diff --git a/src/client/terminals/codeExecution/terminalCodeExecution.ts b/src/client/terminals/codeExecution/terminalCodeExecution.ts
index ea444af4d89e..e7ed3bf7f61d 100644
--- a/src/client/terminals/codeExecution/terminalCodeExecution.ts
+++ b/src/client/terminals/codeExecution/terminalCodeExecution.ts
@@ -38,12 +38,15 @@ export class TerminalCodeExecutionProvider implements ICodeExecutionService {
     ) {}
 
     public async executeFile(file: Uri, options?: { newTerminalPerFile: boolean }) {
-        await this.setCwdForFileExecution(file, options);
+        // If we're currently in a REPL, force creation of a new terminal for file execution
+        const finalOptions = await this.shouldForceNewTerminalForFileExecution(options);
+        
+        await this.setCwdForFileExecution(file, finalOptions);
         const { command, args } = await this.getExecuteFileArgs(file, [
             file.fsPath.fileToCommandArgumentForPythonExt(),
         ]);
 
-        await this.getTerminalService(file, options).sendCommand(command, args);
+        await this.getTerminalService(file, finalOptions).sendCommand(command, args);
     }
 
     public async execute(code: string, resource?: Uri): Promise<void> {
@@ -124,6 +127,28 @@ export class TerminalCodeExecutionProvider implements ICodeExecutionService {
     public async getExecuteFileArgs(resource?: Uri, executeArgs: string[] = []): Promise<PythonExecInfo> {
         return this.getExecutableInfo(resource, executeArgs);
     }
+
+    /**
+     * Check if we should force creation of a new terminal for file execution.
+     * This is needed when the current terminal is in Python REPL mode to avoid
+     * sending the file execution command to the Python interpreter instead of the shell.
+     */
+    private async shouldForceNewTerminalForFileExecution(
+        options?: { newTerminalPerFile: boolean }
+    ): Promise<{ newTerminalPerFile: boolean }> {
+        // If already set to create new terminal, respect that
+        if (options?.newTerminalPerFile) {
+            return { newTerminalPerFile: true };
+        }
+
+        // If we have an active REPL, force creation of a new terminal
+        if (this.replActive && (await this.replActive)) {
+            return { newTerminalPerFile: true };
+        }
+
+        // Otherwise, use original options or default to false
+        return options || { newTerminalPerFile: false };
+    }
     private getTerminalService(resource: Resource, options?: { newTerminalPerFile: boolean }): ITerminalService {
         return this.terminalServiceFactory.getTerminalService({
             resource,
diff --git a/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts b/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts
index b5bcecd971ea..0eda12ce5b3f 100644
--- a/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts
+++ b/src/test/terminals/codeExecution/terminalCodeExec.unit.test.ts
@@ -649,6 +649,43 @@ suite('Terminal - Code Execution', () => {
                 terminalService.verify(async (t) => t.executeCommand('cmd2', true), TypeMoq.Times.once());
             });
 
+            test('Ensure new terminal is created when REPL is active and executeFile is called', async () => {
+                // Setup a file to execute
+                const file = Uri.file(path.join('c:', 'path', 'to', 'file', 'test.py'));
+                
+                // Setup mocks for interpreter and settings
+                const pythonPath = 'usr/bin/python1234';
+                const terminalArgs = ['-a', 'b', 'c'];
+                platform.setup((p) => p.isWindows).returns(() => false);
+                interpreterService
+                    .setup((s) => s.getActiveInterpreter(TypeMoq.It.isAny()))
+                    .returns(() => Promise.resolve(({ path: pythonPath } as unknown) as PythonEnvironment));
+                terminalSettings.setup((t) => t.launchArgs).returns(() => terminalArgs);
+                terminalSettings.setup((t) => t.executeInFileDir).returns(() => false);
+
+                // First, initialize REPL to make replActive = true
+                await executor.initializeRepl(file);
+                
+                // Reset terminal factory to track calls for file execution
+                terminalFactory.reset();
+                terminalFactory
+                    .setup((f) => f.getTerminalService(TypeMoq.It.isAny()))
+                    .callback((options: TerminalCreationOptions & { newTerminalPerFile?: boolean }) => {
+                        // When REPL is active, executeFile should force newTerminalPerFile = true
+                        assert.equal(options.newTerminalPerFile, true, 'Should force new terminal when REPL is active');
+                    })
+                    .returns(() => terminalService.object);
+
+                // Execute file - this should force creation of a new terminal
+                await executor.executeFile(file);
+
+                // Verify that getTerminalService was called with newTerminalPerFile: true
+                terminalFactory.verify(
+                    (f) => f.getTerminalService(TypeMoq.It.isAny()),
+                    TypeMoq.Times.once()
+                );
+            });
+
             test('Ensure code is sent to the same terminal for a particular resource', async () => {
                 const resource = Uri.file('a');
                 terminalFactory.reset();