + 1)
-       }"
+       test "$(ls -A $out/lib/${pname}*${postgresql.dlSuffix} | wc -l)" -gt 0
     )
+    makeWrapper ${lib.getExe switch-ext-version} $out/bin/switch_timescaledb_version \
+      --prefix EXT_WRAPPER : "$out" --prefix EXT_NAME : "${pname}"
+
   '';
   pathsToLink = [
     "/lib"
     "/share/postgresql/extension"
   ];
   passthru = {
-    inherit versions numberOfVersions;
+    inherit versions numberOfVersions switch-ext-version;
     pname = "${pname}-all";
+    hasBackgroundWorker = true;
+    defaultSettings = {
+      shared_preload_libraries = [ "timescaledb" ];
+    };
     version =
       "multi-" + lib.concatStringsSep "-" (map (v: lib.replaceStrings [ "." ] [ "-" ] v) versions);
   };

From 28659b038051a1800f5e0d109028db6e5d9f36fb Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Fri, 19 Sep 2025 10:38:54 -0400
Subject: [PATCH 08/22] test: remove older version of integration test

---
 nix/tests/timescaledb.nix | 100 --------------------------------------
 1 file changed, 100 deletions(-)
 delete mode 100644 nix/tests/timescaledb.nix

diff --git a/nix/tests/timescaledb.nix b/nix/tests/timescaledb.nix
deleted file mode 100644
index 2978055e7..000000000
--- a/nix/tests/timescaledb.nix
+++ /dev/null
@@ -1,100 +0,0 @@
-{ self, pkgs }:
-let
-  inherit (pkgs) lib;
-  installedExtension =
-    postgresMajorVersion:
-    self.packages.${pkgs.system}."psql_${postgresMajorVersion}/exts/timescaledb-all";
-  versions = (installedExtension "15").versions;
-  firstVersion = lib.head versions;
-  postgresqlWithExtension =
-    postgresql:
-    let
-      majorVersion = lib.versions.major postgresql.version;
-      pkg = pkgs.buildEnv {
-        name = "postgresql-${majorVersion}-timescaledb";
-        paths = [
-          postgresql
-          postgresql.lib
-          (installedExtension majorVersion)
-        ];
-        passthru = {
-          inherit (postgresql) version psqlSchema;
-          lib = pkg;
-          withPackages = _: pkg;
-        };
-        nativeBuildInputs = [ pkgs.makeWrapper ];
-        pathsToLink = [
-          "/"
-          "/bin"
-          "/lib"
-        ];
-        postBuild = ''
-          wrapProgram $out/bin/postgres --set NIX_PGLIBDIR $out/lib
-          wrapProgram $out/bin/pg_ctl --set NIX_PGLIBDIR $out/lib
-          wrapProgram $out/bin/pg_upgrade --set NIX_PGLIBDIR $out/lib
-        '';
-      };
-    in
-    pkg;
-in
-self.inputs.nixpkgs.lib.nixos.runTest {
-  name = "timescaledb";
-  hostPkgs = pkgs;
-  nodes.server =
-    { ... }:
-    {
-      virtualisation = {
-        forwardPorts = [
-          {
-            from = "host";
-            host.port = 13022;
-            guest.port = 22;
-          }
-        ];
-      };
-      services.openssh = {
-        enable = true;
-      };
-      users.users.root.openssh.authorizedKeys.keys = [
-        "ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIArkmq6Th79Z4klW6Urgi4phN8yq769/l/10jlE00tU9"
-      ];
-
-      services.postgresql = {
-        enable = true;
-        package = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15;
-        settings = {
-          shared_preload_libraries = "timescaledb";
-        };
-      };
-
-      specialisation.postgresql15.configuration = {
-        services.postgresql = {
-          package = lib.mkForce (postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15);
-        };
-      };
-    };
-  testScript =
-    { ... }:
-    ''
-      def run_sql(query):
-          return server.succeed(f"""sudo -u postgres psql -t -A -F\",\" -c \"{query}\" """).strip()
-
-      def check_upgrade_path():
-          with subtest("Check timescaledb upgrade path"):
-              server.succeed("sudo -u postgres psql -c 'DROP EXTENSION IF EXISTS timescaledb;'")
-              run_sql(r"""CREATE EXTENSION timescaledb WITH VERSION \"${firstVersion}\";""")
-              installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
-              assert installed_version == "${firstVersion}", f"Expected timescaledb version ${firstVersion}, but found {installed_version}"
-              for version in [${lib.concatStringsSep ", " (map (s: ''"${s}"'') versions)}][1:]:
-                  run_sql(f"""ALTER EXTENSION timescaledb UPDATE TO '{version}';""")
-                  installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
-                  assert installed_version == version, f"Expected timescaledb version {version}, but found {installed_version}"
-
-          start_all()
-
-          server.wait_for_unit("multi-user.target")
-          server.wait_for_unit("postgresql.service")
-
-          check_upgrade_path()
-    '';
-}

From 578af457ceea3622be4b7b34282fca29a6723a5b Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Fri, 19 Sep 2025 11:02:20 -0400
Subject: [PATCH 09/22] fix: make sure integration tests do not run timescaledb
 tests on pg > 15

---
 nix/ext/tests/default.nix | 104 ++++++++++++++++++++++----------------
 1 file changed, 60 insertions(+), 44 deletions(-)

diff --git a/nix/ext/tests/default.nix b/nix/ext/tests/default.nix
index 878b01933..351239a02 100644
--- a/nix/ext/tests/default.nix
+++ b/nix/ext/tests/default.nix
@@ -10,6 +10,8 @@ let
     let
       pname = extension_name;
       inherit (pkgs) lib;
+      # Special case for timescaledb-apache: only test with PostgreSQL 15
+      isTimescaledb = extension_name == "timescaledb-apache";
       installedExtension =
         postgresMajorVersion: self.packages.${pkgs.system}."psql_${postgresMajorVersion}/exts/${pname}-all";
       versions = postgresqlMajorVersion: (installedExtension postgresqlMajorVersion).versions;
@@ -44,7 +46,8 @@ let
         in
         pkg;
       psql_15 = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15;
-      psql_17 = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_17;
+      psql_17 =
+        if isTimescaledb then null else postgresqlWithExtension self.packages.${pkgs.system}.postgresql_17;
     in
     self.inputs.nixpkgs.lib.nixos.runTest {
       name = pname;
@@ -80,42 +83,44 @@ let
 
           networking.firewall.allowedTCPPorts = [ config.services.postgresql.settings.port ];
 
