diff --git a/extensions/git/package.json b/extensions/git/package.json
index 013d1375ea3..9e95f9a0c7c 100644
--- a/extensions/git/package.json
+++ b/extensions/git/package.json
@@ -2675,8 +2675,18 @@
           ]
         },
         "git.publishBeforeContinueOn": {
-          "type": "boolean",
-          "default": true,
+          "type": "string",
+          "enum": [
+            "prompt",
+            "always",
+            "never"
+          ],
+          "markdownEnumDescriptions": [
+            "%config.publishBeforeContinueOn.prompt%",
+            "%config.publishBeforeContinueOn.always%",
+            "%config.publishBeforeContinueOn.never%"
+          ],
+          "default": "prompt",
           "markdownDescription": "%config.publishBeforeContinueOn%",
           "scope": "resource",
           "tags": [
diff --git a/extensions/git/package.nls.json b/extensions/git/package.nls.json
index 24acb32bac3..3414836a971 100644
--- a/extensions/git/package.nls.json
+++ b/extensions/git/package.nls.json
@@ -243,6 +243,9 @@
 	"config.mergeEditor": "Open the merge editor for files that are currently under conflict.",
 	"config.optimisticUpdate": "Controls whether to optimistically update the state of the Source Control view after running git commands.",
 	"config.publishBeforeContinueOn": "Controls whether to publish unpublished git state when using Continue Working On from a git repository.",
+	"config.publishBeforeContinueOn.always": "Always publish unpublished git state when using Continue Working On from a git repository",
+	"config.publishBeforeContinueOn.never": "Never publish unpublished git state when using Continue Working On from a git repository",
+	"config.publishBeforeContinueOn.prompt": "Prompt to publish unpublished git state when using Continue Working On from a git repository",
 	"submenu.explorer": "Git",
 	"submenu.commit": "Commit",
 	"submenu.commit.amend": "Amend",
diff --git a/extensions/git/src/editSessionIdentityProvider.ts b/extensions/git/src/editSessionIdentityProvider.ts
index 69e3918407b..b66d1af2c3c 100644
--- a/extensions/git/src/editSessionIdentityProvider.ts
+++ b/extensions/git/src/editSessionIdentityProvider.ts
@@ -16,8 +16,9 @@ export class GitEditSessionIdentityProvider implements vscode.EditSessionIdentit
 		this.providerRegistration = vscode.workspace.registerEditSessionIdentityProvider('file', this);
 
 		vscode.workspace.onWillCreateEditSessionIdentity((e) => {
-			if (vscode.workspace.getConfiguration('git').get('publishBeforeContinueOn')) {
-				e.waitUntil(this._onWillCreateEditSessionIdentity(e.workspaceFolder, e.token));
+			const publishBeforeContinueOn = vscode.workspace.getConfiguration('git').get<'never' | 'always' | 'prompt'>('publishBeforeContinueOn', 'prompt');
+			if (publishBeforeContinueOn !== 'never') {
+				e.waitUntil(this._onWillCreateEditSessionIdentity(e.workspaceFolder, e.token, publishBeforeContinueOn));
 			}
 		});
 	}
@@ -66,12 +67,12 @@ export class GitEditSessionIdentityProvider implements vscode.EditSessionIdentit
 		}
 	}
 
-	private async _onWillCreateEditSessionIdentity(workspaceFolder: vscode.WorkspaceFolder, cancellationToken: vscode.CancellationToken): Promise<void> {
+	private async _onWillCreateEditSessionIdentity(workspaceFolder: vscode.WorkspaceFolder, cancellationToken: vscode.CancellationToken, publishBeforeContinueOn: 'always' | 'prompt'): Promise<void> {
 		const cancellationPromise = createCancellationPromise(cancellationToken);
-		await Promise.race([this._doPublish(workspaceFolder), cancellationPromise]);
+		await Promise.race([this._doPublish(workspaceFolder, publishBeforeContinueOn), cancellationPromise]);
 	}
 
-	private async _doPublish(workspaceFolder: vscode.WorkspaceFolder) {
+	private async _doPublish(workspaceFolder: vscode.WorkspaceFolder, publishBeforeContinueOn: 'always' | 'prompt') {
 		await this.model.openRepository(path.dirname(workspaceFolder.uri.fsPath));
 
 		const repository = this.model.getRepository(workspaceFolder.uri);
@@ -84,6 +85,26 @@ export class GitEditSessionIdentityProvider implements vscode.EditSessionIdentit
 		// If this branch hasn't been published to the remote yet,
 		// ensure that it is published before Continue On is invoked
 		if (!repository.HEAD?.upstream && repository.HEAD?.type === RefType.Head) {
+
+			if (publishBeforeContinueOn === 'prompt') {
+				const always = vscode.l10n.t('Always');
+				const never = vscode.l10n.t('Never');
+				const selection = await vscode.window.showInformationMessage(
+					vscode.l10n.t('The current branch is not published to the remote. Would you like to publish it to access your changes elsewhere?'),
+					{ modal: true },
+					...[always, never]
+				);
+				switch (selection) {
+					case always:
+						vscode.workspace.getConfiguration('git').update('publishBeforeContinueOn', 'always');
+						break;
+					case never:
+						vscode.workspace.getConfiguration('git').update('publishBeforeContinueOn', 'never');
+					default:
+						return;
+				}
+			}
+
 			await vscode.window.withProgress({
 				location: vscode.ProgressLocation.Notification,
 				title: vscode.l10n.t('Publishing branch...')