diff --git a/extensions/markdown-language-features/package.json b/extensions/markdown-language-features/package.json
index dbc8746c913e9da05eb0b0b5997edcba1295255b..541cd4e327a533bf1cb9d8e6d529999d9b2ac654 100644
--- a/extensions/markdown-language-features/package.json
+++ b/extensions/markdown-language-features/package.json
@@ -312,7 +312,7 @@
 		"customEditors": [
 			{
 				"viewType": "vscode.markdown.preview.editor",
-				"displayName": "(Experimental) VS Code Markdown Preview",
+				"displayName": "Markdown Preview (Experimental)",
 				"priority": "option",
 				"selector": [
 					{
diff --git a/src/vs/workbench/api/browser/mainThreadEditors.ts b/src/vs/workbench/api/browser/mainThreadEditors.ts
index f7b2c2f13276d443ffb682224638ce4d5d103379..f178c2f2b516fd5f681085c4fef183c733264097 100644
--- a/src/vs/workbench/api/browser/mainThreadEditors.ts
+++ b/src/vs/workbench/api/browser/mainThreadEditors.ts
@@ -24,7 +24,9 @@ import { ExtHostContext, ExtHostEditorsShape, IApplyEditsOptions, IExtHostContex
 import { EditorViewColumn, editorGroupToViewColumn, viewColumnToEditorGroup } from 'vs/workbench/api/common/shared/editor';
 import { IEditorService } from 'vs/workbench/services/editor/common/editorService';
 import { IEditorGroupsService } from 'vs/workbench/services/editor/common/editorGroupsService';
-import { DEFAULT_EDITOR_ID } from 'vs/workbench/contrib/files/common/files';
+import { openEditorWith } from 'vs/workbench/contrib/files/common/openWith';
+import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
+import { IQuickInputService } from 'vs/platform/quickinput/common/quickInput';
 
 export class MainThreadTextEditors implements MainThreadTextEditorsShape {
 
@@ -296,26 +298,17 @@ CommandsRegistry.registerCommand('_workbench.open', function (accessor: Services
 
 CommandsRegistry.registerCommand('_workbench.openWith', (accessor: ServicesAccessor, args: [URI, string, ITextEditorOptions | undefined, EditorViewColumn | undefined]) => {
 	const editorService = accessor.get(IEditorService);
-	const editorGroupService = accessor.get(IEditorGroupsService);
+	const editorGroupsService = accessor.get(IEditorGroupsService);
+	const configurationService = accessor.get(IConfigurationService);
+	const quickInputService = accessor.get(IQuickInputService);
 
 	const [resource, id, options, position] = args;
 
-	const group = editorGroupService.getGroup(viewColumnToEditorGroup(editorGroupService, position)) ?? editorGroupService.activeGroup;
+	const group = editorGroupsService.getGroup(viewColumnToEditorGroup(editorGroupsService, position)) ?? editorGroupsService.activeGroup;
 	const textOptions = options ? { ...options, ignoreOverrides: true } : { ignoreOverrides: true };
 
-	const fileEditorInput = editorService.createEditorInput({ resource, forceFile: true });
-	if (id === DEFAULT_EDITOR_ID) {
-		return editorService.openEditor(fileEditorInput, textOptions, position);
-	}
-
-	const editors = editorService.getEditorOverrides(fileEditorInput, undefined, group);
-	for (const [handler, data] of editors) {
-		if (data.id === id) {
-			return handler.open(fileEditorInput, options, group, id);
-		}
-	}
-
-	return undefined;
+	const input = editorService.createEditorInput({ resource });
+	return openEditorWith(input, id, textOptions, group, editorService, configurationService, quickInputService);
 });
 
 
diff --git a/src/vs/workbench/browser/contextkeys.ts b/src/vs/workbench/browser/contextkeys.ts
index ce9fcaf3c0d42128f18c1cc2801f0363c81475be..78755ab325eba90f0e0e5e5cc22ed17cefc9269a 100644
--- a/src/vs/workbench/browser/contextkeys.ts
+++ b/src/vs/workbench/browser/contextkeys.ts
@@ -7,7 +7,7 @@ import { Event } from 'vs/base/common/event';
 import { Disposable } from 'vs/base/common/lifecycle';
 import { IContextKeyService, IContextKey, RawContextKey } from 'vs/platform/contextkey/common/contextkey';
 import { InputFocusedContext, IsMacContext, IsLinuxContext, IsWindowsContext, IsWebContext, IsMacNativeContext, IsDevelopmentContext } from 'vs/platform/contextkey/common/contextkeys';
-import { ActiveEditorContext, EditorsVisibleContext, TextCompareEditorVisibleContext, TextCompareEditorActiveContext, ActiveEditorGroupEmptyContext, MultipleEditorGroupsContext, TEXT_DIFF_EDITOR_ID, SplitEditorsVertically, InEditorZenModeContext, IsCenteredLayoutContext, ActiveEditorGroupIndexContext, ActiveEditorGroupLastContext, ActiveEditorIsReadonlyContext, EditorAreaVisibleContext, DirtyWorkingCopiesContext, ActiveEditorAvailableEditorsContext } from 'vs/workbench/common/editor';
+import { ActiveEditorContext, EditorsVisibleContext, TextCompareEditorVisibleContext, TextCompareEditorActiveContext, ActiveEditorGroupEmptyContext, MultipleEditorGroupsContext, TEXT_DIFF_EDITOR_ID, SplitEditorsVertically, InEditorZenModeContext, IsCenteredLayoutContext, ActiveEditorGroupIndexContext, ActiveEditorGroupLastContext, ActiveEditorIsReadonlyContext, EditorAreaVisibleContext, DirtyWorkingCopiesContext, ActiveEditorAvailableEditorIdsContext } from 'vs/workbench/common/editor';
 import { trackFocus, addDisposableListener, EventType } from 'vs/base/browser/dom';
 import { preferredSideBySideGroupDirection, GroupDirection, IEditorGroupsService } from 'vs/workbench/services/editor/common/editorGroupsService';
 import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
@@ -41,7 +41,7 @@ export class WorkbenchContextKeysHandler extends Disposable {
 