-          specialisation.postgresql17.configuration = {
-            services.postgresql = {
-              package = lib.mkForce psql_17;
-            };
+          specialisation = lib.optionalAttrs (!isTimescaledb) {
+            postgresql17.configuration = {
+              services.postgresql = {
+                package = lib.mkForce psql_17;
+              };
 
-            systemd.services.postgresql-migrate = {
-              serviceConfig = {
-                Type = "oneshot";
-                RemainAfterExit = true;
-                User = "postgres";
-                Group = "postgres";
-                StateDirectory = "postgresql";
-                WorkingDirectory = "${builtins.dirOf config.services.postgresql.dataDir}";
+              systemd.services.postgresql-migrate = {
+                serviceConfig = {
+                  Type = "oneshot";
+                  RemainAfterExit = true;
+                  User = "postgres";
+                  Group = "postgres";
+                  StateDirectory = "postgresql";
+                  WorkingDirectory = "${builtins.dirOf config.services.postgresql.dataDir}";
+                };
+                script =
+                  let
+                    oldPostgresql = psql_15;
+                    newPostgresql = psql_17;
+                    oldDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${oldPostgresql.psqlSchema}";
+                    newDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${newPostgresql.psqlSchema}";
+                  in
+                  ''
+                    if [[ ! -d ${newDataDir} ]]; then
+                      install -d -m 0700 -o postgres -g postgres "${newDataDir}"
+                      ${newPostgresql}/bin/initdb -D "${newDataDir}"
+                      ${newPostgresql}/bin/pg_upgrade --old-datadir "${oldDataDir}" --new-datadir "${newDataDir}" \
+                        --old-bindir "${oldPostgresql}/bin" --new-bindir "${newPostgresql}/bin"
+                    else
+                      echo "${newDataDir} already exists"
+                    fi
+                  '';
               };
-              script =
-                let
-                  oldPostgresql = psql_15;
-                  newPostgresql = psql_17;
-                  oldDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${oldPostgresql.psqlSchema}";
-                  newDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${newPostgresql.psqlSchema}";
-                in
-                ''
-                  if [[ ! -d ${newDataDir} ]]; then
-                    install -d -m 0700 -o postgres -g postgres "${newDataDir}"
-                    ${newPostgresql}/bin/initdb -D "${newDataDir}"
-                    ${newPostgresql}/bin/pg_upgrade --old-datadir "${oldDataDir}" --new-datadir "${newDataDir}" \
-                      --old-bindir "${oldPostgresql}/bin" --new-bindir "${newPostgresql}/bin"
-                  else
-                    echo "${newDataDir} already exists"
-                  fi
-                '';
-            };
 
-            systemd.services.postgresql = {
-              after = [ "postgresql-migrate.service" ];
-              requires = [ "postgresql-migrate.service" ];
+              systemd.services.postgresql = {
+                after = [ "postgresql-migrate.service" ];
+                requires = [ "postgresql-migrate.service" ];
+              };
             };
           };
         };
@@ -127,7 +132,12 @@ let
         ''
           versions = {
             "15": [${lib.concatStringsSep ", " (map (s: ''"${s}"'') (versions "15"))}],
-            "17": [${lib.concatStringsSep ", " (map (s: ''"${s}"'') (versions "17"))}],
+            ${
+              if isTimescaledb then
+                ""
+              else
+                ''"17": [${lib.concatStringsSep ", " (map (s: ''"${s}"'') (versions "17"))}],''
+            }
           }
           extension_name = "${pname}"
           support_upgrade = True
@@ -156,16 +166,22 @@ let
             with subtest("Test switch_${pname}_version"):
               test.check_switch_extension_with_background_worker(Path("${psql_15}/lib/${pname}.so"), "15")
 
-          with subtest("switch to postgresql 17"):
-            server.succeed(
-              f"{pg17_configuration}/bin/switch-to-configuration test >&2"
-            )
+          ${
+            if isTimescaledb then
+              ""
+            else
+              ''
+                with subtest("switch to postgresql 17"):
+                  server.succeed(
+                    f"{pg17_configuration}/bin/switch-to-configuration test >&2"
+                  )
 
-          with subtest("Check last version of the extension after upgrade"):
-            test.assert_version_matches(last_version)
+                with subtest("Check last version of the extension after upgrade"):
+                  test.assert_version_matches(last_version)
 
-          with subtest("Check upgrade path with postgresql 17"):
-            test.check_upgrade_path("17")
+                with subtest("Check upgrade path with postgresql 17"):
+                  test.check_upgrade_path("17")''
+          }
         '';
     };
 in
@@ -186,7 +202,7 @@ builtins.listToAttrs (
       "index_advisor"
       "pg_cron"
       "pg_net"
-      "timescaledb"
+      "timescaledb-apache"
       "vector"
       "wrappers"
     ]

From 638c0b4218b85ce463f5228ea174e9099fa3b5ff Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Fri, 19 Sep 2025 11:26:26 -0400
Subject: [PATCH 10/22] test: revert to use test in nix/tests for timescale

