diff --git a/src/vs/vscode.d.ts b/src/vs/vscode.d.ts
index 125efd8243e8dd4d7e23d4915c88f2ca3e609e9f..922be1f300d999740e20c4764cb7e5a0109c6dd5 100644
--- a/src/vs/vscode.d.ts
+++ b/src/vs/vscode.d.ts
@@ -7744,7 +7744,7 @@ declare module 'vscode' {
 		 * your extension should first check to see if any backups exist for the resource. If there is a backup, your
 		 * extension should load the file contents from there instead of from the resource in the workspace.
 		 *
-		 * `backup` is triggered approximately one second after the the user stops editing the document. If the user
+		 * `backup` is triggered approximately one second after the user stops editing the document. If the user
 		 * rapidly edits the document, `backup` will not be invoked until the editing stops.
 		 *
 		 * `backup` is not invoked when `auto save` is enabled (since auto save already persists the resource).
diff --git a/src/vs/workbench/api/browser/viewsExtensionPoint.ts b/src/vs/workbench/api/browser/viewsExtensionPoint.ts
index 6be78f4ec8954ae80d0d73231857ea7dcf22441e..b785735c5a6d3d38f91512fdb0c54c873c8aa2e5 100644
--- a/src/vs/workbench/api/browser/viewsExtensionPoint.ts
+++ b/src/vs/workbench/api/browser/viewsExtensionPoint.ts
@@ -110,7 +110,7 @@ const viewDescriptor: IJSONSchema = {
 	defaultSnippets: [{ body: { id: '${1:id}', name: '${2:name}' } }],
 	properties: {
 		type: {
-			markdownDescription: localize('vscode.extension.contributes.view.type', "Type of the the view. This can either be `tree` for a tree view based view or `webview` for a webview based view. The default is `tree`."),
+			markdownDescription: localize('vscode.extension.contributes.view.type', "Type of the view. This can either be `tree` for a tree view based view or `webview` for a webview based view. The default is `tree`."),
 			type: 'string',
 			enum: [
 				'tree',
diff --git a/src/vs/workbench/api/common/extHostCommands.ts b/src/vs/workbench/api/common/extHostCommands.ts
index 228d60c37fc8c2644db1e7f75e7de0faf628ebc6..9c29d1f66c2dcfbc318c40769a9bd64a7b5e9450 100644
--- a/src/vs/workbench/api/common/extHostCommands.ts
+++ b/src/vs/workbench/api/common/extHostCommands.ts
@@ -103,7 +103,7 @@ export class ExtHostCommands implements ExtHostCommandsShape {
 
 			const internalArgs = apiCommand.args.map((arg, i) => {
 				if (!arg.validate(apiArgs[i])) {
-					throw new Error(`Invalid argument '${arg.name}' when running '${apiCommand.id}', receieved: ${apiArgs[i]}`);
+					throw new Error(`Invalid argument '${arg.name}' when running '${apiCommand.id}', received: ${apiArgs[i]}`);
 				}
 				return arg.convert(apiArgs[i]);
 			});
diff --git a/src/vs/workbench/browser/parts/editor/media/tabstitlecontrol.css b/src/vs/workbench/browser/parts/editor/media/tabstitlecontrol.css
index 65e31e2fd9f3372393ec0bd9684d55c305447c34..9ec69667ecd9afdaed83d8c9bf1f950ae98652cb 100644
--- a/src/vs/workbench/browser/parts/editor/media/tabstitlecontrol.css
+++ b/src/vs/workbench/browser/parts/editor/media/tabstitlecontrol.css
@@ -38,10 +38,7 @@
 
 .monaco-workbench .part.editor > .content .editor-group-container > .title.tabs > .tabs-and-actions-container {
 	display: flex;
-}
-
-.monaco-workbench .part.editor > .content .editor-group-container > .title.tabs > .tabs-and-actions-container.tabs-border-bottom {
-	position: relative;
+	position: relative; /* position tabs border bottom or editor actions (when tabs wrap) relative to this container */
 }
 
 .monaco-workbench .part.editor > .content .editor-group-container > .title.tabs > .tabs-and-actions-container.tabs-border-bottom::after {
@@ -77,6 +74,13 @@
 	overflow: scroll !important;
 }
 
