diff --git a/src/vs/workbench/browser/parts/editor/editorGroupView.ts b/src/vs/workbench/browser/parts/editor/editorGroupView.ts
index e0761b1f1db..faddd4e7b06 100644
--- a/src/vs/workbench/browser/parts/editor/editorGroupView.ts
+++ b/src/vs/workbench/browser/parts/editor/editorGroupView.ts
@@ -544,6 +544,9 @@ export class EditorGroupView extends Themable implements IEditorGroupView {
 
 		// Visibility
 		this._register(this.groupsView.onDidVisibilityChange(e => this.onDidVisibilityChange(e)));
+
+		// Focus
+		this._register(this.onDidFocus(() => this.onDidGainFocus()));
 	}
 
 	private onDidGroupModelChange(e: IGroupModelChangeEvent): void {
@@ -578,6 +581,9 @@ export class EditorGroupView extends Themable implements IEditorGroupView {
 			case GroupModelChangeKind.EDITOR_DIRTY:
 				this.onDidChangeEditorDirty(e.editor);
 				break;
+			case GroupModelChangeKind.EDITOR_TRANSIENT:
+				this.onDidChangeEditorTransient(e.editor);
+				break;
 			case GroupModelChangeKind.EDITOR_LABEL:
 				this.onDidChangeEditorLabel(e.editor);
 				break;
@@ -762,6 +768,17 @@ export class EditorGroupView extends Themable implements IEditorGroupView {
 		this.titleControl.updateEditorDirty(editor);
 	}
 
+	private onDidChangeEditorTransient(editor: EditorInput): void {
+		const transient = this.model.isTransient(editor);
+
+		// Transient state overrides the `enablePreview` setting,
+		// so when an editor leaves the transient state, we have
+		// to ensure its preview state is also cleared.
+		if (!transient && !this.groupsView.partOptions.enablePreview) {
+			this.pinEditor(editor);
+		}
+	}
+
 	private onDidChangeEditorLabel(editor: EditorInput): void {
 
 		// Forward to title control
@@ -774,6 +791,18 @@ export class EditorGroupView extends Themable implements IEditorGroupView {
 		this.editorPane.setVisible(visible);
 	}
 
+	private onDidGainFocus(): void {
+		if (this.activeEditor) {
+
+			// We aggressively clear the transient state of editors
+			// as soon as the group gains focus. This is to ensure
+			// that the transient state is not staying around when
+			// the user interacts with the editor.
+
+			this.setTransient(this.activeEditor, false);
+		}
+	}
+
 	//#endregion
 
 	//#region IEditorGroupView
diff --git a/src/vs/workbench/services/editor/test/browser/editorGroupsService.test.ts b/src/vs/workbench/services/editor/test/browser/editorGroupsService.test.ts
index e42c6116bc7..f1e25f4a355 100644
--- a/src/vs/workbench/services/editor/test/browser/editorGroupsService.test.ts
+++ b/src/vs/workbench/services/editor/test/browser/editorGroupsService.test.ts
@@ -1881,6 +1881,9 @@ suite('EditorGroupsService', () => {
 
 		await group.openEditor(input2, { transient: true });
 		assert.strictEqual(group.isPinned(input2), false);
+
+		group.setTransient(input2, false);
+		assert.strictEqual(group.isPinned(input2), true);
 	});
 
 	ensureNoDisposablesAreLeakedInTestSuite();
diff --git a/src/vs/workbench/services/history/browser/historyService.ts b/src/vs/workbench/services/history/browser/historyService.ts
index 3cef7fa9416..efaf3103c6c 100644
--- a/src/vs/workbench/services/history/browser/historyService.ts
+++ b/src/vs/workbench/services/history/browser/historyService.ts
@@ -35,6 +35,21 @@ import { ILifecycleService, LifecyclePhase } from 'vs/workbench/services/lifecyc
 import { ILogService, LogLevel } from 'vs/platform/log/common/log';
 import { mainWindow } from 'vs/base/browser/window';
 
+interface ISerializedEditorHistoryEntry {
+	readonly editor: Omit<IResourceEditorInput, 'resource'> & { resource: string };
+}
+
+interface IRecentlyClosedEditor {
+	readonly editorId: string | undefined;
+	readonly editor: IUntypedEditorInput;
+
+	readonly resource: URI | undefined;
+	readonly associatedResources: URI[];
+
+	readonly index: number;
+	readonly sticky: boolean;
+}
+
 export class HistoryService extends Disposable implements IHistoryService {
 
 	declare readonly _serviceBrand: undefined;
@@ -47,8 +62,6 @@ export class HistoryService extends Disposable implements IHistoryService {
 
 	private readonly editorHelper = this.instantiationService.createInstance(EditorHelper);
 
-
-
 	constructor(
 		@IEditorService private readonly editorService: EditorServiceImpl,
 		@IEditorGroupsService private readonly editorGroupService: IEditorGroupsService,
@@ -59,7 +72,8 @@ export class HistoryService extends Disposable implements IHistoryService {
 		@IWorkspacesService private readonly workspacesService: IWorkspacesService,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
 		@IWorkbenchLayoutService private readonly layoutService: IWorkbenchLayoutService,
-		@IContextKeyService private readonly contextKeyService: IContextKeyService
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@ILogService private readonly logService: ILogService
 	) {
 		super();
 
@@ -176,6 +190,8 @@ export class HistoryService extends Disposable implements IHistoryService {
 		// Handle editor change unless the editor is transient
 		if (!activeEditorPane?.group.isTransient(activeEditorPane.input)) {
 			this.handleActiveEditorChange(activeEditorGroup, activeEditorPane);
+		} else {
+			this.logService.trace(`[History]: ignoring transient editor change (editor: ${activeEditorPane.input?.resource?.toString()}})`);
 		}
 
 		// Listen to selection changes unless the editor is transient
@@ -183,6 +199,8 @@ export class HistoryService extends Disposable implements IHistoryService {
 			this.activeEditorListeners.add(activeEditorPane.onDidChangeSelection(e => {
 				if (!activeEditorPane.group.isTransient(activeEditorPane.input)) {
 					this.handleActiveEditorSelectionChangeEvent(activeEditorGroup, activeEditorPane, e);
+				} else {
+					this.logService.trace(`[History]: ignoring transient editor selection change (editor: ${activeEditorPane.input?.resource?.toString()}})`);
 				}
 			}));
 		}
@@ -2077,18 +2095,3 @@ class EditorHelper {
 		}
 	}
 }
-
-interface ISerializedEditorHistoryEntry {
-	editor: Omit<IResourceEditorInput, 'resource'> & { resource: string };
-}
-
-interface IRecentlyClosedEditor {
-	editorId: string | undefined;
-	editor: IUntypedEditorInput;
-
-	resource: URI | undefined;
-	associatedResources: URI[];
-
-	index: number;
-	sticky: boolean;
-}