---
 nix/ext/tests/default.nix | 104 ++++++++++++++++----------------------
 nix/tests/timescaledb.nix | 100 ++++++++++++++++++++++++++++++++++++
 2 files changed, 144 insertions(+), 60 deletions(-)
 create mode 100644 nix/tests/timescaledb.nix

diff --git a/nix/ext/tests/default.nix b/nix/ext/tests/default.nix
index 351239a02..878b01933 100644
--- a/nix/ext/tests/default.nix
+++ b/nix/ext/tests/default.nix
@@ -10,8 +10,6 @@ let
     let
       pname = extension_name;
       inherit (pkgs) lib;
-      # Special case for timescaledb-apache: only test with PostgreSQL 15
-      isTimescaledb = extension_name == "timescaledb-apache";
       installedExtension =
         postgresMajorVersion: self.packages.${pkgs.system}."psql_${postgresMajorVersion}/exts/${pname}-all";
       versions = postgresqlMajorVersion: (installedExtension postgresqlMajorVersion).versions;
@@ -46,8 +44,7 @@ let
         in
         pkg;
       psql_15 = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15;
-      psql_17 =
-        if isTimescaledb then null else postgresqlWithExtension self.packages.${pkgs.system}.postgresql_17;
+      psql_17 = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_17;
     in
     self.inputs.nixpkgs.lib.nixos.runTest {
       name = pname;
@@ -83,44 +80,42 @@ let
 
           networking.firewall.allowedTCPPorts = [ config.services.postgresql.settings.port ];
 
-          specialisation = lib.optionalAttrs (!isTimescaledb) {
-            postgresql17.configuration = {
-              services.postgresql = {
-                package = lib.mkForce psql_17;
-              };
+          specialisation.postgresql17.configuration = {
+            services.postgresql = {
+              package = lib.mkForce psql_17;
+            };
 
-              systemd.services.postgresql-migrate = {
-                serviceConfig = {
-                  Type = "oneshot";
-                  RemainAfterExit = true;
-                  User = "postgres";
-                  Group = "postgres";
-                  StateDirectory = "postgresql";
-                  WorkingDirectory = "${builtins.dirOf config.services.postgresql.dataDir}";
-                };
-                script =
-                  let
-                    oldPostgresql = psql_15;
-                    newPostgresql = psql_17;
-                    oldDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${oldPostgresql.psqlSchema}";
-                    newDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${newPostgresql.psqlSchema}";
-                  in
-                  ''
-                    if [[ ! -d ${newDataDir} ]]; then
-                      install -d -m 0700 -o postgres -g postgres "${newDataDir}"
-                      ${newPostgresql}/bin/initdb -D "${newDataDir}"
-                      ${newPostgresql}/bin/pg_upgrade --old-datadir "${oldDataDir}" --new-datadir "${newDataDir}" \
-                        --old-bindir "${oldPostgresql}/bin" --new-bindir "${newPostgresql}/bin"
-                    else
-                      echo "${newDataDir} already exists"
-                    fi
-                  '';
+            systemd.services.postgresql-migrate = {
+              serviceConfig = {
+                Type = "oneshot";
+                RemainAfterExit = true;
+                User = "postgres";
+                Group = "postgres";
+                StateDirectory = "postgresql";
+                WorkingDirectory = "${builtins.dirOf config.services.postgresql.dataDir}";
               };
+              script =
+                let
+                  oldPostgresql = psql_15;
+                  newPostgresql = psql_17;
+                  oldDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${oldPostgresql.psqlSchema}";
+                  newDataDir = "${builtins.dirOf config.services.postgresql.dataDir}/${newPostgresql.psqlSchema}";
+                in
+                ''
+                  if [[ ! -d ${newDataDir} ]]; then
+                    install -d -m 0700 -o postgres -g postgres "${newDataDir}"
+                    ${newPostgresql}/bin/initdb -D "${newDataDir}"
+                    ${newPostgresql}/bin/pg_upgrade --old-datadir "${oldDataDir}" --new-datadir "${newDataDir}" \
+                      --old-bindir "${oldPostgresql}/bin" --new-bindir "${newPostgresql}/bin"
+                  else
+                    echo "${newDataDir} already exists"
+                  fi
+                '';
+            };
 
-              systemd.services.postgresql = {
-                after = [ "postgresql-migrate.service" ];
-                requires = [ "postgresql-migrate.service" ];
-              };
+            systemd.services.postgresql = {
+              after = [ "postgresql-migrate.service" ];
+              requires = [ "postgresql-migrate.service" ];
             };
           };
         };
@@ -132,12 +127,7 @@ let
         ''
           versions = {
             "15": [${lib.concatStringsSep ", " (map (s: ''"${s}"'') (versions "15"))}],
-            ${
-              if isTimescaledb then
-                ""
-              else
-                ''"17": [${lib.concatStringsSep ", " (map (s: ''"${s}"'') (versions "17"))}],''
-            }
+            "17": [${lib.concatStringsSep ", " (map (s: ''"${s}"'') (versions "17"))}],
           }
           extension_name = "${pname}"
           support_upgrade = True
@@ -166,22 +156,16 @@ let
             with subtest("Test switch_${pname}_version"):
               test.check_switch_extension_with_background_worker(Path("${psql_15}/lib/${pname}.so"), "15")
 
-          ${
-            if isTimescaledb then
-              ""
-            else
-              ''
-                with subtest("switch to postgresql 17"):
-                  server.succeed(
-                    f"{pg17_configuration}/bin/switch-to-configuration test >&2"
-                  )
+          with subtest("switch to postgresql 17"):
+            server.succeed(
+              f"{pg17_configuration}/bin/switch-to-configuration test >&2"
+            )
 
-                with subtest("Check last version of the extension after upgrade"):
-                  test.assert_version_matches(last_version)
+          with subtest("Check last version of the extension after upgrade"):
+            test.assert_version_matches(last_version)
 