+.monaco-workbench .part.editor > .content .editor-group-container > .title > .tabs-and-actions-container.wrapping .tabs-container {
+
+	/* Enable wrapping via flex layout and dynamic height */
+	height: auto;
+	flex-wrap: wrap;
+}
+
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container::-webkit-scrollbar {
 	display: none; /* Chrome + Safari: hide scrollbar */
 }
@@ -93,6 +97,10 @@
 	padding-left: 10px;
 }
 
+.monaco-workbench .part.editor > .content .editor-group-container > .title > .tabs-and-actions-container.wrapping .tabs-container > .tab:last-child {
+	margin-right: var(--last-tab-margin-right); /* when tabs wrap, we need a margin away from the absolute positioned editor actions */
+}
+
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.sizing-shrink.has-icon.tab-actions-right,
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.sizing-shrink.has-icon.tab-actions-off:not(.sticky-compact) {
 	padding-left: 5px; /* reduce padding when we show icons and are in shrinking mode and tab actions is not left (unless sticky-compact) */
@@ -105,6 +113,10 @@
 	flex-shrink: 0;
 }
 
+.monaco-workbench .part.editor > .content .editor-group-container > .title > .tabs-and-actions-container.wrapping .tabs-container > .tab.sizing-fit {
+	flex-grow: 1; /* grow the tabs to fill each row for a more homogeneous look when tabs wrap */
+}
+
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.sizing-shrink {
 	min-width: 80px;
 	flex-basis: 0; /* all tabs are even */
@@ -149,9 +161,7 @@
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container.disable-sticky-tabs > .tab.sizing-shrink.sticky-compact,
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container.disable-sticky-tabs > .tab.sizing-fit.sticky-shrink,
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container.disable-sticky-tabs > .tab.sizing-shrink.sticky-shrink {
-
-	/** Disable sticky positions for sticky compact/shrink tabs if the available space is too little */
-	position: static;
+	position: static; /** disable sticky positions for sticky compact/shrink tabs if the available space is too little */
 }
 
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.tab-actions-left .action-label {
@@ -163,7 +173,7 @@
 	content: '';
 	display: flex;
 	flex: 0;
-	width: 5px; /* Reserve space to hide tab fade when close button is left or off (fixes https://github.com/microsoft/vscode/issues/45728) */
+	width: 5px; /* reserve space to hide tab fade when close button is left or off (fixes https://github.com/microsoft/vscode/issues/45728) */
 }
 
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.sizing-shrink.tab-actions-left {
@@ -276,7 +286,7 @@
 
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.tab-actions-right.sizing-shrink > .tab-actions {
 	flex: 0;
-	overflow: hidden; /* let the tab actions be pushed out of view when sizing is set to shrink to make more room... */
+	overflow: hidden; /* let the tab actions be pushed out of view when sizing is set to shrink to make more room */
 }
 
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.dirty.tab-actions-right.sizing-shrink > .tab-actions,
@@ -366,6 +376,14 @@
 	height: 35px;
 }
 
+.monaco-workbench .part.editor > .content .editor-group-container > .title > .tabs-and-actions-container.wrapping .editor-actions {
+
+	/* When tabs are wrapped, position the editor actions at the end of the very last row */
+	position: absolute;
+	bottom: 0;
+	right: 0;
+}
+
 /* Breadcrumbs */
 
 .monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-breadcrumbs .breadcrumbs-control {
diff --git a/src/vs/workbench/browser/parts/editor/tabsTitleControl.ts b/src/vs/workbench/browser/parts/editor/tabsTitleControl.ts
index 74056984c5203b7f15e94a27da89ebbc1b4e047a..d7cfb96a4883698943ba4c087d8942595e6a6396 100644
--- a/src/vs/workbench/browser/parts/editor/tabsTitleControl.ts
+++ b/src/vs/workbench/browser/parts/editor/tabsTitleControl.ts
@@ -91,7 +91,7 @@ export class TabsTitleControl extends TitleControl {
 	private tabActionBars: ActionBar[] = [];
 	private tabDisposables: IDisposable[] = [];
 
