diff --git a/webview-ui/src/components/history/HistoryView.tsx b/webview-ui/src/components/history/HistoryView.tsx
index 1189cffc0e2..ea5c5cf6574 100644
--- a/webview-ui/src/components/history/HistoryView.tsx
+++ b/webview-ui/src/components/history/HistoryView.tsx
@@ -227,7 +227,12 @@ const HistoryView = ({ onDone }: HistoryViewProps) => {
 											title="Delete Task"
 											onClick={(e) => {
 												e.stopPropagation()
-												setDeleteTaskId(item.id)
+												if (e.shiftKey) {
+													// directly delete without prompting if shift is pressed
+													vscode.postMessage({ type: "deleteTaskWithId", text: item.id })
+												} else {
+													setDeleteTaskId(item.id)
+												}
 											}}>
 											<span className="codicon codicon-trash" />
 											{item.size && prettyBytes(item.size)}
diff --git a/webview-ui/src/components/history/__tests__/HistoryView.test.tsx b/webview-ui/src/components/history/__tests__/HistoryView.test.tsx
index 12b0181af6b..51e197713d8 100644
--- a/webview-ui/src/components/history/__tests__/HistoryView.test.tsx
+++ b/webview-ui/src/components/history/__tests__/HistoryView.test.tsx
@@ -135,26 +135,54 @@ describe("HistoryView", () => {
 		})
 	})
 
-	it("handles task deletion", async () => {
-		const onDone = jest.fn()
-		render(<HistoryView onDone={onDone} />)
+	describe("task deletion", () => {
+		it("shows confirmation dialog on regular click", () => {
+			const onDone = jest.fn()
+			render(<HistoryView onDone={onDone} />)
+
+			// Find and hover over first task
+			const taskContainer = screen.getByTestId("virtuoso-item-1")
+			fireEvent.mouseEnter(taskContainer)
+
+			// Click delete button to open confirmation dialog
+			const deleteButton = within(taskContainer).getByTitle("Delete Task")
+			fireEvent.click(deleteButton)
+
+			// Verify dialog is shown
+			const dialog = screen.getByRole("alertdialog")
+			expect(dialog).toBeInTheDocument()
+
+			// Find and click the confirm delete button in the dialog
+			const confirmDeleteButton = within(dialog).getByRole("button", { name: /delete/i })
+			fireEvent.click(confirmDeleteButton)
+
+			// Verify vscode message was sent
+			expect(vscode.postMessage).toHaveBeenCalledWith({
+				type: "deleteTaskWithId",
+				text: "1",
+			})
+		})
 
-		// Find and hover over first task
-		const taskContainer = screen.getByTestId("virtuoso-item-1")
-		fireEvent.mouseEnter(taskContainer)
+		it("deletes immediately on shift-click without confirmation", () => {
+			const onDone = jest.fn()
+			render(<HistoryView onDone={onDone} />)
 
-		// Click delete button to open confirmation dialog
-		const deleteButton = within(taskContainer).getByTitle("Delete Task")
-		fireEvent.click(deleteButton)
+			// Find and hover over first task
+			const taskContainer = screen.getByTestId("virtuoso-item-1")
+			fireEvent.mouseEnter(taskContainer)
 
-		// Find and click the confirm delete button in the dialog
-		const confirmDeleteButton = screen.getByRole("button", { name: /delete/i })
-		fireEvent.click(confirmDeleteButton)
+			// Shift-click delete button
+			const deleteButton = within(taskContainer).getByTitle("Delete Task")
+			fireEvent.click(deleteButton, { shiftKey: true })
 
-		// Verify vscode message was sent
-		expect(vscode.postMessage).toHaveBeenCalledWith({
-			type: "deleteTaskWithId",
-			text: "1",
+			// Verify no dialog is shown
+			expect(screen.queryByRole("alertdialog")).not.toBeInTheDocument()
+
+			// Verify vscode message was sent
+			expect(vscode.postMessage).toHaveBeenCalledWith({
+				type: "deleteTaskWithId",
+				text: "1",
+			})
 		})
 	})