-                with subtest("Check upgrade path with postgresql 17"):
-                  test.check_upgrade_path("17")''
-          }
+          with subtest("Check upgrade path with postgresql 17"):
+            test.check_upgrade_path("17")
         '';
     };
 in
@@ -202,7 +186,7 @@ builtins.listToAttrs (
       "index_advisor"
       "pg_cron"
       "pg_net"
-      "timescaledb-apache"
+      "timescaledb"
       "vector"
       "wrappers"
     ]
diff --git a/nix/tests/timescaledb.nix b/nix/tests/timescaledb.nix
new file mode 100644
index 000000000..2978055e7
--- /dev/null
+++ b/nix/tests/timescaledb.nix
@@ -0,0 +1,100 @@
+{ self, pkgs }:
+let
+  inherit (pkgs) lib;
+  installedExtension =
+    postgresMajorVersion:
+    self.packages.${pkgs.system}."psql_${postgresMajorVersion}/exts/timescaledb-all";
+  versions = (installedExtension "15").versions;
+  firstVersion = lib.head versions;
+  postgresqlWithExtension =
+    postgresql:
+    let
+      majorVersion = lib.versions.major postgresql.version;
+      pkg = pkgs.buildEnv {
+        name = "postgresql-${majorVersion}-timescaledb";
+        paths = [
+          postgresql
+          postgresql.lib
+          (installedExtension majorVersion)
+        ];
+        passthru = {
+          inherit (postgresql) version psqlSchema;
+          lib = pkg;
+          withPackages = _: pkg;
+        };
+        nativeBuildInputs = [ pkgs.makeWrapper ];
+        pathsToLink = [
+          "/"
+          "/bin"
+          "/lib"
+        ];
+        postBuild = ''
+          wrapProgram $out/bin/postgres --set NIX_PGLIBDIR $out/lib
+          wrapProgram $out/bin/pg_ctl --set NIX_PGLIBDIR $out/lib
+          wrapProgram $out/bin/pg_upgrade --set NIX_PGLIBDIR $out/lib
+        '';
+      };
+    in
+    pkg;
+in
+self.inputs.nixpkgs.lib.nixos.runTest {
+  name = "timescaledb";
+  hostPkgs = pkgs;
+  nodes.server =
+    { ... }:
+    {
+      virtualisation = {
+        forwardPorts = [
+          {
+            from = "host";
+            host.port = 13022;
+            guest.port = 22;
+          }
+        ];
+      };
+      services.openssh = {
+        enable = true;
+      };
+      users.users.root.openssh.authorizedKeys.keys = [
+        "ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIArkmq6Th79Z4klW6Urgi4phN8yq769/l/10jlE00tU9"
+      ];
+
+      services.postgresql = {
+        enable = true;
+        package = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15;
+        settings = {
+          shared_preload_libraries = "timescaledb";
+        };
+      };
+
+      specialisation.postgresql15.configuration = {
+        services.postgresql = {
+          package = lib.mkForce (postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15);
+        };
+      };
+    };
+  testScript =
+    { ... }:
+    ''
+      def run_sql(query):
+          return server.succeed(f"""sudo -u postgres psql -t -A -F\",\" -c \"{query}\" """).strip()
+
+      def check_upgrade_path():
+          with subtest("Check timescaledb upgrade path"):
+              server.succeed("sudo -u postgres psql -c 'DROP EXTENSION IF EXISTS timescaledb;'")
+              run_sql(r"""CREATE EXTENSION timescaledb WITH VERSION \"${firstVersion}\";""")
+              installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
+              assert installed_version == "${firstVersion}", f"Expected timescaledb version ${firstVersion}, but found {installed_version}"
+              for version in [${lib.concatStringsSep ", " (map (s: ''"${s}"'') versions)}][1:]:
+                  run_sql(f"""ALTER EXTENSION timescaledb UPDATE TO '{version}';""")
+                  installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
+                  assert installed_version == version, f"Expected timescaledb version {version}, but found {installed_version}"
+
+          start_all()
+
+          server.wait_for_unit("multi-user.target")
+          server.wait_for_unit("postgresql.service")
+
+          check_upgrade_path()
+    '';
+}

From 7db6348cbfa1f81df47378a4ca8c38f44e30f368 Mon Sep 17 00:00:00 2001
From: samrose <samuel.rose@gmail.com>
Date: Fri, 19 Sep 2025 11:43:57 -0400
Subject: [PATCH 11/22] fix: integrtion tests

---
 nix/ext/tests/default.nix | 1 -
 nix/tests/timescaledb.nix | 8 ++++----
 2 files changed, 4 insertions(+), 5 deletions(-)

diff --git a/nix/ext/tests/default.nix b/nix/ext/tests/default.nix
index 878b01933..afea82fc8 100644
--- a/nix/ext/tests/default.nix
+++ b/nix/ext/tests/default.nix
@@ -186,7 +186,6 @@ builtins.listToAttrs (
       "index_advisor"
       "pg_cron"
       "pg_net"
-      "timescaledb"
       "vector"
       "wrappers"
     ]
diff --git a/nix/tests/timescaledb.nix b/nix/tests/timescaledb.nix
index 2978055e7..ab9e481b0 100644
--- a/nix/tests/timescaledb.nix
+++ b/nix/tests/timescaledb.nix
@@ -90,11 +90,11 @@ self.inputs.nixpkgs.lib.nixos.runTest {
                   installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
                   assert installed_version == version, f"Expected timescaledb version {version}, but found {installed_version}"
 
-          start_all()
+      start_all()
 
-          server.wait_for_unit("multi-user.target")
-          server.wait_for_unit("postgresql.service")
+      server.wait_for_unit("multi-user.target")
+      server.wait_for_unit("postgresql.service")
 
-          check_upgrade_path()
+      check_upgrade_path()
     '';
 }

From 5466049c331d0fc6a558cbffd754aae918bd0cb3 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Jean-Fran=C3=A7ois=20Roche?= <jfroche@pyxel.be>
Date: Fri, 19 Sep 2025 17:57:21 +0200
Subject: [PATCH 12/22] Move timescaledb nixos test to nix/ext/tests

---
 nix/{ => ext}/tests/timescaledb.nix | 0
 1 file changed, 0 insertions(+), 0 deletions(-)
 rename nix/{ => ext}/tests/timescaledb.nix (100%)

diff --git a/nix/tests/timescaledb.nix b/nix/ext/tests/timescaledb.nix
similarity index 100%
rename from nix/tests/timescaledb.nix
rename to nix/ext/tests/timescaledb.nix

From f92194142cb34e5b5970b1ed28c37160aaaa9b10 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Fri, 19 Sep 2025 13:35:54 -0400
Subject: [PATCH 13/22] chore: bump for test