 	private activeEditorContext: IContextKey<string | null>;
 	private activeEditorIsReadonly: IContextKey<boolean>;
-	private activeEditorAvailableEditors: IContextKey<string>;
+	private activeEditorAvailableEditorIds: IContextKey<string>;
 
 	private activeEditorGroupEmpty: IContextKey<boolean>;
 	private activeEditorGroupIndex: IContextKey<number>;
@@ -92,7 +92,7 @@ export class WorkbenchContextKeysHandler extends Disposable {
 		// Editors
 		this.activeEditorContext = ActiveEditorContext.bindTo(this.contextKeyService);
 		this.activeEditorIsReadonly = ActiveEditorIsReadonlyContext.bindTo(this.contextKeyService);
-		this.activeEditorAvailableEditors = ActiveEditorAvailableEditorsContext.bindTo(this.contextKeyService);
+		this.activeEditorAvailableEditorIds = ActiveEditorAvailableEditorIdsContext.bindTo(this.contextKeyService);
 		this.editorsVisibleContext = EditorsVisibleContext.bindTo(this.contextKeyService);
 		this.textCompareEditorVisibleContext = TextCompareEditorVisibleContext.bindTo(this.contextKeyService);
 		this.textCompareEditorActiveContext = TextCompareEditorActiveContext.bindTo(this.contextKeyService);
@@ -211,11 +211,11 @@ export class WorkbenchContextKeysHandler extends Disposable {
 			this.activeEditorIsReadonly.set(activeEditorPane.input.isReadonly());
 
 			const editors = this.editorService.getEditorOverrides(activeEditorPane.input, undefined, activeGroup);
-			this.activeEditorAvailableEditors.set(editors.map(([_, entry]) => entry.id).join(','));
+			this.activeEditorAvailableEditorIds.set(editors.map(([_, entry]) => entry.id).join(','));
 		} else {
 			this.activeEditorContext.reset();
 			this.activeEditorIsReadonly.reset();
-			this.activeEditorAvailableEditors.reset();
+			this.activeEditorAvailableEditorIds.reset();
 		}
 	}
 
