diff --git a/src/vs/workbench/contrib/terminal/common/terminal.ts b/src/vs/workbench/contrib/terminal/common/terminal.ts
index f113bb4360b..0953ecef87a 100644
--- a/src/vs/workbench/contrib/terminal/common/terminal.ts
+++ b/src/vs/workbench/contrib/terminal/common/terminal.ts
@@ -452,6 +452,7 @@ export const enum TerminalCommandId {
 	FocusNext = 'workbench.action.terminal.focusNext',
 	FocusPrevious = 'workbench.action.terminal.focusPrevious',
 	Paste = 'workbench.action.terminal.paste',
+	PastePwsh = 'workbench.action.terminal.pastePwsh',
 	PasteSelection = 'workbench.action.terminal.pasteSelection',
 	SelectDefaultProfile = 'workbench.action.terminal.selectDefaultShell',
 	RunSelectedText = 'workbench.action.terminal.runSelectedText',
@@ -522,6 +523,7 @@ export const DEFAULT_COMMANDS_TO_SKIP_SHELL: string[] = [
 	TerminalCommandId.New,
 	TerminalCommandId.NewInNewWindow,
 	TerminalCommandId.Paste,
+	TerminalCommandId.PastePwsh,
 	TerminalCommandId.PasteSelection,
 	TerminalCommandId.ResizePaneDown,
 	TerminalCommandId.ResizePaneLeft,
diff --git a/src/vs/workbench/contrib/terminalContrib/sendSequence/browser/terminal.sendSequence.contribution.ts b/src/vs/workbench/contrib/terminalContrib/sendSequence/browser/terminal.sendSequence.contribution.ts
index a855b30e039..06022ea8352 100644
--- a/src/vs/workbench/contrib/terminalContrib/sendSequence/browser/terminal.sendSequence.contribution.ts
+++ b/src/vs/workbench/contrib/terminalContrib/sendSequence/browser/terminal.sendSequence.contribution.ts
@@ -9,6 +9,8 @@ import { isIOS, isMacintosh, isWindows } from '../../../../../base/common/platfo
 import { isObject, isString } from '../../../../../base/common/types.js';
 import { localize, localize2 } from '../../../../../nls.js';
 import { CONTEXT_ACCESSIBILITY_MODE_ENABLED } from '../../../../../platform/accessibility/common/accessibility.js';
+import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
+import { ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { ContextKeyExpr, type ContextKeyExpression } from '../../../../../platform/contextkey/common/contextkey.js';
 import type { ServicesAccessor } from '../../../../../platform/instantiation/common/instantiation.js';
 import { KeybindingsRegistry, KeybindingWeight, type IKeybindings } from '../../../../../platform/keybinding/common/keybindingsRegistry.js';
@@ -19,6 +21,7 @@ import { IConfigurationResolverService } from '../../../../services/configuratio
 import { IHistoryService } from '../../../../services/history/common/history.js';
 import { ITerminalService } from '../../../terminal/browser/terminal.js';
 import { registerTerminalAction } from '../../../terminal/browser/terminalActions.js';
+import { TerminalCommandId } from '../../../terminal/common/terminal.js';
 import { TerminalContextKeys, TerminalContextKeyStrings } from '../../../terminal/common/terminalContextKey.js';
 
 export const enum TerminalSendSequenceCommandId {
@@ -126,10 +129,25 @@ const enum Constants {
 // shell, this gets handled by PSReadLine which properly handles multi-line pastes. This is
 // disabled in accessibility mode as PowerShell does not run PSReadLine when it detects a screen
 // reader. This works even when clipboard.readText is not supported.
+//
+// When the clipboard contains a VS Code file resource but no text, PSReadLine
+// cannot see it (it only reads CF_UNICODETEXT from the Win32 clipboard), so we delegate to the
+// standard paste command instead.
 if (isWindows) {
-	registerSendSequenceKeybinding(String.fromCharCode('V'.charCodeAt(0) - Constants.CtrlLetterOffset), { // ctrl+v
+	const ctrlV = String.fromCharCode('V'.charCodeAt(0) - Constants.CtrlLetterOffset);
+	KeybindingsRegistry.registerCommandAndKeybindingRule({
+		id: TerminalCommandId.PastePwsh,
+		weight: KeybindingWeight.WorkbenchContrib,
 		when: ContextKeyExpr.and(TerminalContextKeys.focus, ContextKeyExpr.equals(TerminalContextKeyStrings.ShellType, GeneralShellType.PowerShell), CONTEXT_ACCESSIBILITY_MODE_ENABLED.negate()),
-		primary: KeyMod.CtrlCmd | KeyCode.KeyV
+		primary: KeyMod.CtrlCmd | KeyCode.KeyV,
+		handler: async accessor => {
+			const clipboardService = accessor.get(IClipboardService);
+			const commandService = accessor.get(ICommandService);
+			if (!await clipboardService.readText() && await clipboardService.hasResources()) {
+				return commandService.executeCommand(TerminalCommandId.Paste);
+			}
+			return commandService.executeCommand(TerminalCommandId.SendSequence, { text: ctrlV });
+		}
 	});
 }