diff --git a/package.json b/package.json
index 5d49d8210d3..c8b077638e5 100644
--- a/package.json
+++ b/package.json
@@ -144,11 +144,6 @@
                 "key": "alt+enter",
                 "when": "editorTextFocus && !editorHasSelection && jupyter.hascodecells && !notebookEditorFocused"
             },
-            {
-                "key": "shift+enter",
-                "when": "activeEditor == 'workbench.editor.interactive' && notebookKernel =~ /^ms-toolsai.jupyter\\// || activeEditor == 'workbench.editor.interactive' && !notebookKernel",
-                "command": "interactive.execute"
-            },
             {
                 "key": "escape",
                 "when": "activeEditor == 'workbench.editor.interactive' && !editorHoverVisible && !suggestWidgetVisible && !isComposing && !inSnippetMode && !exceptionWidgetVisible && !selectionAnchorSet && !LinkedEditingInputVisible && !renameInputVisible && !editorHasSelection && !accessibilityHelpWidgetVisible && !breakpointWidgetVisible && !findWidgetVisible && !markersNavigationVisible && !parameterHintsVisible && !editorHasMultipleSelections && !notificationToastsVisible",
diff --git a/src/interactive-window/interactiveWindowProvider.ts b/src/interactive-window/interactiveWindowProvider.ts
index 2bd5966b740..313b688d0da 100644
--- a/src/interactive-window/interactiveWindowProvider.ts
+++ b/src/interactive-window/interactiveWindowProvider.ts
@@ -121,6 +121,10 @@ export class InteractiveWindowProvider implements IInteractiveWindowProvider, IE
                 tab,
                 Uri.parse(iw.inputBoxUriString)
             );
+
+            this.updateExecuteConfigSetting().catch((ex) =>
+                logger.warn('Failed to update executeWithShiftEnter setting', ex)
+            );
             result.notifyConnectionReset();
 
             this._windows.push(result);
@@ -166,10 +170,36 @@ export class InteractiveWindowProvider implements IInteractiveWindowProvider, IE
         }
 
         await result.ensureInitialized();
+        this.updateExecuteConfigSetting().catch((ex) =>
+            logger.warn('Failed to update executeWithShiftEnter setting', ex)
+        );
 
         return result;
     }
 
+    private async updateExecuteConfigSetting() {
+        const updatedExecuteConfigKey = 'updatedExecuteInteractiveConfig';
+        const updatedExecuteConfig = this.globalMemento.get<boolean>(updatedExecuteConfigKey);
+        if (updatedExecuteConfig) {
+            // We've already updated the setting, don't change it again if the user removed it
+            return;
+        }
+
+        const config = workspace.getConfiguration('interactiveWindow');
+        const inspected = config.inspect<boolean>('executeWithShiftEnter');
+
+        if (
+            inspected?.workspaceValue === undefined &&
+            inspected?.workspaceFolderValue === undefined &&
+            inspected?.globalValue === undefined
+        ) {
+            // Update the setting to execute with shift+enter if the user has not set it explicitly
+            // This is to ensure that the behavior stays consistent, but we should only keep doing this for a single release cycle
+            await config.update('executeWithShiftEnter', true, ConfigurationTarget.Global);
+            await this.globalMemento.update(updatedExecuteConfigKey, undefined);
+        }
+    }
+
     /**
      * Given a text document, return the associated interactive window if one exists.
      * @param owner The URI of a text document which may be associated with an interactive window.