diff --git a/packages/core/src/browser/common-frontend-contribution.ts b/packages/core/src/browser/common-frontend-contribution.ts
index f436fcf2349b4..9a94250432617 100644
--- a/packages/core/src/browser/common-frontend-contribution.ts
+++ b/packages/core/src/browser/common-frontend-contribution.ts
@@ -57,7 +57,7 @@ import { QuickInputService, QuickPickItem, QuickPickItemOrSeparator, QuickPickSe
 import { AsyncLocalizationProvider } from '../common/i18n/localization';
 import { nls } from '../common/nls';
 import { CurrentWidgetCommandAdapter } from './shell/current-widget-command-adapter';
-import { ConfirmDialog, confirmExitWithOrWithoutSaving, Dialog } from './dialogs';
+import { ConfirmDialog, confirmExitWithOrWithoutSaving, confirmExitWithOrWithoutSavingResult, Dialog } from './dialogs';
 import { WindowService } from './window/window-service';
 import { FrontendApplicationConfigProvider } from './frontend-application-config-provider';
 import { DecorationStyle } from './decoration-style';
@@ -1200,17 +1200,16 @@ export class CommonFrontendContribution implements FrontendApplicationContributi
                 action: async () => {
                     const captionsToSave = this.unsavedTabsCaptions();
                     const untitledCaptionsToSave = this.unsavedUntitledTabsCaptions();
-                    const result = await confirmExitWithOrWithoutSaving(captionsToSave, async () => {
+                    const shouldExit = await confirmExitWithOrWithoutSaving(captionsToSave, async () => {
                         await this.saveDirty(untitledCaptionsToSave);
                         await this.shell.saveAll();
                     });
-                    if (this.shell.canSaveAll()) {
-                        this.shouldPreventClose = true;
-                        return false;
-                    } else {
-                        this.shouldPreventClose = false;
-                        return result;
-                    }
+                    const allSavedOrDoNotSave = (
+                        confirmExitWithOrWithoutSavingResult.save === shouldExit && untitledCaptionsToSave.length === 0 // cancel if any captions failed to save
+                    ) || confirmExitWithOrWithoutSavingResult.doNotSave === shouldExit;
+
+                    this.shouldPreventClose = !allSavedOrDoNotSave;
+                    return allSavedOrDoNotSave;
 
                 }
             };
@@ -1236,11 +1235,19 @@ export class CommonFrontendContribution implements FrontendApplicationContributi
             this.windowService.reload();
         }
     }
+    /**
+     * saves any dirty widget in toSave
+     * side effect - will pop all widgets from toSave that was saved
+     * @param toSave
+     */
     protected async saveDirty(toSave: Widget[]): Promise<void> {
         for (const widget of toSave) {
             const saveable = Saveable.get(widget);
             if (saveable?.dirty) {
                 await this.saveResourceService.save(widget);
+                if (!this.saveResourceService.canSave(widget)) {
+                    toSave.pop();
+                }
             }
         }
     }
diff --git a/packages/core/src/browser/dialogs.ts b/packages/core/src/browser/dialogs.ts
index 2ab0a1203e976..11493b7e59a5f 100644
--- a/packages/core/src/browser/dialogs.ts
+++ b/packages/core/src/browser/dialogs.ts
@@ -458,11 +458,18 @@ export class ConfirmSaveDialog extends AbstractDialog<boolean | undefined> {
 
 }
 
+export enum confirmExitWithOrWithoutSavingResult {
+    save = 'save',
+    doNotSave = 'doNotSave',
+    cancel = 'cancel',
+}
+
 // Asks the user to confirm whether they want to exit with or without saving the changes
-export async function confirmExitWithOrWithoutSaving(captionsToSave: string[], performSave: () => Promise<void>): Promise<boolean> {
+export async function confirmExitWithOrWithoutSaving(captionsToSave: string[], performSave?: () => Promise<void>): Promise<confirmExitWithOrWithoutSavingResult> {
     const div: HTMLElement = document.createElement('div');
     div.innerText = nls.localizeByDefault("Your changes will be lost if you don't save them.");
 
+    let result;
     if (captionsToSave.length > 0) {
         const span = document.createElement('span');
         span.appendChild(document.createElement('br'));
@@ -474,7 +481,7 @@ export async function confirmExitWithOrWithoutSaving(captionsToSave: string[], p
         });
         span.appendChild(document.createElement('br'));
         div.appendChild(span);
-        const result = await new ConfirmSaveDialog({
+        result = await new ConfirmSaveDialog({
             title: nls.localizeByDefault('Do you want to save the changes to the following {0} files?', captionsToSave.length),
             msg: div,
             dontSave: nls.localizeByDefault("Don't Save"),
@@ -482,14 +489,18 @@ export async function confirmExitWithOrWithoutSaving(captionsToSave: string[], p
             cancel: Dialog.CANCEL
         }).open();
 
-        if (result) {
+        if (result && performSave) {
             await performSave();
         }
-        return result !== undefined;
     } else {
         // fallback if not passed with an empty caption-list.
-        return confirmExit();
+        result = confirmExit();
     }
+    if (result !== undefined) {
+        return result === true ? confirmExitWithOrWithoutSavingResult.save : confirmExitWithOrWithoutSavingResult.doNotSave;
+    } else {
+        return confirmExitWithOrWithoutSavingResult.cancel;
+    };
 
 }
 @injectable()