---
 ansible/vars.yml | 6 +++---
 1 file changed, 3 insertions(+), 3 deletions(-)

diff --git a/ansible/vars.yml b/ansible/vars.yml
index a32c56d7a..562804777 100644
--- a/ansible/vars.yml
+++ b/ansible/vars.yml
@@ -9,9 +9,9 @@ postgres_major:
 
 # Full version strings for each major version
 postgres_release:
-  postgresorioledb-17: "17.5.1.026-orioledb"
-  postgres17: "17.6.1.005"
-  postgres15: "15.14.1.005"
+  postgresorioledb-17: "17.5.1.026-orioledb-timescale-1"
+  postgres17: "17.6.1.005-timescale-1"
+  postgres15: "15.14.1.005-timescale-1"
 
 # Non Postgres Extensions
 pgbouncer_release: "1.19.0"

From 90c5e4bd17892eb6eaa5cbf0c19bc51ec3001eda Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Mon, 22 Sep 2025 11:38:26 -0400
Subject: [PATCH 14/22] fix: need to also handle timescaledb-loader

---
 nix/packages/switch-ext-version.nix | 8 ++++++++
 1 file changed, 8 insertions(+)

diff --git a/nix/packages/switch-ext-version.nix b/nix/packages/switch-ext-version.nix
index 1b0354a26..e100197b8 100644
--- a/nix/packages/switch-ext-version.nix
+++ b/nix/packages/switch-ext-version.nix
@@ -54,6 +54,14 @@ writeShellApplication {
     # Update library symlink
     ln -sfnv "$EXT_LIB_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME${postgresql.dlSuffix}"
 
+    # Handle timescaledb-loader symlink (specific to timescaledb)
+    if [ "$EXT_NAME" = "timescaledb" ]; then
+      EXT_LOADER_TO_USE="$EXT_WRAPPER_LIB/$EXT_NAME-loader-$VERSION${postgresql.dlSuffix}"
+      if [ -f "$EXT_LOADER_TO_USE" ]; then
+        ln -sfnv "$EXT_LOADER_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME-loader${postgresql.dlSuffix}"
+      fi
+    fi
+
     # Update control file
     EXT_WRAPPER_SHARE="$EXT_WRAPPER/share/postgresql/extension"
     echo "default_version = '$VERSION'" > "$EXT_WRAPPER_SHARE/$EXT_NAME.control"

From 7cce2c249f90e4378956ad262dc68d8bf908def6 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Mon, 22 Sep 2025 14:17:06 -0400
Subject: [PATCH 15/22] chore: bump version for fix

---
 ansible/vars.yml | 6 +++---
 1 file changed, 3 insertions(+), 3 deletions(-)

diff --git a/ansible/vars.yml b/ansible/vars.yml
index 562804777..10cd48a79 100644
--- a/ansible/vars.yml
+++ b/ansible/vars.yml
@@ -9,9 +9,9 @@ postgres_major:
 
 # Full version strings for each major version
 postgres_release:
-  postgresorioledb-17: "17.5.1.026-orioledb-timescale-1"
-  postgres17: "17.6.1.005-timescale-1"
-  postgres15: "15.14.1.005-timescale-1"
+  postgresorioledb-17: "17.5.1.026-orioledb-timescale-2"
+  postgres17: "17.6.1.005-timescale-2"
+  postgres15: "15.14.1.005-timescale-2"
 
 # Non Postgres Extensions
 pgbouncer_release: "1.19.0"

From 5cbce8f080be38e9baef75e576d8ab33aa7bb981 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Mon, 22 Sep 2025 15:31:47 -0400
Subject: [PATCH 16/22] fix: didn't need "loader"

---
 nix/ext/timescaledb.nix             | 4 ++--
 nix/packages/switch-ext-version.nix | 8 --------
 2 files changed, 2 insertions(+), 10 deletions(-)

diff --git a/nix/ext/timescaledb.nix b/nix/ext/timescaledb.nix
index 5fea738a7..2c1c7c271 100644
--- a/nix/ext/timescaledb.nix
+++ b/nix/ext/timescaledb.nix
@@ -66,7 +66,7 @@ let
 
         # Rename the loader to be version-specific
         if [ -f $out/lib/timescaledb${postgresql.dlSuffix} ]; then
-          mv $out/lib/timescaledb${postgresql.dlSuffix} $out/lib/timescaledb-loader-${version}${postgresql.dlSuffix}
+          mv $out/lib/timescaledb${postgresql.dlSuffix} $out/lib/timescaledb-${version}${postgresql.dlSuffix}
         fi
 
         # The versioned library (timescaledb-VERSION.so) is already correctly named
@@ -111,7 +111,7 @@ buildEnv {
     } > $out/share/postgresql/extension/${pname}.control
 
     # Create symlink for the loader
-    ln -sfn ${pname}-loader-${latestVersion}${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
+    ln -sfn ${pname}-${latestVersion}${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
 
     # The versioned library symlink (timescaledb-VERSION.so files are already in place)
 
diff --git a/nix/packages/switch-ext-version.nix b/nix/packages/switch-ext-version.nix
index e100197b8..1b0354a26 100644
--- a/nix/packages/switch-ext-version.nix
+++ b/nix/packages/switch-ext-version.nix
@@ -54,14 +54,6 @@ writeShellApplication {
     # Update library symlink
     ln -sfnv "$EXT_LIB_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME${postgresql.dlSuffix}"
 
-    # Handle timescaledb-loader symlink (specific to timescaledb)
-    if [ "$EXT_NAME" = "timescaledb" ]; then
-      EXT_LOADER_TO_USE="$EXT_WRAPPER_LIB/$EXT_NAME-loader-$VERSION${postgresql.dlSuffix}"
-      if [ -f "$EXT_LOADER_TO_USE" ]; then
-        ln -sfnv "$EXT_LOADER_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME-loader${postgresql.dlSuffix}"
-      fi
-    fi
-
     # Update control file
     EXT_WRAPPER_SHARE="$EXT_WRAPPER/share/postgresql/extension"
     echo "default_version = '$VERSION'" > "$EXT_WRAPPER_SHARE/$EXT_NAME.control"