diff --git a/src/vs/workbench/common/editor.ts b/src/vs/workbench/common/editor.ts
index 56c7e830f47b7189804c7d9c58e96d7f4c6ac891..3618cecdb3a803694a9faa440380bff981d98348 100644
--- a/src/vs/workbench/common/editor.ts
+++ b/src/vs/workbench/common/editor.ts
@@ -32,7 +32,7 @@ import { IFilesConfigurationService, AutoSaveMode } from 'vs/workbench/services/
 export const DirtyWorkingCopiesContext = new RawContextKey<boolean>('dirtyWorkingCopies', false);
 export const ActiveEditorContext = new RawContextKey<string | null>('activeEditor', null);
 export const ActiveEditorIsReadonlyContext = new RawContextKey<boolean>('activeEditorIsReadonly', false);
-export const ActiveEditorAvailableEditorsContext = new RawContextKey<string>('availableEditors', '');
+export const ActiveEditorAvailableEditorIdsContext = new RawContextKey<string>('activeEditorAvailableEditorIds', '');
 export const EditorsVisibleContext = new RawContextKey<boolean>('editorIsOpen', false);
 export const EditorPinnedContext = new RawContextKey<boolean>('editorPinned', false);
 export const EditorGroupActiveEditorDirtyContext = new RawContextKey<boolean>('groupActiveEditorDirty', false);
diff --git a/src/vs/workbench/contrib/customEditor/browser/customEditors.ts b/src/vs/workbench/contrib/customEditor/browser/customEditors.ts
index 0c2b2904f64685f10f8fd471797f44da9b9a4140..a275ead51a0544a14e14bfa98205c804a735d018 100644
--- a/src/vs/workbench/contrib/customEditor/browser/customEditors.ts
+++ b/src/vs/workbench/contrib/customEditor/browser/customEditors.ts
@@ -27,7 +27,7 @@ import { CONTEXT_CUSTOM_EDITORS, CONTEXT_FOCUSED_CUSTOM_EDITOR_IS_EDITABLE, Cust
 import { CustomEditorModelManager } from 'vs/workbench/contrib/customEditor/common/customEditorModelManager';
 import { FileEditorInput } from 'vs/workbench/contrib/files/common/editors/fileEditorInput';
 import { IWebviewService, webviewHasOwnEditFunctionsContext } from 'vs/workbench/contrib/webview/browser/webview';
-import { CustomEditorAssociation, CustomEditorsAssociations, customEditorsAssociationsSettingId } from 'vs/workbench/services/editor/browser/editorAssociationsSetting';
+import { CustomEditorAssociation, CustomEditorsAssociations, customEditorsAssociationsSettingId } from 'vs/workbench/services/editor/common/editorAssociationsSetting';
 import { IEditorGroup, IEditorGroupsService } from 'vs/workbench/services/editor/common/editorGroupsService';
 import { ICustomEditorInfo, ICustomEditorViewTypesHandler, IEditorService, IOpenEditorOverride, IOpenEditorOverrideEntry } from 'vs/workbench/services/editor/common/editorService';
 import { ContributedCustomEditors, defaultCustomEditor } from '../common/contributedCustomEditors';
diff --git a/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts b/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
index 4aa40aa792069d0966aa09adc42420a42c82e2c7..f2051f2a7189938a7eacbc03a63bc70ac5294412 100644
--- a/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
+++ b/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
@@ -10,12 +10,12 @@ import { revertLocalChangesCommand, acceptLocalChangesCommand, CONFLICT_RESOLUTI
 import { SyncActionDescriptor, MenuId, MenuRegistry, ILocalizedString } from 'vs/platform/actions/common/actions';
 import { IWorkbenchActionRegistry, Extensions as ActionExtensions } from 'vs/workbench/common/actions';
 import { KeyMod, KeyChord, KeyCode } from 'vs/base/common/keyCodes';
-import { openWindowCommand, COPY_PATH_COMMAND_ID, REVEAL_IN_EXPLORER_COMMAND_ID, OPEN_TO_SIDE_COMMAND_ID, REVERT_FILE_COMMAND_ID, SAVE_FILE_COMMAND_ID, SAVE_FILE_LABEL, SAVE_FILE_AS_COMMAND_ID, SAVE_FILE_AS_LABEL, SAVE_ALL_IN_GROUP_COMMAND_ID, OpenEditorsGroupContext, COMPARE_WITH_SAVED_COMMAND_ID, COMPARE_RESOURCE_COMMAND_ID, SELECT_FOR_COMPARE_COMMAND_ID, ResourceSelectedForCompareContext, DirtyEditorContext, COMPARE_SELECTED_COMMAND_ID, REMOVE_ROOT_FOLDER_COMMAND_ID, REMOVE_ROOT_FOLDER_LABEL, SAVE_FILES_COMMAND_ID, COPY_RELATIVE_PATH_COMMAND_ID, SAVE_FILE_WITHOUT_FORMATTING_COMMAND_ID, SAVE_FILE_WITHOUT_FORMATTING_LABEL, newWindowCommand, ReadonlyEditorContext } from 'vs/workbench/contrib/files/browser/fileCommands';
+import { openWindowCommand, COPY_PATH_COMMAND_ID, REVEAL_IN_EXPLORER_COMMAND_ID, OPEN_TO_SIDE_COMMAND_ID, REVERT_FILE_COMMAND_ID, SAVE_FILE_COMMAND_ID, SAVE_FILE_LABEL, SAVE_FILE_AS_COMMAND_ID, SAVE_FILE_AS_LABEL, SAVE_ALL_IN_GROUP_COMMAND_ID, OpenEditorsGroupContext, COMPARE_WITH_SAVED_COMMAND_ID, COMPARE_RESOURCE_COMMAND_ID, SELECT_FOR_COMPARE_COMMAND_ID, ResourceSelectedForCompareContext, DirtyEditorContext, COMPARE_SELECTED_COMMAND_ID, REMOVE_ROOT_FOLDER_COMMAND_ID, REMOVE_ROOT_FOLDER_LABEL, SAVE_FILES_COMMAND_ID, COPY_RELATIVE_PATH_COMMAND_ID, SAVE_FILE_WITHOUT_FORMATTING_COMMAND_ID, SAVE_FILE_WITHOUT_FORMATTING_LABEL, newWindowCommand, ReadonlyEditorContext, OPEN_WITH_EXPLORER_COMMAND_ID } from 'vs/workbench/contrib/files/browser/fileCommands';
 import { CommandsRegistry, ICommandHandler } from 'vs/platform/commands/common/commands';
 import { ContextKeyExpr, ContextKeyExpression } from 'vs/platform/contextkey/common/contextkey';
 import { KeybindingsRegistry, KeybindingWeight } from 'vs/platform/keybinding/common/keybindingsRegistry';
 import { isMacintosh } from 'vs/base/common/platform';
-import { FilesExplorerFocusCondition, ExplorerRootContext, ExplorerFolderContext, ExplorerResourceNotReadonlyContext, ExplorerResourceCut, IExplorerService, ExplorerResourceMoveableToTrash, ExplorerViewletVisibleContext } from 'vs/workbench/contrib/files/common/files';
+import { FilesExplorerFocusCondition, ExplorerRootContext, ExplorerFolderContext, ExplorerResourceNotReadonlyContext, ExplorerResourceCut, IExplorerService, ExplorerResourceMoveableToTrash, ExplorerViewletVisibleContext, ExplorerResourceAvailableEditorIdsContext } from 'vs/workbench/contrib/files/common/files';
 import { ADD_ROOT_FOLDER_COMMAND_ID, ADD_ROOT_FOLDER_LABEL } from 'vs/workbench/browser/actions/workspaceCommands';
 import { CLOSE_SAVED_EDITORS_COMMAND_ID, CLOSE_EDITORS_IN_GROUP_COMMAND_ID, CLOSE_EDITOR_COMMAND_ID, CLOSE_OTHER_EDITORS_IN_GROUP_COMMAND_ID } from 'vs/workbench/browser/parts/editor/editorCommands';
 import { AutoSaveAfterShortDelayContext } from 'vs/workbench/services/filesConfiguration/common/filesConfigurationService';
@@ -26,7 +26,7 @@ import { WorkspaceFolderCountContext } from 'vs/workbench/browser/contextkeys';
 import { IsWebContext } from 'vs/platform/contextkey/common/contextkeys';
 import { ServicesAccessor } from 'vs/platform/instantiation/common/instantiation';
 import { OpenFileFolderAction, OpenFileAction, OpenFolderAction, OpenWorkspaceAction } from 'vs/workbench/browser/actions/workspaceActions';
-import { ActiveEditorIsReadonlyContext, DirtyWorkingCopiesContext, ActiveEditorContext, ActiveEditorAvailableEditorsContext } from 'vs/workbench/common/editor';
+import { ActiveEditorIsReadonlyContext, DirtyWorkingCopiesContext, ActiveEditorContext, ActiveEditorAvailableEditorIdsContext } from 'vs/workbench/common/editor';
 import { SidebarFocusContext } from 'vs/workbench/common/viewlet';
 import { ThemeIcon } from 'vs/platform/theme/common/themeService';
 