-	private dimensions: ITitleControlDimensions = {
+	private dimensions: ITitleControlDimensions & { used?: Dimension } = {
 		container: Dimension.None,
 		available: Dimension.None
 	};
@@ -571,6 +571,7 @@ export class TabsTitleControl extends TitleControl {
 			oldOptions.showIcons !== newOptions.showIcons ||
 			oldOptions.hasIcons !== newOptions.hasIcons ||
 			oldOptions.highlightModifiedTabs !== newOptions.highlightModifiedTabs ||
+			oldOptions.wrapTabs !== newOptions.wrapTabs ||
 			!equals(oldOptions.decorations, newOptions.decorations)
 		) {
 			this.redraw();
@@ -1274,19 +1275,30 @@ export class TabsTitleControl extends TitleControl {
 	}
 
 	getDimensions(): IEditorGroupTitleDimensions {
-		let height = TabsTitleControl.TAB_HEIGHT;
+		let height: number;
+
+		// Wrap: we need to ask `offsetHeight` to get
+		// the real height of the title area with wrapping.
+		if (this.accessor.partOptions.wrapTabs && this.tabsAndActionsContainer?.classList.contains('wrapping')) {
+			height = this.tabsAndActionsContainer.offsetHeight;
+		} else {
+			height = TabsTitleControl.TAB_HEIGHT;
+		}
+
+		const offset = height;
+
+		// Account for breadcrumbs if visible
 		if (this.breadcrumbsControl && !this.breadcrumbsControl.isHidden()) {
 			height += BreadcrumbsControl.HEIGHT; // Account for breadcrumbs if visible
 		}
 
-		return {
-			height,
-			offset: TabsTitleControl.TAB_HEIGHT
-		};
+		return { height, offset };
 	}
 
 	layout(dimensions: ITitleControlDimensions): Dimension {
-		this.dimensions = dimensions;
+
+		// Remember dimensions that we get
+		Object.assign(this.dimensions, dimensions);
 
 		// The layout of tabs can be an expensive operation because we access DOM properties
 		// that can result in the browser doing a full page layout to validate them. To buffer
@@ -1303,17 +1315,33 @@ export class TabsTitleControl extends TitleControl {
 	}
 
 	private doLayout(dimensions: ITitleControlDimensions): void {
+
+		// Only layout if we have valid tab index and dimensions
 		const activeTabAndIndex = this.group.activeEditor ? this.getTabAndIndex(this.group.activeEditor) : undefined;
-		if (!activeTabAndIndex || dimensions.container === Dimension.None || dimensions.available === Dimension.None) {
-			return; // nothing to do if not editor opened or we got no dimensions yet
+		if (activeTabAndIndex && dimensions.container !== Dimension.None && dimensions.available !== Dimension.None) {
+
+			// Breadcrumbs
+			this.doLayoutBreadcrumbs(dimensions);
+
+			// Tabs
+			const [activeTab, activeIndex] = activeTabAndIndex;
+			this.doLayoutTabs(activeTab, activeIndex, dimensions);
 		}
 
-		// Breadcrumbs
-		this.doLayoutBreadcrumbs(dimensions);
+		// Compute new dimension of tabs title control and remember it for future usages
+		const oldDimension = this.dimensions.used;
+		const newDimension = this.dimensions.used = new Dimension(dimensions.container.width, this.getDimensions().height);
 
-		// Tabs
-		const [activeTab, activeIndex] = activeTabAndIndex;
-		this.doLayoutTabs(activeTab, activeIndex);
+		// In case the height of the title control changed from before
+		// (currently only possible if tabs are set to wrap), we need
+		// to signal this to the outside via a `relayout` call so that
+		// e.g. the editor control can be adjusted accordingly.
+		if (
+			this.accessor.partOptions.wrapTabs &&
+			oldDimension && oldDimension.height !== newDimension.height
+		) {
+			this.group.relayout();
+		}
 	}
 
 	private doLayoutBreadcrumbs(dimensions: ITitleControlDimensions): void {
@@ -1322,8 +1350,8 @@ export class TabsTitleControl extends TitleControl {
 		}
 	}
 
-	private doLayoutTabs(activeTab: HTMLElement, activeIndex: number): void {
-		const [tabsContainer, tabsScrollbar] = assertAllDefined(this.tabsContainer, this.tabsScrollbar);
+	private doLayoutTabs(activeTab: HTMLElement, activeIndex: number, dimensions: ITitleControlDimensions): void {
+		const [tabsAndActionsContainer, tabsContainer, tabsScrollbar, editorToolbarContainer] = assertAllDefined(this.tabsAndActionsContainer, this.tabsContainer, this.tabsScrollbar, this.editorToolbarContainer);
 