From bdfc3e10f6d125029164d3d9b25b2d7907fe8f09 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Mon, 22 Sep 2025 15:34:01 -0400
Subject: [PATCH 17/22] chore: bump version for testing

---
 ansible/vars.yml | 6 +++---
 1 file changed, 3 insertions(+), 3 deletions(-)

diff --git a/ansible/vars.yml b/ansible/vars.yml
index 10cd48a79..bdaa0b48d 100644
--- a/ansible/vars.yml
+++ b/ansible/vars.yml
@@ -9,9 +9,9 @@ postgres_major:
 
 # Full version strings for each major version
 postgres_release:
-  postgresorioledb-17: "17.5.1.026-orioledb-timescale-2"
-  postgres17: "17.6.1.005-timescale-2"
-  postgres15: "15.14.1.005-timescale-2"
+  postgresorioledb-17: "17.5.1.026-orioledb-timescale-3"
+  postgres17: "17.6.1.005-timescale-3"
+  postgres15: "15.14.1.005-timescale-3"
 
 # Non Postgres Extensions
 pgbouncer_release: "1.19.0"

From c0e5f3fcf93af5f93f4bae8497b8948fb364f5b0 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Mon, 22 Sep 2025 16:16:13 -0400
Subject: [PATCH 18/22] fix: does need loader

---
 nix/ext/timescaledb.nix | 19 +++++++++----------
 1 file changed, 9 insertions(+), 10 deletions(-)

diff --git a/nix/ext/timescaledb.nix b/nix/ext/timescaledb.nix
index 2c1c7c271..4c51aadb1 100644
--- a/nix/ext/timescaledb.nix
+++ b/nix/ext/timescaledb.nix
@@ -59,14 +59,13 @@ let
         # Run cmake install first
         cmake --install . --prefix=$out
 
-        # TimescaleDB has two libraries:
-        # 1. timescaledb.so (loader)
-        # 2. timescaledb-VERSION.so (actual extension)
-        # Both need to be handled for multi-version support
+        # TimescaleDB creates two libraries:
+        # 1. timescaledb.so (loader) -> rename to timescaledb-<version>-loader.so
+        # 2. timescaledb-<version>.so (actual extension) -> keep as is
 
-        # Rename the loader to be version-specific
+        # Rename the loader library to be version-specific
         if [ -f $out/lib/timescaledb${postgresql.dlSuffix} ]; then
-          mv $out/lib/timescaledb${postgresql.dlSuffix} $out/lib/timescaledb-${version}${postgresql.dlSuffix}
+          mv $out/lib/timescaledb${postgresql.dlSuffix} $out/lib/timescaledb-${version}-loader${postgresql.dlSuffix}
         fi
 
         # The versioned library (timescaledb-VERSION.so) is already correctly named
@@ -110,12 +109,12 @@ buildEnv {
       cat $out/share/postgresql/extension/${pname}--${latestVersion}.control
     } > $out/share/postgresql/extension/${pname}.control
 
-    # Create symlink for the loader
-    ln -sfn ${pname}-${latestVersion}${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
+    # Create symlink from the latest versioned loader to timescaledb.so
+    ln -sfn ${pname}-${latestVersion}-loader${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
 
-    # The versioned library symlink (timescaledb-VERSION.so files are already in place)
+    # The versioned extension libraries (timescaledb-VERSION.so) are already in place
 
-    # checks - adjust count since we have both loader and versioned files
+    # checks - we should have loader files and versioned extension files
     (set -x
        test "$(ls -A $out/lib/${pname}*${postgresql.dlSuffix} | wc -l)" -gt 0
     )

From 33d6a4f97b89a2ceb2feaa39335818dc3c5c48ec Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Jean-Fran=C3=A7ois=20Roche?= <jfroche@pyxel.be>
Date: Mon, 22 Sep 2025 20:44:35 +0200
Subject: [PATCH 19/22] feat: switch both timescaledb and its loader when
 switching versions

Also reuse default tests defined in lib.py to test extension upgrade
paths and switching extension versions.
---
 nix/ext/tests/lib.py                |  6 +--
 nix/ext/tests/timescaledb.nix       | 60 +++++++++--------------------
 nix/ext/timescaledb.nix             | 21 ++++++++--
 nix/packages/switch-ext-version.nix |  6 +++
 4 files changed, 45 insertions(+), 48 deletions(-)

diff --git a/nix/ext/tests/lib.py b/nix/ext/tests/lib.py
index 1e3956c9b..35c5b0e04 100644
--- a/nix/ext/tests/lib.py
+++ b/nix/ext/tests/lib.py
@@ -147,7 +147,7 @@ def check_switch_extension_with_background_worker(
             )
         last_version = available_versions[-1]
         assert ext_version.endswith(
-            f"{self.extension_name}-{last_version}.so"
+            f"{last_version}.so"
         ), f"Expected {self.extension_name} version {last_version}, but found {ext_version}"
 
         # Switch to the first version
@@ -157,7 +157,7 @@ def check_switch_extension_with_background_worker(
         # Check that we are using the first version now
         ext_version = self.vm.succeed(f"readlink -f {extension_lib_path}").strip()
         assert ext_version.endswith(
-            f"{self.extension_name}-{first_version}.so"
+            f"{first_version}.so"
         ), f"Expected {self.extension_name} version {first_version}, but found {ext_version}"
 
