diff --git a/src/vs/base/browser/dom.ts b/src/vs/base/browser/dom.ts
index 272002dd513..7fd1f9b1f14 100644
--- a/src/vs/base/browser/dom.ts
+++ b/src/vs/base/browser/dom.ts
@@ -1042,6 +1042,7 @@ export const EventType = {
 	UNLOAD: 'unload',
 	PAGE_SHOW: 'pageshow',
 	PAGE_HIDE: 'pagehide',
+	PASTE: 'paste',
 	ABORT: 'abort',
 	ERROR: 'error',
 	RESIZE: 'resize',
diff --git a/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts b/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
index 202e523138d..9816031347d 100644
--- a/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
+++ b/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
@@ -116,12 +116,13 @@ KeybindingsRegistry.registerCommandAndKeybindingRule({
 
 const PASTE_FILE_ID = 'filesExplorer.paste';
 
-KeybindingsRegistry.registerCommandAndKeybindingRule({
-	id: PASTE_FILE_ID,
+CommandsRegistry.registerCommand(PASTE_FILE_ID, pasteFileHandler);
+
+KeybindingsRegistry.registerKeybindingRule({
+	id: `^${PASTE_FILE_ID}`, // the `^` enables pasting files into the explorer by preventing default bubble up
 	weight: KeybindingWeight.WorkbenchContrib + explorerCommandsWeightBonus,
 	when: ContextKeyExpr.and(FilesExplorerFocusCondition, ExplorerResourceNotReadonlyContext),
 	primary: KeyMod.CtrlCmd | KeyCode.KeyV,
-	handler: pasteFileHandler
 });
 
 KeybindingsRegistry.registerCommandAndKeybindingRule({
diff --git a/src/vs/workbench/contrib/files/browser/fileActions.ts b/src/vs/workbench/contrib/files/browser/fileActions.ts
index 76c1e965ade..0f153505328 100644
--- a/src/vs/workbench/contrib/files/browser/fileActions.ts
+++ b/src/vs/workbench/contrib/files/browser/fileActions.ts
@@ -5,7 +5,7 @@
 
 import * as nls from 'vs/nls';
 import { isWindows, OperatingSystem, OS } from 'vs/base/common/platform';
-import { extname, basename } from 'vs/base/common/path';
+import { extname, basename, isAbsolute } from 'vs/base/common/path';
 import * as resources from 'vs/base/common/resources';
 import { URI } from 'vs/base/common/uri';
 import { toErrorMessage } from 'vs/base/common/errorMessage';
@@ -1082,7 +1082,7 @@ CommandsRegistry.registerCommand({
 	handler: uploadFileHandler
 });
 
-export const pasteFileHandler = async (accessor: ServicesAccessor) => {
+export const pasteFileHandler = async (accessor: ServicesAccessor, fileList?: FileList) => {
 	const clipboardService = accessor.get(IClipboardService);
 	const explorerService = accessor.get(IExplorerService);
 	const fileService = accessor.get(IFileService);
@@ -1093,7 +1093,34 @@ export const pasteFileHandler = async (accessor: ServicesAccessor) => {
 	const dialogService = accessor.get(IDialogService);
 
 	const context = explorerService.getContext(true);
-	const toPaste = resources.distinctParents(await clipboardService.readResources(), r => r);
+	const hasNativeFilesToPaste = fileList && fileList.length > 0;
+	const confirmPasteNative = hasNativeFilesToPaste && configurationService.getValue<boolean>('explorer.confirmPasteNative');
+
+	const toPaste = await getFilesToPaste(fileList, clipboardService);
+
+	if (confirmPasteNative) {
+		const message = toPaste.length > 1 ?
+			nls.localize('confirmMultiPasteNative', "Are you sure you want to paste the following {0} items?", toPaste.length) :
+			nls.localize('confirmPasteNative', "Are you sure you want to paste '{0}'?", basename(toPaste[0].fsPath));
+		const detail = toPaste.length > 1 ? getFileNamesMessage(toPaste) : undefined;
+		const confirmation = await dialogService.confirm({
+			message,
+			detail,
+			checkbox: {
+				label: nls.localize('doNotAskAgain', "Do not ask me again")
+			},
+			primaryButton: nls.localize({ key: 'pasteButtonLabel', comment: ['&& denotes a mnemonic'] }, "&&Paste")
+		});
+
+		if (!confirmation.confirmed) {
+			return;
+		}
+
+		// Check for confirmation checkbox
+		if (confirmation.checkboxChecked === true) {
+			await configurationService.updateValue('explorer.confirmPasteNative', false);
+		}
+	}
 	const element = context.length ? context[0] : explorerService.roots[0];
 	const incrementalNaming = configurationService.getValue<IFilesConfiguration>().explorer.incrementalNaming;
 
@@ -1175,6 +1202,16 @@ export const pasteFileHandler = async (accessor: ServicesAccessor) => {
 	}
 };
 
+async function getFilesToPaste(fileList: FileList | undefined, clipboardService: IClipboardService): Promise<readonly URI[]> {
+	if (fileList) {
+		// with a `fileList` we support natively pasting files from clipboard
+		return [...fileList].filter(file => !!file.path && isAbsolute(file.path)).map(file => URI.file(file.path));
+	} else {
+		// otherwise we fallback to reading resources from our clipboard service
+		return resources.distinctParents(await clipboardService.readResources(), resource => resource);
+	}
+}
+
 export const openFilePreserveFocusHandler = async (accessor: ServicesAccessor) => {
 	const editorService = accessor.get(IEditorService);
 	const explorerService = accessor.get(IExplorerService);
diff --git a/src/vs/workbench/contrib/files/browser/files.contribution.ts b/src/vs/workbench/contrib/files/browser/files.contribution.ts
index 8423b6b046f..985ef683fce 100644
--- a/src/vs/workbench/contrib/files/browser/files.contribution.ts
+++ b/src/vs/workbench/contrib/files/browser/files.contribution.ts
@@ -444,6 +444,11 @@ configurationRegistry.registerConfiguration({
 			'description': nls.localize('confirmDragAndDrop', "Controls whether the Explorer should ask for confirmation to move files and folders via drag and drop."),
 			'default': true
 		},
+		'explorer.confirmPasteNative': {
+			'type': 'boolean',
+			'description': nls.localize('confirmPasteNative', "Controls whether the Explorer should ask for confirmation when pasting native files and folders."),
+			'default': true
+		},
 		'explorer.confirmDelete': {
 			'type': 'boolean',
 			'description': nls.localize('confirmDelete', "Controls whether the Explorer should ask for confirmation when deleting a file via the trash."),
diff --git a/src/vs/workbench/contrib/files/browser/views/explorerView.ts b/src/vs/workbench/contrib/files/browser/views/explorerView.ts
index ba439a3585c..fcc5cb9631e 100644
--- a/src/vs/workbench/contrib/files/browser/views/explorerView.ts
+++ b/src/vs/workbench/contrib/files/browser/views/explorerView.ts
@@ -321,6 +321,15 @@ export class ExplorerView extends ViewPane implements IExplorerView {
 				this.selectActiveFile(true);
 			}
 		}));
+
+		// Support for paste of files into explorer
+		this._register(DOM.addDisposableListener(DOM.getWindow(this.container), DOM.EventType.PASTE, async event => {
+			if (!this.hasFocus() || this.readonlyContext.get()) {
+				return;
+			}
+
+			await this.commandService.executeCommand('filesExplorer.paste', event.clipboardData?.files);
+		}));
 	}
 
 	override focus(): void {