 		//
 		// Synopsis
@@ -1381,6 +1409,55 @@ export class TabsTitleControl extends TitleControl {
 			tabsContainer.classList.remove('disable-sticky-tabs');
 		}
 
+		// Handle wrapping tabs according to setting:
+		// - enabled: only add class if tabs wrap and don't exceed available height
+		// - disabled: remove class
+		if (this.accessor.partOptions.wrapTabs) {
+			let tabsWrapMultiLine = tabsAndActionsContainer.classList.contains('wrapping');
+			let updateScrollbar = false;
+
+			// Tabs do not wrap multiline: add wrapping if tabs exceed the tabs container width
+			// and the height of the tabs container does not exceed the maximum
+			if (!tabsWrapMultiLine && allTabsWidth > visibleTabsContainerWidth) {
+				tabsAndActionsContainer.classList.add('wrapping');
+				tabsWrapMultiLine = true;
+			}
+
+			// Tabs wrap multiline: remove wrapping if height exceeds available height
+			// or the maximum allowed height
+			if (tabsWrapMultiLine && tabsContainer.offsetHeight > dimensions.available.height) {
+				tabsAndActionsContainer.classList.remove('wrapping');
+				tabsWrapMultiLine = false;
+				updateScrollbar = true;
+			}
+
+			// If we do not exceed the tabs container width, we cannot simply remove
+			// the wrap class because by wrapping tabs, they reduce their size
+			// and we would otherwise constantly add and remove the class. As such
+			// we need to check if the height of the tabs container is back to normal
+			// and then remove the wrap class.
+			if (tabsWrapMultiLine && allTabsWidth === visibleTabsContainerWidth && tabsContainer.offsetHeight === TabsTitleControl.TAB_HEIGHT) {
+				tabsAndActionsContainer.classList.remove('wrapping');
+				tabsWrapMultiLine = false;
+				updateScrollbar = true;
+			}
+
+			// Update `last-tab-margin-right` CSS variable to account for the absolute
+			// positioned editor actions container when tabs wrap. The margin needs to
+			// be the width of the editor actions container to avoid screen cheese.
+			tabsContainer.style.setProperty('--last-tab-margin-right', tabsWrapMultiLine ? `${editorToolbarContainer.offsetWidth}px` : '0');
+
+			// When tabs change from wrapping back to normal, we need to indicate this
+			// to the scrollbar so that revealing the active tab functions properly.
+			if (updateScrollbar) {
+				tabsScrollbar.setScrollPosition({
+					scrollLeft: tabsContainer.scrollLeft
+				});
+			}
+		} else {
+			tabsAndActionsContainer.classList.remove('wrapping');
+		}
+
 		let activeTabPosX: number | undefined;
 		let activeTabWidth: number | undefined;
 
@@ -1567,11 +1644,23 @@ registerThemingParticipant((theme: IColorTheme, collector: ICssStyleCollector) =
 	// Add border between tabs and breadcrumbs in high contrast mode.
 	if (theme.type === ColorScheme.HIGH_CONTRAST) {
 		const borderColor = (theme.getColor(TAB_BORDER) || theme.getColor(contrastBorder));
+		if (borderColor) {
+			collector.addRule(`
+				.monaco-workbench .part.editor > .content .editor-group-container > .title > .tabs-and-actions-container {
+					border-bottom: 1px solid ${borderColor};
+				}
+			`);
+		}
+	}
+
+	// Add bottom border to tabs when wrapping
+	const borderColor = theme.getColor(TAB_BORDER);
+	if (borderColor) {
 		collector.addRule(`
-			.monaco-workbench .part.editor > .content .editor-group-container > .title.tabs > .tabs-and-actions-container {
-				border-bottom: 1px solid ${borderColor};
-			}
-		`);
+				.monaco-workbench .part.editor > .content .editor-group-container > .title > .tabs-and-actions-container.wrapping .tabs-container > .tab {
+					border-bottom: 1px solid ${borderColor};
+				}
+			`);
 	}
 
