diff --git a/src/vs/workbench/contrib/webview/browser/pre/index.html b/src/vs/workbench/contrib/webview/browser/pre/index.html
index 7629db38a295c..0c6829c08f8b0 100644
--- a/src/vs/workbench/contrib/webview/browser/pre/index.html
+++ b/src/vs/workbench/contrib/webview/browser/pre/index.html
@@ -5,7 +5,9 @@
 	<meta charset="UTF-8">
 
 	<meta http-equiv="Content-Security-Policy"
-		content="default-src 'none'; script-src 'sha256-noHVLQsurkONXmA3fcuAmcZ8UPYm/db88mhm9gAXcvk=' 'self'; frame-src 'self'; style-src 'unsafe-inline';">
+
+	content="default-src 'none'; script-src 'sha256-EJBlYt9sOvo6RhZZJG+duTqIZCB8pctk1a62h/ZIElc=' 'self'; frame-src 'self'; style-src 'unsafe-inline';">
+
 
 	<!-- Disable pinch zooming -->
 	<meta name="viewport"
@@ -791,6 +793,17 @@
 			}
 		}
 
+
+		function handleInnerDragEvent(/** @type {DragEvent} */ e) {
+			if (!e.dataTransfer) {
+				return;
+			}
+
+			hostMessaging.postMessage('drag', {
+				shiftKey: e.shiftKey
+			});
+		}
+
 		/**
 		 * @param {() => void} callback
 		 */
@@ -881,7 +894,9 @@
 		window.addEventListener('keydown', handleInnerKeydown);
 		window.addEventListener('keyup', handleInnerKeyup);
 		window.addEventListener('dragenter', handleInnerDragStartEvent);
-		window.addEventListener('dragover', handleInnerDragStartEvent);
+		window.addEventListener('dragover', handleInnerDragEvent);
+		window.addEventListener('drag', handleInnerDragEvent);
+
 
 		onDomReady(() => {
 			if (!document.body) {
@@ -1163,7 +1178,8 @@
 					});
 
 					contentWindow.addEventListener('dragenter', handleInnerDragStartEvent);
-					contentWindow.addEventListener('dragover', handleInnerDragStartEvent);
+					contentWindow.addEventListener('dragover', handleInnerDragEvent);
+					contentWindow.addEventListener('drag', handleInnerDragEvent);
 
 					unloadMonitor.onIframeLoaded(newFrame);
 				}
diff --git a/src/vs/workbench/contrib/webview/browser/webviewElement.ts b/src/vs/workbench/contrib/webview/browser/webviewElement.ts
index 3d5d21f080f7f..5d6e403159f46 100644
--- a/src/vs/workbench/contrib/webview/browser/webviewElement.ts
+++ b/src/vs/workbench/contrib/webview/browser/webviewElement.ts
@@ -34,7 +34,7 @@ import { loadLocalResource, WebviewResourceResponse } from 'vs/workbench/contrib
 import { WebviewThemeDataProvider } from 'vs/workbench/contrib/webview/browser/themeing';
 import { areWebviewContentOptionsEqual, IWebview, WebviewContentOptions, WebviewExtensionDescription, WebviewInitInfo, WebviewMessageReceivedEvent, WebviewOptions } from 'vs/workbench/contrib/webview/browser/webview';
 import { WebviewFindDelegate, WebviewFindWidget } from 'vs/workbench/contrib/webview/browser/webviewFindWidget';
-import { FromWebviewMessage, KeyEvent, ToWebviewMessage } from 'vs/workbench/contrib/webview/browser/webviewMessages';
+import { FromWebviewMessage, KeyEvent, ToWebviewMessage, WebViewDragEvent } from 'vs/workbench/contrib/webview/browser/webviewMessages';
 import { decodeAuthority, webviewGenericCspSource, webviewRootResourceAuthority } from 'vs/workbench/contrib/webview/common/webview';
 import { IWorkbenchEnvironmentService } from 'vs/workbench/services/environment/common/environmentService';
 import { CodeWindow } from 'vs/base/browser/window';
@@ -310,6 +310,10 @@ export class WebviewElement extends Disposable implements IWebview, WebviewFindD
 			this._startBlockingIframeDragEvents();
 		}));
 