@@ -36,7 +36,7 @@ const category = { value: nls.localize('filesCategory', "File"), original: 'File
 const registry = Registry.as<IWorkbenchActionRegistry>(ActionExtensions.WorkbenchActions);
 registry.registerWorkbenchAction(SyncActionDescriptor.from(SaveAllAction, { primary: undefined, mac: { primary: KeyMod.CtrlCmd | KeyMod.Alt | KeyCode.KEY_S }, win: { primary: KeyChord(KeyMod.CtrlCmd | KeyCode.KEY_K, KeyCode.KEY_S) } }), 'File: Save All', category.value);
 registry.registerWorkbenchAction(SyncActionDescriptor.from(GlobalCompareResourcesAction), 'File: Compare Active File With...', category.value);
-registry.registerWorkbenchAction(SyncActionDescriptor.from(ReopenResourcesAction), 'File: Reopen With...', category.value, ActiveEditorAvailableEditorsContext);
+registry.registerWorkbenchAction(SyncActionDescriptor.from(ReopenResourcesAction), 'File: Reopen With...', category.value, ActiveEditorAvailableEditorIdsContext);
 registry.registerWorkbenchAction(SyncActionDescriptor.from(FocusFilesExplorer), 'File: Focus on Files Explorer', category.value);
 registry.registerWorkbenchAction(SyncActionDescriptor.from(ShowActiveFileInExplorer), 'File: Reveal Active File in Side Bar', category.value);
 registry.registerWorkbenchAction(SyncActionDescriptor.from(CollapseExplorerView), 'File: Collapse Folders in Explorer', category.value);
@@ -192,7 +192,7 @@ MenuRegistry.appendMenuItem(MenuId.EditorTitle, {
 	},
 	group: '6_reopen',
 	order: 20,
-	when: ActiveEditorAvailableEditorsContext,
+	when: ActiveEditorAvailableEditorIdsContext,
 });
 
 // Editor Title Menu for Conflict Resolution
@@ -435,6 +435,16 @@ MenuRegistry.appendMenuItem(MenuId.ExplorerContext, {
 	when: ContextKeyExpr.and(ExplorerFolderContext.toNegated(), ResourceContextKey.HasResource)
 });
 
+MenuRegistry.appendMenuItem(MenuId.ExplorerContext, {
+	group: 'navigation',
+	order: 20,
+	command: {
+		id: OPEN_WITH_EXPLORER_COMMAND_ID,
+		title: nls.localize('explorerOpenWith', "Open With..."),
+	},
+	when: ContextKeyExpr.and(ExplorerRootContext.toNegated(), ExplorerResourceAvailableEditorIdsContext),
+});
+
 MenuRegistry.appendMenuItem(MenuId.ExplorerContext, {
 	group: '3_compare',
 	order: 20,
diff --git a/src/vs/workbench/contrib/files/browser/fileActions.ts b/src/vs/workbench/contrib/files/browser/fileActions.ts
index 5608ef032570bb16187496c9686d19ec7b99771c..831932459b32b20e3b456718d8a8bd1be0c38e7e 100644
--- a/src/vs/workbench/contrib/files/browser/fileActions.ts
+++ b/src/vs/workbench/contrib/files/browser/fileActions.ts
@@ -13,12 +13,12 @@ import { toErrorMessage } from 'vs/base/common/errorMessage';
 import * as strings from 'vs/base/common/strings';
 import { Action } from 'vs/base/common/actions';
 import { dispose, IDisposable } from 'vs/base/common/lifecycle';
-import { VIEWLET_ID, IExplorerService, IFilesConfiguration, DEFAULT_EDITOR_ID } from 'vs/workbench/contrib/files/common/files';
+import { VIEWLET_ID, IExplorerService, IFilesConfiguration } from 'vs/workbench/contrib/files/common/files';
 import { ITextFileService } from 'vs/workbench/services/textfile/common/textfiles';
 import { IFileService } from 'vs/platform/files/common/files';
 import { toResource, SideBySideEditor, IEditorInput } from 'vs/workbench/common/editor';
 import { ExplorerViewPaneContainer } from 'vs/workbench/contrib/files/browser/explorerViewlet';
-import { IQuickInputService, ItemActivation, IQuickPickItem } from 'vs/platform/quickinput/common/quickInput';
+import { IQuickInputService, ItemActivation } from 'vs/platform/quickinput/common/quickInput';
 import { IViewletService } from 'vs/workbench/services/viewlet/browser/viewlet';
 import { IInstantiationService, ServicesAccessor } from 'vs/platform/instantiation/common/instantiation';
 import { ITextModel } from 'vs/editor/common/model';
@@ -34,7 +34,7 @@ import { RawContextKey } from 'vs/platform/contextkey/common/contextkey';
 import { Schemas } from 'vs/base/common/network';
 import { IDialogService, IConfirmationResult, getFileNamesMessage, IFileDialogService } from 'vs/platform/dialogs/common/dialogs';
 import { INotificationService, Severity } from 'vs/platform/notification/common/notification';
-import { IEditorService, IOpenEditorOverrideHandler } from 'vs/workbench/services/editor/common/editorService';
+import { IEditorService } from 'vs/workbench/services/editor/common/editorService';
 import { Constants } from 'vs/base/common/uint';
 import { CLOSE_EDITORS_AND_GROUP_COMMAND_ID } from 'vs/workbench/browser/parts/editor/editorCommands';
 import { coalesce } from 'vs/base/common/arrays';
@@ -49,9 +49,8 @@ import { IWorkingCopyFileService } from 'vs/workbench/services/workingCopy/commo
 import { once } from 'vs/base/common/functional';
 import { IEditorOptions } from 'vs/platform/editor/common/editor';
 import { IEditorGroup } from 'vs/workbench/services/editor/common/editorGroupsService';
-import { FileEditorInput } from 'vs/workbench/contrib/files/common/editors/fileEditorInput';
 import { Codicon } from 'vs/base/common/codicons';
-import { CustomEditorsAssociations, customEditorsAssociationsSettingId, CustomEditorAssociation } from 'vs/workbench/services/editor/browser/editorAssociationsSetting';
+import { openEditorWith } from 'vs/workbench/contrib/files/common/openWith';
 
