diff --git a/src/CONST/index.ts b/src/CONST/index.ts
index 975cbd0052a7..c4babbaa864d 100755
--- a/src/CONST/index.ts
+++ b/src/CONST/index.ts
@@ -1682,6 +1682,9 @@ const CONST = {
         CONTEXT_POLICIES: 'Policies',
         TAG_ACTIVE_POLICY: 'active_policy_id',
         TAG_NUDGE_MIGRATION_COHORT: 'nudge_migration_cohort',
+        TAG_AUTHENTICATION_FUNCTION: 'authentication_function',
+        TAG_AUTHENTICATION_ERROR_TYPE: 'authentication_error_type',
+        TAG_AUTHENTICATION_JSON_CODE: 'authentication_json_code',
         // Span names
         SPAN_OPEN_REPORT: 'ManualOpenReport',
         SPAN_APP_STARTUP: 'ManualAppStartup',
diff --git a/src/libs/Authentication.ts b/src/libs/Authentication.ts
index 77f19dd6b3ef..51dcf99b42cd 100644
--- a/src/libs/Authentication.ts
+++ b/src/libs/Authentication.ts
@@ -15,6 +15,7 @@ import {post} from './Network';
 import {getCredentials, hasReadRequiredDataFromStorage, setAuthToken, setIsAuthenticating} from './Network/NetworkStore';
 import requireParameters from './requireParameters';
 import {checkIfShouldUseNewPartnerName} from './SessionUtils';
+import trackAuthenticationError from './telemetry/trackAuthenticationError';
 
 type Parameters = {
     useExpensifyLogin?: boolean;
@@ -62,6 +63,12 @@ function Authenticate(parameters: Parameters): Promise<Response | void> {
         requireParameters(['partnerName', 'partnerPassword', 'partnerUserID', 'partnerUserSecret'], parameters, commandName);
     } catch (error) {
         const errorMessage = (error as Error).message;
+        trackAuthenticationError(error as Error, {
+            errorType: 'missing_params',
+            functionName: 'Authenticate',
+            commandName,
+            providedParameters: Object.keys(parameters),
+        });
         Log.hmmm('Redirecting to Sign In because we failed to reauthenticate', {
             error: errorMessage,
         });
@@ -147,12 +154,27 @@ function reauthenticate(command = ''): Promise<boolean> {
             if (response.jsonCode === CONST.JSON_CODE.UNABLE_TO_RETRY) {
                 // When a fetch() fails due to a network issue and an error is thrown we won't log the user out. Most likely they
                 // have a spotty connection and will need to retry reauthenticate when they come back online. Error so it can be handled by the retry mechanism.
-                throw new Error('Unable to retry Authenticate request');
+                const error = new Error('Unable to retry Authenticate request');
+                trackAuthenticationError(error, {
+                    errorType: 'network_retry',
+                    functionName: 'reauthenticate',
+                    jsonCode: response.jsonCode,
+                    command,
+                });
+                throw error;
             }
 
             // If authentication fails and we are online then log the user out
             if (response.jsonCode !== 200) {
                 const errorMessage = getAuthenticateErrorMessage(response);
+
+                trackAuthenticationError(new Error('Authentication failed'), {
+                    errorType: 'auth_failure',
+                    functionName: 'reauthenticate',
+                    jsonCode: response.jsonCode,
+                    command,
+                    errorMessage,
+                });
                 setIsAuthenticating(false);
                 Log.hmmm('Redirecting to Sign In because we failed to reauthenticate', {
                     command,
diff --git a/src/libs/telemetry/trackAuthenticationError.ts b/src/libs/telemetry/trackAuthenticationError.ts
new file mode 100644
index 000000000000..08438b776e94
--- /dev/null
+++ b/src/libs/telemetry/trackAuthenticationError.ts
@@ -0,0 +1,45 @@
+import * as Sentry from '@sentry/react-native';
+import CONST from '@src/CONST';
+
+type AuthenticationFunction = 'Authenticate' | 'reauthenticate';
+type AuthenticationErrorType = 'missing_params' | 'network_retry' | 'auth_failure';
+
+type AuthenticationErrorContext = {
+    errorType: AuthenticationErrorType;
+    functionName: AuthenticationFunction;
+    jsonCode?: number | string;
+    command?: string;
+    commandName?: string;
+    errorMessage?: string;
+    providedParameters?: string[];
+};
+
+/**
+ * Track authentication errors in Sentry with extra context.
+ *
+ * @param error - The error object to capture
+ * @param context - Additional context about the authentication error
+ */
+function trackAuthenticationError(error: Error, context: AuthenticationErrorContext): void {
+    const {errorType, functionName, jsonCode, command, commandName, errorMessage, providedParameters} = context;
+
+    const tags: Record<string, string> = {
+        [CONST.TELEMETRY.TAG_AUTHENTICATION_FUNCTION]: functionName,
+        [CONST.TELEMETRY.TAG_AUTHENTICATION_ERROR_TYPE]: errorType,
+    };
+
+    if (jsonCode !== undefined) {
+        tags[CONST.TELEMETRY.TAG_AUTHENTICATION_JSON_CODE] = String(jsonCode);
+    }
+
+    const extra: Record<string, unknown> = {
+        ...(command && {command}),
+        ...(commandName && {commandName}),
+        ...(errorMessage && {errorMessage}),
+        ...(providedParameters && {providedParameters}),
+    };
+
+    Sentry.captureException(error, {tags, extra});
+}
+
+export default trackAuthenticationError;