         # Switch to the first version
@@ -165,5 +165,5 @@ def check_switch_extension_with_background_worker(
         # Check that we are using the last version now
         ext_version = self.vm.succeed(f"readlink -f {extension_lib_path}").strip()
         assert ext_version.endswith(
-            f"{self.extension_name}-{last_version}.so"
+            f"{last_version}.so"
         ), f"Expected {self.extension_name} version {last_version}, but found {ext_version}"
diff --git a/nix/ext/tests/timescaledb.nix b/nix/ext/tests/timescaledb.nix
index ab9e481b0..597fe9e0d 100644
--- a/nix/ext/tests/timescaledb.nix
+++ b/nix/ext/tests/timescaledb.nix
@@ -1,17 +1,16 @@
 { self, pkgs }:
 let
+  pname = "timescaledb";
   inherit (pkgs) lib;
   installedExtension =
-    postgresMajorVersion:
-    self.packages.${pkgs.system}."psql_${postgresMajorVersion}/exts/timescaledb-all";
+    postgresMajorVersion: self.packages.${pkgs.system}."psql_${postgresMajorVersion}/exts/${pname}-all";
   versions = (installedExtension "15").versions;
-  firstVersion = lib.head versions;
   postgresqlWithExtension =
     postgresql:
     let
       majorVersion = lib.versions.major postgresql.version;
       pkg = pkgs.buildEnv {
-        name = "postgresql-${majorVersion}-timescaledb";
+        name = "postgresql-${majorVersion}-${pname}";
         paths = [
           postgresql
           postgresql.lib
@@ -36,6 +35,7 @@ let
       };
     in
     pkg;
+  psql_15 = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15;
 in
 self.inputs.nixpkgs.lib.nixos.runTest {
   name = "timescaledb";
@@ -43,58 +43,36 @@ self.inputs.nixpkgs.lib.nixos.runTest {
   nodes.server =
     { ... }:
     {
-      virtualisation = {
-        forwardPorts = [
-          {
-            from = "host";
-            host.port = 13022;
-            guest.port = 22;
-          }
-        ];
-      };
-      services.openssh = {
-        enable = true;
-      };
-      users.users.root.openssh.authorizedKeys.keys = [
-        "ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIArkmq6Th79Z4klW6Urgi4phN8yq769/l/10jlE00tU9"
-      ];
-
       services.postgresql = {
         enable = true;
-        package = postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15;
+        package = (postgresqlWithExtension psql_15);
         settings = {
           shared_preload_libraries = "timescaledb";
         };
       };
-
-      specialisation.postgresql15.configuration = {
-        services.postgresql = {
-          package = lib.mkForce (postgresqlWithExtension self.packages.${pkgs.system}.postgresql_15);
-        };
-      };
     };
   testScript =
     { ... }:
     ''
-      def run_sql(query):
-          return server.succeed(f"""sudo -u postgres psql -t -A -F\",\" -c \"{query}\" """).strip()
-
-      def check_upgrade_path():
-          with subtest("Check timescaledb upgrade path"):
-              server.succeed("sudo -u postgres psql -c 'DROP EXTENSION IF EXISTS timescaledb;'")
-              run_sql(r"""CREATE EXTENSION timescaledb WITH VERSION \"${firstVersion}\";""")
-              installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
-              assert installed_version == "${firstVersion}", f"Expected timescaledb version ${firstVersion}, but found {installed_version}"
-              for version in [${lib.concatStringsSep ", " (map (s: ''"${s}"'') versions)}][1:]:
-                  run_sql(f"""ALTER EXTENSION timescaledb UPDATE TO '{version}';""")
-                  installed_version = run_sql(r"""SELECT extversion FROM pg_extension WHERE extname = 'timescaledb';""")
-                  assert installed_version == version, f"Expected timescaledb version {version}, but found {installed_version}"
+      ${builtins.readFile ./lib.py}
 
       start_all()
 
       server.wait_for_unit("multi-user.target")
       server.wait_for_unit("postgresql.service")
 
-      check_upgrade_path()
+      versions = {
+        "15": [${lib.concatStringsSep ", " (map (s: ''"${s}"'') versions)}],
+      }
+      extension_name = "${pname}"
+      support_upgrade = True
+
+      test = PostgresExtensionTest(server, extension_name, versions, support_upgrade)
+
+      with subtest("Check upgrade path with postgresql 15"):
+        test.check_upgrade_path("15")
+
+      with subtest("Test switch_${pname}_version"):
+        test.check_switch_extension_with_background_worker(Path("${psql_15}/lib/${pname}.so"), "15")
     '';
 }
diff --git a/nix/ext/timescaledb.nix b/nix/ext/timescaledb.nix
index 4c51aadb1..2ac328306 100644
--- a/nix/ext/timescaledb.nix
+++ b/nix/ext/timescaledb.nix
@@ -9,6 +9,8 @@
   buildEnv,
   makeWrapper,
   switch-ext-version,
+  coreutils,
+  writeShellApplication,
 }:
 
 let
@@ -65,7 +67,7 @@ let
 
         # Rename the loader library to be version-specific
         if [ -f $out/lib/timescaledb${postgresql.dlSuffix} ]; then
-          mv $out/lib/timescaledb${postgresql.dlSuffix} $out/lib/timescaledb-${version}-loader${postgresql.dlSuffix}
+          mv $out/lib/timescaledb${postgresql.dlSuffix} $out/lib/timescaledb-loader-${version}${postgresql.dlSuffix}
         fi
 
         # The versioned library (timescaledb-VERSION.so) is already correctly named
@@ -98,6 +100,16 @@ let
   packages = builtins.attrValues (
     lib.mapAttrs (name: value: build name value.hash (value.revision or name)) supportedVersions
   );
+  switch-timescaledb-loader = writeShellApplication {
+    name = "switch_timescaledb_loader";
+    runtimeInputs = [ coreutils ];
+    text = ''
+      EXT_LOADER_TO_USE="$EXT_WRAPPER_LIB/$EXT_NAME-loader-$VERSION${postgresql.dlSuffix}"
+      if [ -f "$EXT_LOADER_TO_USE" ]; then
+        ln -sfnv "$EXT_LOADER_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME-loader${postgresql.dlSuffix}"
+      fi
+    '';
+  };
 in
 buildEnv {
   name = pname;
@@ -110,7 +122,7 @@ buildEnv {
     } > $out/share/postgresql/extension/${pname}.control
 
     # Create symlink from the latest versioned loader to timescaledb.so
-    ln -sfn ${pname}-${latestVersion}-loader${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
+    ln -sfn ${pname}-loader-${latestVersion}${postgresql.dlSuffix} $out/lib/${pname}${postgresql.dlSuffix}
 