 export const NEW_FILE_COMMAND_ID = 'explorer.newFile';
 export const NEW_FILE_LABEL = nls.localize('newFile', "New File");
@@ -521,7 +520,6 @@ export class GlobalCompareResourcesAction extends Action {
 	}
 }
 
-const builtinProviderDisplayName = nls.localize('builtinProviderDisplayName', "Built-in");
 export class ReopenResourcesAction extends Action {
 
 	static readonly ID = 'workbench.files.action.reopenWithEditor';
@@ -550,98 +548,7 @@ export class ReopenResourcesAction extends Action {
 
 		const options = activeEditorPane.options;
 		const group = activeEditorPane.group;
-		const activeResource = activeInput.resource;
-		if (!activeResource) {
-			return;
-		}
-
-		const resourceExt = extname(activeResource.path);
-
-		const overrides = this.editorService.getEditorOverrides(activeInput, options, group);
-		const items: (IQuickPickItem & { handler?: IOpenEditorOverrideHandler })[] = overrides.map((override) => {
-			return {
-				handler: override[0],
-				id: override[1].id,
-				label: override[1].label,
-				description: override[1].active ? 'Currently Active' : undefined,
-				detail: override[1].detail,
-				buttons: resourceExt ? [{
-					iconClass: 'codicon-settings-gear',
-					tooltip: nls.localize('promptOpenWith.setDefaultTooltip', "Set as default editor for '{0}' files", resourceExt)
-				}] : undefined
-			};
-		});
-
-		if (!items.length) {
-			return;
-		}
-
-		if (!items.find(item => item.id === DEFAULT_EDITOR_ID)) {
-			items.unshift({
-				id: DEFAULT_EDITOR_ID,
-				label: nls.localize('promptOpenWith.defaultEditor.displayName', "Text Editor"),
-				description: activeInput instanceof FileEditorInput ? 'Currently Active' : undefined,
-				detail: builtinProviderDisplayName,
-				buttons: resourceExt ? [{
-					iconClass: 'codicon-settings-gear',
-					tooltip: nls.localize('promptOpenWith.setDefaultTooltip', "Set as default editor for '{0}' files", resourceExt)
-				}] : undefined
-			});
-		}
-
-		const picker = this.quickInputService.createQuickPick<(IQuickPickItem & { handler?: IOpenEditorOverrideHandler })>();
-		picker.items = items;
-		picker.placeholder = nls.localize('promptOpenWith.placeHolder', "Select editor to use for '{0}'...", resources.basename(activeResource));
-
-		const pickedItem = await new Promise<(IQuickPickItem & { handler?: IOpenEditorOverrideHandler }) | undefined>(resolve => {
-			picker.onDidAccept(() => {
-				resolve(picker.selectedItems.length === 1 ? picker.selectedItems[0] : undefined);
-				picker.dispose();
-			});
-
-			picker.onDidTriggerItemButton(e => {
-				const pick = e.item;
-				const id = pick.id;
-				resolve(pick); // open the view
-				picker.dispose();
-
-				// And persist the setting
-				if (pick && id) {
-					const newAssociation: CustomEditorAssociation = { viewType: id, filenamePattern: '*' + resourceExt };
-					const currentAssociations = [...this.configurationService.getValue<CustomEditorsAssociations>(customEditorsAssociationsSettingId)];
-
-					// First try updating existing association
-					for (let i = 0; i < currentAssociations.length; ++i) {
-						const existing = currentAssociations[i];
-						if (existing.filenamePattern === newAssociation.filenamePattern) {
-							currentAssociations.splice(i, 1, newAssociation);
-							this.configurationService.updateValue(customEditorsAssociationsSettingId, currentAssociations);
-							return;
-						}
-					}
-
-					// Otherwise, create a new one
-					currentAssociations.unshift(newAssociation);
-					this.configurationService.updateValue(customEditorsAssociationsSettingId, currentAssociations);
-				}
-			});
-
-			picker.show();
-		});
-
-		if (!pickedItem) {
-			return;
-		}
-
-		if (pickedItem.id === DEFAULT_EDITOR_ID) {
-			const fileEditorInput = this.editorService.createEditorInput({ resource: activeResource!, forceFile: true });
-			const textOptions = options ? { ...options, ignoreOverrides: true } : { ignoreOverrides: true };
-
-			await this.editorService.openEditor(fileEditorInput, textOptions, group);
-			return;
-		}
-
-		await pickedItem.handler!.open(activeInput!, options, group, pickedItem.id);
+		return openEditorWith(activeInput, undefined, options, group, this.editorService, this.configurationService, this.quickInputService);
 	}
 }
 