+		this._register(this.on('drag', (event) => {
+			this.handleDragEvent('drag', event);
+		}));
+
 		if (initInfo.options.enableFindWidget) {
 			this._webviewFindWidget = this._register(instantiationService.createInstance(WebviewFindWidget, this));
 		}
@@ -697,6 +701,17 @@ export class WebviewElement extends Disposable implements IWebview, WebviewFindD
 		this.window?.dispatchEvent(emulatedKeyboardEvent);
 	}
 
+	private handleDragEvent(type: 'drag', event: WebViewDragEvent) {
+		// Create a fake DragEvent from the data provided
+		const emulatedDragEvent = new DragEvent(type, event);
+		// Force override the target
+		Object.defineProperty(emulatedDragEvent, 'target', {
+			get: () => this.element,
+		});
+		// And re-dispatch
+		this.window?.dispatchEvent(emulatedDragEvent);
+	}
+
 	windowDidDragStart(): void {
 		// Webview break drag and dropping around the main window (no events are generated when you are over them)
 		// Work around this by disabling pointer events during the drag.
diff --git a/src/vs/workbench/contrib/webview/browser/webviewMessages.d.ts b/src/vs/workbench/contrib/webview/browser/webviewMessages.d.ts
index eae9c80fa6872..dde553ec05724 100644
--- a/src/vs/workbench/contrib/webview/browser/webviewMessages.d.ts
+++ b/src/vs/workbench/contrib/webview/browser/webviewMessages.d.ts
@@ -17,6 +17,10 @@ type KeyEvent = {
 	repeat: boolean;
 }
 
+type WebViewDragEvent = {
+	shiftKey: boolean;
+}
+
 export type FromWebviewMessage = {
 	'onmessage': { message: any; transfer?: ArrayBuffer[] };
 	'did-click-link': { uri: string };
@@ -36,6 +40,7 @@ export type FromWebviewMessage = {
 	'did-keyup': KeyEvent;
 	'did-context-menu': { clientX: number; clientY: number; context: { [key: string]: unknown } };
 	'drag-start': void;
+	'drag': WebViewDragEvent
 };
 
 interface UpdateContentEvent {
diff --git a/src/vs/workbench/contrib/webview/browser/webviewWindowDragMonitor.ts b/src/vs/workbench/contrib/webview/browser/webviewWindowDragMonitor.ts
index e4dc5eaf0e904..d009ae186da59 100644
--- a/src/vs/workbench/contrib/webview/browser/webviewWindowDragMonitor.ts
+++ b/src/vs/workbench/contrib/webview/browser/webviewWindowDragMonitor.ts
@@ -18,19 +18,41 @@ export class WebviewWindowDragMonitor extends Disposable {
 	constructor(targetWindow: CodeWindow, getWebview: () => IWebview | undefined) {
 		super();
 
-		this._register(DOM.addDisposableListener(targetWindow, DOM.EventType.DRAG_START, () => {
+		const onDragStart = () => {
 			getWebview()?.windowDidDragStart();
-		}));
+		};
 
 		const onDragEnd = () => {
 			getWebview()?.windowDidDragEnd();
 		};
 
+		this._register(DOM.addDisposableListener(targetWindow, DOM.EventType.DRAG_START, () => {
+			onDragStart();
+		}));
+
 		this._register(DOM.addDisposableListener(targetWindow, DOM.EventType.DRAG_END, onDragEnd));
+
 		this._register(DOM.addDisposableListener(targetWindow, DOM.EventType.MOUSE_MOVE, currentEvent => {
 			if (currentEvent.buttons === 0) {
 				onDragEnd();
 			}
 		}));
+
+		this._register(DOM.addDisposableListener(targetWindow, DOM.EventType.DRAG, (event) => {
+			if (event.shiftKey) {
+				onDragEnd();
+			} else {
+				onDragStart();
+			}
+		}));
+
+		this._register(DOM.addDisposableListener(targetWindow, DOM.EventType.DRAG_OVER, (event) => {
+			if (event.shiftKey) {
+				onDragEnd();
+			} else {
+				onDragStart();
+			}
+		}));
+
 	}
 }