     # The versioned extension libraries (timescaledb-VERSION.so) are already in place
 
@@ -119,13 +131,14 @@ buildEnv {
        test "$(ls -A $out/lib/${pname}*${postgresql.dlSuffix} | wc -l)" -gt 0
     )
     makeWrapper ${lib.getExe switch-ext-version} $out/bin/switch_timescaledb_version \
-      --prefix EXT_WRAPPER : "$out" --prefix EXT_NAME : "${pname}"
-
+      --prefix EXT_WRAPPER : "$out" --prefix EXT_NAME : "${pname}" --prefix EXTRA_STEPS : ${lib.getExe switch-timescaledb-loader}
   '';
+
   pathsToLink = [
     "/lib"
     "/share/postgresql/extension"
   ];
+
   passthru = {
     inherit versions numberOfVersions switch-ext-version;
     pname = "${pname}-all";
diff --git a/nix/packages/switch-ext-version.nix b/nix/packages/switch-ext-version.nix
index 1b0354a26..e3d211bbb 100644
--- a/nix/packages/switch-ext-version.nix
+++ b/nix/packages/switch-ext-version.nix
@@ -54,6 +54,12 @@ writeShellApplication {
     # Update library symlink
     ln -sfnv "$EXT_LIB_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME${postgresql.dlSuffix}"
 
+    # Handle extension specific steps
+    if [ -x "''${EXTRA_STEPS:-}" ]; then
+      #shellcheck disable=SC1090
+      source "''${EXTRA_STEPS}"
+    fi
+
     # Update control file
     EXT_WRAPPER_SHARE="$EXT_WRAPPER/share/postgresql/extension"
     echo "default_version = '$VERSION'" > "$EXT_WRAPPER_SHARE/$EXT_NAME.control"

From eb7407a061c262f815ffe0d9a0b532fbf531926d Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Mon, 22 Sep 2025 18:53:02 -0400
Subject: [PATCH 20/22] chore: bump to test

---
 ansible/vars.yml | 6 +++---
 1 file changed, 3 insertions(+), 3 deletions(-)

diff --git a/ansible/vars.yml b/ansible/vars.yml
index bdaa0b48d..54dcda833 100644
--- a/ansible/vars.yml
+++ b/ansible/vars.yml
@@ -9,9 +9,9 @@ postgres_major:
 
 # Full version strings for each major version
 postgres_release:
-  postgresorioledb-17: "17.5.1.026-orioledb-timescale-3"
-  postgres17: "17.6.1.005-timescale-3"
-  postgres15: "15.14.1.005-timescale-3"
+  postgresorioledb-17: "17.5.1.026-orioledb-timescale-4"
+  postgres17: "17.6.1.005-timescale-4"
+  postgres15: "15.14.1.005-timescale-4"
 
 # Non Postgres Extensions
 pgbouncer_release: "1.19.0"

From c7604f1aa810aa8626103048f1ee1368a4ef3bae Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Tue, 23 Sep 2025 10:19:49 -0400
Subject: [PATCH 21/22] fix: must symlink to timescaledb.so on switch

---
 ansible/vars.yml        | 6 +++---
 nix/ext/timescaledb.nix | 2 +-
 2 files changed, 4 insertions(+), 4 deletions(-)

diff --git a/ansible/vars.yml b/ansible/vars.yml
index 54dcda833..2394e3f04 100644
--- a/ansible/vars.yml
+++ b/ansible/vars.yml
@@ -9,9 +9,9 @@ postgres_major:
 
 # Full version strings for each major version
 postgres_release:
-  postgresorioledb-17: "17.5.1.026-orioledb-timescale-4"
-  postgres17: "17.6.1.005-timescale-4"
-  postgres15: "15.14.1.005-timescale-4"
+  postgresorioledb-17: "17.5.1.026-orioledb-timescale-5"
+  postgres17: "17.6.1.005-timescale-5"
+  postgres15: "15.14.1.005-timescale-5"
 
 # Non Postgres Extensions
 pgbouncer_release: "1.19.0"
diff --git a/nix/ext/timescaledb.nix b/nix/ext/timescaledb.nix
index 2ac328306..a58e8e2b4 100644
--- a/nix/ext/timescaledb.nix
+++ b/nix/ext/timescaledb.nix
@@ -106,7 +106,7 @@ let
     text = ''
       EXT_LOADER_TO_USE="$EXT_WRAPPER_LIB/$EXT_NAME-loader-$VERSION${postgresql.dlSuffix}"
       if [ -f "$EXT_LOADER_TO_USE" ]; then
-        ln -sfnv "$EXT_LOADER_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME-loader${postgresql.dlSuffix}"
+        ln -sfnv "$EXT_LOADER_TO_USE" "$EXT_WRAPPER_LIB/$EXT_NAME${postgresql.dlSuffix}"
       fi
     '';
   };

From 24d7bc25a849ea4116a007390711130970245022 Mon Sep 17 00:00:00 2001
From: Sam Rose <samuel@supabase.io>
Date: Tue, 23 Sep 2025 11:40:39 -0400
Subject: [PATCH 22/22] chore: bump for release

---
 ansible/vars.yml | 6 +++---
 1 file changed, 3 insertions(+), 3 deletions(-)

diff --git a/ansible/vars.yml b/ansible/vars.yml
index 2394e3f04..742527b7f 100644
--- a/ansible/vars.yml
+++ b/ansible/vars.yml
@@ -9,9 +9,9 @@ postgres_major:
 
 # Full version strings for each major version
 postgres_release:
-  postgresorioledb-17: "17.5.1.026-orioledb-timescale-5"
-  postgres17: "17.6.1.005-timescale-5"
-  postgres15: "15.14.1.005-timescale-5"
+  postgresorioledb-17: "17.5.1.027-orioledb"
+  postgres17: "17.6.1.006"
+  postgres15: "15.14.1.006"
 
 # Non Postgres Extensions
 pgbouncer_release: "1.19.0"