diff --git a/src/vs/workbench/contrib/files/browser/fileCommands.ts b/src/vs/workbench/contrib/files/browser/fileCommands.ts
index b02a9a4b480ba9a6c58e61b0b99e2ef202d18172..fbca13d1641521589674e59f380c2fc3805026f5 100644
--- a/src/vs/workbench/contrib/files/browser/fileCommands.ts
+++ b/src/vs/workbench/contrib/files/browser/fileCommands.ts
@@ -40,12 +40,16 @@ import { coalesce } from 'vs/base/common/arrays';
 import { ICodeEditorService } from 'vs/editor/browser/services/codeEditorService';
 import { EmbeddedCodeEditorWidget } from 'vs/editor/browser/widget/embeddedCodeEditorWidget';
 import { ITextFileService } from 'vs/workbench/services/textfile/common/textfiles';
+import { openEditorWith } from 'vs/workbench/contrib/files/common/openWith';
+import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
+import { IQuickInputService } from 'vs/platform/quickinput/common/quickInput';
 
 // Commands
 
 export const REVEAL_IN_EXPLORER_COMMAND_ID = 'revealInExplorer';
 export const REVERT_FILE_COMMAND_ID = 'workbench.action.files.revert';
 export const OPEN_TO_SIDE_COMMAND_ID = 'explorer.openToSide';
+export const OPEN_WITH_EXPLORER_COMMAND_ID = 'explorer.openWith';
 export const SELECT_FOR_COMPARE_COMMAND_ID = 'selectForCompare';
 
 export const COMPARE_SELECTED_COMMAND_ID = 'compareSelected';
@@ -313,6 +317,22 @@ CommandsRegistry.registerCommand({
 	}
 });
 
+CommandsRegistry.registerCommand({
+	id: OPEN_WITH_EXPLORER_COMMAND_ID,
+	handler: async (accessor, resource: URI | object) => {
+		const editorService = accessor.get(IEditorService);
+		const editorGroupsService = accessor.get(IEditorGroupsService);
+		const configurationService = accessor.get(IConfigurationService);
+		const quickInputService = accessor.get(IQuickInputService);
+
+		const uri = getResourceForCommand(resource, accessor.get(IListService), accessor.get(IEditorService));
+		if (uri) {
+			const input = editorService.createEditorInput({ resource: uri });
+			openEditorWith(input, undefined, undefined, editorGroupsService.activeGroup, editorService, configurationService, quickInputService);
+		}
+	}
+});
+
 // Save / Save As / Save All / Revert
 
 async function saveSelectedEditors(accessor: ServicesAccessor, options?: ISaveEditorsOptions): Promise<void> {
diff --git a/src/vs/workbench/contrib/files/browser/views/explorerView.ts b/src/vs/workbench/contrib/files/browser/views/explorerView.ts
index 1305fa87a3bef07fd46bb85d616df77a4cc7316e..ccc937a8ec24ad87c0a4762d914064c9d19c3cc1 100644
--- a/src/vs/workbench/contrib/files/browser/views/explorerView.ts
+++ b/src/vs/workbench/contrib/files/browser/views/explorerView.ts
@@ -8,7 +8,7 @@ import { URI } from 'vs/base/common/uri';
 import * as perf from 'vs/base/common/performance';
 import { IAction, WorkbenchActionExecutedEvent, WorkbenchActionExecutedClassification } from 'vs/base/common/actions';
 import { memoize } from 'vs/base/common/decorators';
-import { IFilesConfiguration, ExplorerFolderContext, FilesExplorerFocusedContext, ExplorerFocusedContext, ExplorerRootContext, ExplorerResourceReadonlyContext, IExplorerService, ExplorerResourceCut, ExplorerResourceMoveableToTrash, ExplorerCompressedFocusContext, ExplorerCompressedFirstFocusContext, ExplorerCompressedLastFocusContext } from 'vs/workbench/contrib/files/common/files';
+import { IFilesConfiguration, ExplorerFolderContext, FilesExplorerFocusedContext, ExplorerFocusedContext, ExplorerRootContext, ExplorerResourceReadonlyContext, IExplorerService, ExplorerResourceCut, ExplorerResourceMoveableToTrash, ExplorerCompressedFocusContext, ExplorerCompressedFirstFocusContext, ExplorerCompressedLastFocusContext, ExplorerResourceAvailableEditorIdsContext } from 'vs/workbench/contrib/files/common/files';
 import { NewFolderAction, NewFileAction, FileCopiedContext, RefreshExplorerView, CollapseExplorerView } from 'vs/workbench/contrib/files/browser/fileActions';
 import { toResource, SideBySideEditor } from 'vs/workbench/common/editor';
 import { DiffEditorInput } from 'vs/workbench/common/editor/diffEditorInput';
@@ -132,6 +132,8 @@ export class ExplorerView extends ViewPane {
 	private resourceContext: ResourceContextKey;
 	private folderContext: IContextKey<boolean>;
 	private readonlyContext: IContextKey<boolean>;
+	private availableEditorIdsContext: IContextKey<string>;
+
 	private rootContext: IContextKey<boolean>;
 	private resourceMoveableToTrash: IContextKey<boolean>;
 