 	// Styling with Outline color (e.g. high contrast theme)
diff --git a/src/vs/workbench/browser/workbench.contribution.ts b/src/vs/workbench/browser/workbench.contribution.ts
index 270463eed9440e03026510ec9246fc460bed09ff..b47ccfbe06afb3034b7565b75b8b40fb8e5e5f85 100644
--- a/src/vs/workbench/browser/workbench.contribution.ts
+++ b/src/vs/workbench/browser/workbench.contribution.ts
@@ -33,6 +33,11 @@ import { isStandalone } from 'vs/base/browser/browser';
 				'description': nls.localize('showEditorTabs', "Controls whether opened editors should show in tabs or not."),
 				'default': true
 			},
+			'workbench.editor.wrapTabs': {
+				'type': 'boolean',
+				'description': nls.localize('wrapTabs', "Controls whether tabs should be wrapped over multiple lines when exceeding available space or wether a scrollbar should appear instead."),
+				'default': false
+			},
 			'workbench.editor.scrollToSwitchTabs': {
 				'type': 'boolean',
 				'markdownDescription': nls.localize({ comment: ['This is the description for a setting. Values surrounded by single quotes are not to be translated.'], key: 'scrollToSwitchTabs' }, "Controls whether scrolling over tabs will open them or not. By default tabs will only reveal upon scrolling, but not open. You can press and hold the Shift-key while scrolling to change this behaviour for that duration. This value is ignored when `#workbench.editor.showTabs#` is disabled."),
diff --git a/src/vs/workbench/common/editor.ts b/src/vs/workbench/common/editor.ts
index db82863b0a679a1d1977dfe0b83a107a74f57997..99bde65fbb8e1105761a9f7ed0e5e6ff857f0e3a 100644
--- a/src/vs/workbench/common/editor.ts
+++ b/src/vs/workbench/common/editor.ts
@@ -1265,6 +1265,7 @@ export interface IWorkbenchEditorConfiguration {
 
 interface IEditorPartConfiguration {
 	showTabs?: boolean;
+	wrapTabs?: boolean;
 	scrollToSwitchTabs?: boolean;
 	highlightModifiedTabs?: boolean;
 	tabCloseButton?: 'left' | 'right' | 'off';
diff --git a/src/vs/workbench/contrib/debug/browser/replViewer.ts b/src/vs/workbench/contrib/debug/browser/replViewer.ts
index 5f6dbc2a786baaf8764c2e431d09059bcece8179..32e3dcb054353bc26e6104560ec3c04dce8aedc5 100644
--- a/src/vs/workbench/contrib/debug/browser/replViewer.ts
+++ b/src/vs/workbench/contrib/debug/browser/replViewer.ts
@@ -389,7 +389,7 @@ export class ReplAccessibilityProvider implements IListAccessibilityProvider<IRe
 			return localize('replVariableAriaLabel', "Variable {0}, value {1}", element.name, element.value);
 		}
 		if (element instanceof SimpleReplElement || element instanceof ReplEvaluationInput || element instanceof ReplEvaluationResult) {
-			return element.value + (element instanceof SimpleReplElement && element.count > 1 ? localize({ key: 'occurred', comment: ['Front will the the value of the debug console element. Placeholder will be replaced by a number which represents occurrance count.'] },
+			return element.value + (element instanceof SimpleReplElement && element.count > 1 ? localize({ key: 'occurred', comment: ['Front will the value of the debug console element. Placeholder will be replaced by a number which represents occurrance count.'] },
 				", occured {0} times", element.count) : '');
 		}
 		if (element instanceof RawObjectReplElement) {
diff --git a/src/vs/workbench/contrib/debug/common/replModel.ts b/src/vs/workbench/contrib/debug/common/replModel.ts
index f10608a01564d1f8be7134dbefb147b7ed227bef..f3e276042246d0ff6db9436ecee2b16acd6ebd5e 100644
--- a/src/vs/workbench/contrib/debug/common/replModel.ts
+++ b/src/vs/workbench/contrib/debug/common/replModel.ts
@@ -30,8 +30,12 @@ export class SimpleReplElement implements IReplElement {
 	) { }
 
 	toString(): string {
+		let valueRespectCount = this.value;
+		if (this._count > 1) {
+			valueRespectCount = valueRespectCount + ('\n' + this.value).repeat(this._count - 1);
+		}
 		const sourceStr = this.sourceData ? ` ${this.sourceData.source.name}` : '';
-		return this.value + sourceStr;
+		return valueRespectCount + sourceStr;
 	}
 
 	getId(): string {