diff --git a/news/2 Fixes/14730.md b/news/2 Fixes/14730.md
new file mode 100644
index 000000000000..1cc2782becc2
--- /dev/null
+++ b/news/2 Fixes/14730.md	
@@ -0,0 +1 @@
+Change drive first before changing directory in windows, to anticipate running file outside working directory with different storage drive. (thanks [afikrim](https://github.com/afikrim))
diff --git a/src/client/terminals/codeExecution/terminalCodeExecution.ts b/src/client/terminals/codeExecution/terminalCodeExecution.ts
index e3277ce18566..63c44be38ae9 100644
--- a/src/client/terminals/codeExecution/terminalCodeExecution.ts
+++ b/src/client/terminals/codeExecution/terminalCodeExecution.ts
@@ -92,6 +92,16 @@ export class TerminalCodeExecutionProvider implements ICodeExecutionService {
         }
         const fileDirPath = path.dirname(file.fsPath);
         if (fileDirPath.length > 0) {
+            if (this.platformService.isWindows && /[a-z]\:/i.test(fileDirPath)) {
+                const currentDrive =
+                    typeof this.workspace.rootPath === 'string'
+                        ? this.workspace.rootPath.replace(/\:.*/g, '')
+                        : undefined;
+                const fileDrive = fileDirPath.replace(/\:.*/g, '');
+                if (fileDrive !== currentDrive) {
+                    await this.getTerminalService(file).sendText(`${fileDrive}:`);
+                }
+            }
             await this.getTerminalService(file).sendText(`cd ${fileDirPath.fileToCommandArgument()}`);
         }
     }
diff --git a/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts b/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts
index 1bdfd90253fe..7644b592a249 100644
--- a/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts
+++ b/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts
@@ -163,6 +163,40 @@ suite('Terminal - Code Execution', () => {
                     .returns(() => terminalService.object);
             });
 
+            async function ensureWeSetCurrentDriveBeforeChangingDirectory(_isWindows: boolean): Promise<void> {
+                const file = Uri.file(path.join('d:', 'path', 'to', 'file', 'one.py'));
+                terminalSettings.setup((t) => t.executeInFileDir).returns(() => true);
+                workspace.setup((w) => w.rootPath).returns(() => path.join('c:', 'path', 'to'));
+                workspaceFolder.setup((w) => w.uri).returns(() => Uri.file(path.join('c:', 'path', 'to')));
+                platform.setup((p) => p.isWindows).returns(() => true);
+                settings.setup((s) => s.pythonPath).returns(() => PYTHON_PATH);
+                terminalSettings.setup((t) => t.launchArgs).returns(() => []);
+
+                await executor.executeFile(file);
+                terminalService.verify(async (t) => t.sendText(TypeMoq.It.isValue('d:')), TypeMoq.Times.once());
+            }
+            test('Ensure we set current drive before changing directory on windows', async () => {
+                await ensureWeSetCurrentDriveBeforeChangingDirectory(true);
+            });
+
+            async function ensureWeDoNotChangeDriveIfDriveLetterSameAsFileDriveLetter(
+                _isWindows: boolean,
+            ): Promise<void> {
+                const file = Uri.file(path.join('c:', 'path', 'to', 'file', 'one.py'));
+                terminalSettings.setup((t) => t.executeInFileDir).returns(() => true);
+                workspace.setup((w) => w.rootPath).returns(() => path.join('c:', 'path', 'to'));
+                workspaceFolder.setup((w) => w.uri).returns(() => Uri.file(path.join('c:', 'path', 'to')));
+                platform.setup((p) => p.isWindows).returns(() => true);
+                settings.setup((s) => s.pythonPath).returns(() => PYTHON_PATH);
+                terminalSettings.setup((t) => t.launchArgs).returns(() => []);
+
+                await executor.executeFile(file);
+                terminalService.verify(async (t) => t.sendText(TypeMoq.It.isValue('c:')), TypeMoq.Times.never());
+            }
+            test('Ensure we do not change drive if current drive letter is same as the file drive letter on windows', async () => {
+                await ensureWeDoNotChangeDriveIfDriveLetterSameAsFileDriveLetter(true);
+            });
+
             async function ensureWeSetCurrentDirectoryBeforeExecutingAFile(_isWindows: boolean): Promise<void> {
                 const file = Uri.file(path.join('c', 'path', 'to', 'file', 'one.py'));
                 terminalSettings.setup((t) => t.executeInFileDir).returns(() => true);