@@ -179,6 +181,7 @@ export class ExplorerView extends ViewPane {
 
 		this.folderContext = ExplorerFolderContext.bindTo(contextKeyService);
 		this.readonlyContext = ExplorerResourceReadonlyContext.bindTo(contextKeyService);
+		this.availableEditorIdsContext = ExplorerResourceAvailableEditorIdsContext.bindTo(contextKeyService);
 		this.rootContext = ExplorerRootContext.bindTo(contextKeyService);
 		this.resourceMoveableToTrash = ExplorerResourceMoveableToTrash.bindTo(contextKeyService);
 		this.compressedFocusContext = ExplorerCompressedFocusContext.bindTo(contextKeyService);
@@ -473,6 +476,14 @@ export class ExplorerView extends ViewPane {
 		this.folderContext.set((isSingleFolder && !stat) || !!stat && stat.isDirectory);
 		this.readonlyContext.set(!!stat && stat.isReadonly);
 		this.rootContext.set(!stat || (stat && stat.isRoot));
+
+		if (resource) {
+			const fileEditorInput = this.editorService.createEditorInput({ resource, forceFile: true });
+			const overrides = this.editorService.getEditorOverrides(fileEditorInput, undefined, undefined);
+			this.availableEditorIdsContext.set(overrides.map(([, entry]) => entry.id).join(','));
+		} else {
+			this.availableEditorIdsContext.reset();
+		}
 	}
 
 	private onContextMenu(e: ITreeContextMenuEvent<ExplorerItem>): void {
diff --git a/src/vs/workbench/contrib/files/common/files.ts b/src/vs/workbench/contrib/files/common/files.ts
index 8af67e372382ff68673faf918ae8fcdc07c3ab19..449c6b86486456a146906863c03a71941aa7d6de 100644
--- a/src/vs/workbench/contrib/files/common/files.ts
+++ b/src/vs/workbench/contrib/files/common/files.ts
@@ -77,6 +77,10 @@ export const ExplorerViewletVisibleContext = new RawContextKey<boolean>('explore
 export const ExplorerFolderContext = new RawContextKey<boolean>('explorerResourceIsFolder', false);
 export const ExplorerResourceReadonlyContext = new RawContextKey<boolean>('explorerResourceReadonly', false);
 export const ExplorerResourceNotReadonlyContext = ExplorerResourceReadonlyContext.toNegated();
+/**
+ * Comma separated list of editor ids that can be used for the selected explorer resource.
+ */
+export const ExplorerResourceAvailableEditorIdsContext = new RawContextKey<string>('explorerResourceAvailableEditorIds', '');
 export const ExplorerRootContext = new RawContextKey<boolean>('explorerResourceIsRoot', false);
 export const ExplorerResourceCut = new RawContextKey<boolean>('explorerResourceCut', false);
 export const ExplorerResourceMoveableToTrash = new RawContextKey<boolean>('explorerResourceMoveableToTrash', false);
diff --git a/src/vs/workbench/contrib/files/common/openWith.ts b/src/vs/workbench/contrib/files/common/openWith.ts
new file mode 100644
index 0000000000000000000000000000000000000000..e902026eb371d702874cd61fb27a666c91180d40
--- /dev/null
+++ b/src/vs/workbench/contrib/files/common/openWith.ts
@@ -0,0 +1,138 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { basename, extname, isEqual } from 'vs/base/common/resources';
+import * as nls from 'vs/nls';
+import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
+import { IEditorOptions, ITextEditorOptions } from 'vs/platform/editor/common/editor';
+import { IQuickInputService, IQuickPickItem } from 'vs/platform/quickinput/common/quickInput';
+import { IEditorInput } from 'vs/workbench/common/editor';
+import { FileEditorInput } from 'vs/workbench/contrib/files/common/editors/fileEditorInput';
+import { DEFAULT_EDITOR_ID } from 'vs/workbench/contrib/files/common/files';
+import { CustomEditorAssociation, CustomEditorsAssociations, customEditorsAssociationsSettingId } from 'vs/workbench/services/editor/common/editorAssociationsSetting';
+import { IEditorGroup } from 'vs/workbench/services/editor/common/editorGroupsService';
+import { IEditorService, IOpenEditorOverrideHandler } from 'vs/workbench/services/editor/common/editorService';
+
+const builtinProviderDisplayName = nls.localize('builtinProviderDisplayName', "Built-in");
+
+/**
+ * Try to open an resource with a given editor.
+ *
+ * @param input Resource to open.
+ * @param id Id of the editor to use. If not provided, the user is prompted for which editor to use.
+ */
+export async function openEditorWith(
+	input: IEditorInput,
+	id: string | undefined,
+	options: IEditorOptions | ITextEditorOptions | undefined,
+	group: IEditorGroup,
+	editorService: IEditorService,
+	configurationService: IConfigurationService,
+	quickInputService: IQuickInputService,
+): Promise<void> {
+	const resource = input.resource;
+	if (!resource) {
+		return;
+	}
+
+	const resourceExt = extname(resource);
+	const overrides = editorService.getEditorOverrides(input, options, group);
+
+	const overrideToUse = overrides.find(([_, entry]) => entry.id === id);
+	if (overrideToUse) {
+		overrideToUse[0].open(input, options, group, id);
+		return;
+	}
+
+	// Prompt
+	const items: (IQuickPickItem & { handler?: IOpenEditorOverrideHandler })[] = overrides.map((override) => {
+		return {
+			handler: override[0],
+			id: override[1].id,
+			label: override[1].label,
+			description: override[1].active ? nls.localize('promptOpenWith.currentlyActive', 'Currently Active') : undefined,
+			detail: override[1].detail,
+			buttons: resourceExt ? [{
+				iconClass: 'codicon-settings-gear',
+				tooltip: nls.localize('promptOpenWith.setDefaultTooltip', "Set as default editor for '{0}' files", resourceExt)
+			}] : undefined
+		};
+	});
+
+	if (!items.length) {
+		return;
+	}
+
+	if (!items.find(item => item.id === DEFAULT_EDITOR_ID)) {
+		items.unshift({
+			id: DEFAULT_EDITOR_ID,
+			label: nls.localize('promptOpenWith.defaultEditor.displayName', "Text Editor"),
+			description: editorService.activeEditor instanceof FileEditorInput && isEqual(editorService.activeEditor.resource, resource) ? nls.localize('promptOpenWith.currentlyActive', 'Currently Active') : undefined,
+			detail: builtinProviderDisplayName,
+			buttons: resourceExt ? [{
+				iconClass: 'codicon-settings-gear',
+				tooltip: nls.localize('promptOpenWith.setDefaultTooltip', "Set as default editor for '{0}' files", resourceExt)
+			}] : undefined
+		});
+	}
+
+	const picker = quickInputService.createQuickPick<(IQuickPickItem & { handler?: IOpenEditorOverrideHandler })>();
+	picker.items = items;
+	if (items.length) {
+		picker.selectedItems = [items[0]];
+	}
+	picker.placeholder = nls.localize('promptOpenWith.placeHolder', "Select editor for '{0}'", basename(resource));
+
+	const pickedItem = await new Promise<(IQuickPickItem & { handler?: IOpenEditorOverrideHandler }) | undefined>(resolve => {
+		picker.onDidAccept(() => {
+			resolve(picker.selectedItems.length === 1 ? picker.selectedItems[0] : undefined);
+			picker.dispose();
+		});
+
+		picker.onDidTriggerItemButton(e => {
+			const pick = e.item;
+			const id = pick.id;
+			resolve(pick); // open the view
+			picker.dispose();
+
+			// And persist the setting
+			if (pick && id) {
+				const newAssociation: CustomEditorAssociation = { viewType: id, filenamePattern: '*' + resourceExt };
+				const currentAssociations = [...configurationService.getValue<CustomEditorsAssociations>(customEditorsAssociationsSettingId)];
+
+				// First try updating existing association
+				for (let i = 0; i < currentAssociations.length; ++i) {
+					const existing = currentAssociations[i];
+					if (existing.filenamePattern === newAssociation.filenamePattern) {
+						currentAssociations.splice(i, 1, newAssociation);
+						configurationService.updateValue(customEditorsAssociationsSettingId, currentAssociations);
+						return;
+					}
+				}
+
+				// Otherwise, create a new one
+				currentAssociations.unshift(newAssociation);
+				configurationService.updateValue(customEditorsAssociationsSettingId, currentAssociations);
+			}
+		});
+
+		picker.show();
+	});
+
+	if (!pickedItem) {
+		return;
+	}
+
+	if (pickedItem.id === DEFAULT_EDITOR_ID) {
+		const fileEditorInput = editorService.createEditorInput({ resource: resource!, forceFile: true });
+		const textOptions = options ? { ...options, ignoreOverrides: true } : { ignoreOverrides: true };
+
+		await editorService.openEditor(fileEditorInput, textOptions, group);
+		return;
+	}
+
+	pickedItem.handler!.open(input!, options, group, pickedItem.id);
+	return;
+}
diff --git a/src/vs/workbench/services/editor/browser/editorService.ts b/src/vs/workbench/services/editor/browser/editorService.ts
index 5c0f956cbc1135e245e6ec91cbd8d302d06a8744..02376c6f3bc533f5f9ddce9148afa6b68511fe89 100644
--- a/src/vs/workbench/services/editor/browser/editorService.ts
+++ b/src/vs/workbench/services/editor/browser/editorService.ts
@@ -34,7 +34,7 @@ import { UntitledTextEditorInput } from 'vs/workbench/services/untitled/common/u
 import { timeout } from 'vs/base/common/async';
 import { IWorkspaceContextService } from 'vs/platform/workspace/common/workspace';
 import { indexOfPath } from 'vs/base/common/extpath';
-import { DEFAULT_CUSTOM_EDITOR, updateViewTypeSchema, editorAssociationsConfigurationNode } from 'vs/workbench/services/editor/browser/editorAssociationsSetting';
+import { DEFAULT_CUSTOM_EDITOR, updateViewTypeSchema, editorAssociationsConfigurationNode } from 'vs/workbench/services/editor/common/editorAssociationsSetting';
 import { Extensions as ConfigurationExtensions, IConfigurationRegistry } from 'vs/platform/configuration/common/configurationRegistry';
 
 type CachedEditorInput = ResourceEditorInput | IFileEditorInput | UntitledTextEditorInput;
@@ -1166,7 +1166,7 @@ export class DelegatingEditorService implements IEditorService {
 	) { }
 
 	getEditorOverrides(editorInput: IEditorInput, options: IEditorOptions | undefined, group: IEditorGroup | undefined) {
-		return [];
+		return this.editorService.getEditorOverrides(editorInput, options, group);
 	}
 
 	openEditor(editor: IEditorInput, options?: IEditorOptions | ITextEditorOptions, group?: OpenInEditorGroup): Promise<IEditorPane | undefined>;
diff --git a/src/vs/workbench/services/editor/browser/editorAssociationsSetting.ts b/src/vs/workbench/services/editor/common/editorAssociationsSetting.ts
similarity index 100%
rename from src/vs/workbench/services/editor/browser/editorAssociationsSetting.ts
rename to src/vs/workbench/services/editor/common/editorAssociationsSetting.ts