diff --git a/i18n/en.json b/i18n/en.json
index cf4a77d15ed..f5e04084602 100644
--- a/i18n/en.json
+++ b/i18n/en.json
@@ -128,8 +128,6 @@
   "main.tray.tray.expired": "Session Expired: Please sign in to continue receiving notifications.",
   "main.tray.tray.mention": "You have been mentioned",
   "main.tray.tray.unread": "You have unread channels",
-  "main.views.viewManager.handleDeepLink.error.body": "There is no configured server in the app that matches the requested url: {url}",
-  "main.views.viewManager.handleDeepLink.error.title": "No matching server",
   "main.windows.mainWindow.closeApp.dialog.checkboxLabel": "Don't ask again",
   "main.windows.mainWindow.closeApp.dialog.detail": "You will no longer receive notifications for messages. If you want to leave {appName} running in the system tray, you can enable this in Settings.",
   "main.windows.mainWindow.closeApp.dialog.message": "Are you sure you want to quit?",
diff --git a/src/app/serverViewState.test.js b/src/app/serverViewState.test.js
index c5b11befe7a..4ae40b31dc9 100644
--- a/src/app/serverViewState.test.js
+++ b/src/app/serverViewState.test.js
@@ -209,7 +209,7 @@ describe('app/serverViewState', () => {
             serverViewState.showNewServerModal();
             await promise;
 
-            expect(ServerManager.addServer).toHaveBeenCalledWith(data);
+            expect(ServerManager.addServer).toHaveBeenCalledWith(data, undefined);
             expect(serversCopy).toContainEqual(expect.objectContaining({
                 id: 'server-1',
                 name: 'new-server',
diff --git a/src/app/serverViewState.ts b/src/app/serverViewState.ts
index 658f086fa70..e41ca85146e 100644
--- a/src/app/serverViewState.ts
+++ b/src/app/serverViewState.ts
@@ -44,7 +44,7 @@ export class ServerViewState {
 
     constructor() {
         ipcMain.on(SWITCH_SERVER, (event, serverId) => this.switchServer(serverId));
-        ipcMain.on(SHOW_NEW_SERVER_MODAL, this.showNewServerModal);
+        ipcMain.on(SHOW_NEW_SERVER_MODAL, this.handleShowNewServerModal);
         ipcMain.on(SHOW_EDIT_SERVER_MODAL, this.showEditServerModal);
         ipcMain.on(SHOW_REMOVE_SERVER_MODAL, this.showRemoveServerModal);
         ipcMain.handle(VALIDATE_SERVER_URL, this.handleServerURLValidation);
@@ -123,25 +123,32 @@ export class ServerViewState {
      * Server Modals
      */
 
-    showNewServerModal = () => {
-        log.debug('showNewServerModal');
+    showNewServerModal = (prefillURL?: string) => {
+        log.debug('showNewServerModal', {prefillURL});
 
         const mainWindow = MainWindow.get();
         if (!mainWindow) {
             return;
         }
 
-        const modalPromise = ModalManager.addModal<null, Server>(
+        const modalPromise = ModalManager.addModal<{prefillURL?: string}, Server>(
             'newServer',
             'mattermost-desktop://renderer/newServer.html',
             getLocalPreload('internalAPI.js'),
-            null,
+            {prefillURL},
             mainWindow,
             !ServerManager.hasServers(),
         );
 
         modalPromise.then((data) => {
-            const newServer = ServerManager.addServer(data);
+            let initialLoadURL;
+            if (prefillURL) {
+                const parsedServerURL = parseURL(data.url);
+                if (parsedServerURL) {
+                    initialLoadURL = parseURL(`${parsedServerURL.origin}${prefillURL.substring(prefillURL.indexOf('/'))}`);
+                }
+            }
+            const newServer = ServerManager.addServer(data, initialLoadURL);
             this.switchServer(newServer.id, true);
         }).catch((e) => {
             // e is undefined for user cancellation
@@ -151,6 +158,8 @@ export class ServerViewState {
         });
     };
 
+    private handleShowNewServerModal = () => this.showNewServerModal();
+
     private showEditServerModal = (e: IpcMainEvent, id: string) => {
         log.debug('showEditServerModal', id);
 
@@ -281,6 +290,11 @@ export class ServerViewState {
         // If the original URL was invalid, don't replace that as they probably have a typo somewhere
         // Also strip the trailing slash if it's there so that the user can keep typing
         if (!remoteInfo) {
+            // If the URL provided has a path, try to validate the server with parts of the path removed, until we reach the root and then return a failure
+            if (parsedURL.pathname !== '/') {
+                return this.handleServerURLValidation(e, parsedURL.toString().substring(0, parsedURL.toString().lastIndexOf('/')), currentId);
+            }
+
             return {status: URLValidationStatus.NotMattermost, validatedURL: parsedURL.toString().replace(/\/$/, '')};
         }
 
diff --git a/src/common/servers/MattermostServer.ts b/src/common/servers/MattermostServer.ts
index d98c7a14d67..5210838798c 100644
--- a/src/common/servers/MattermostServer.ts
+++ b/src/common/servers/MattermostServer.ts
@@ -12,14 +12,16 @@ export class MattermostServer {
     name: string;
     url!: URL;
     isPredefined: boolean;
+    initialLoadURL?: URL;
 
-    constructor(server: Server, isPredefined: boolean) {
+    constructor(server: Server, isPredefined: boolean, initialLoadURL?: URL) {
         this.id = uuid();
 
         this.name = server.name;
         this.updateURL(server.url);
 
         this.isPredefined = isPredefined;
+        this.initialLoadURL = initialLoadURL;
     }
 
     updateURL = (url: string) => {
diff --git a/src/common/servers/serverManager.ts b/src/common/servers/serverManager.ts
index d2edd1e6696..fad1a67c578 100644
--- a/src/common/servers/serverManager.ts
+++ b/src/common/servers/serverManager.ts
@@ -156,8 +156,8 @@ export class ServerManager extends EventEmitter {
         this.persistServers();
     };
 
-    addServer = (server: Server) => {
-        const newServer = new MattermostServer(server, false);
+    addServer = (server: Server, initialLoadURL?: URL) => {
+        const newServer = new MattermostServer(server, false, initialLoadURL);
 
         if (this.servers.has(newServer.id)) {
             throw new Error('ID Collision detected. Cannot add server.');
diff --git a/src/main/app/intercom.test.js b/src/main/app/intercom.test.js
index c186a1fa37b..e7443f97457 100644
--- a/src/main/app/intercom.test.js
+++ b/src/main/app/intercom.test.js
@@ -63,7 +63,7 @@ describe('main/app/intercom', () => {
             ModalManager.addModal.mockReturnValue(promise);
 
             handleWelcomeScreenModal();
-            expect(ModalManager.addModal).toHaveBeenCalledWith('welcomeScreen', 'mattermost-desktop://renderer/welcomeScreen.html', '/some/preload.js', null, {}, true);
+            expect(ModalManager.addModal).toHaveBeenCalledWith('welcomeScreen', 'mattermost-desktop://renderer/welcomeScreen.html', '/some/preload.js', {prefillURL: undefined}, {}, true);
         });
     });
 
diff --git a/src/main/app/intercom.ts b/src/main/app/intercom.ts
index 8acfac87d8e..41c4dfb1b10 100644
--- a/src/main/app/intercom.ts
+++ b/src/main/app/intercom.ts
@@ -8,6 +8,7 @@ import ServerViewState from 'app/serverViewState';
 import {Logger} from 'common/log';
 import ServerManager from 'common/servers/serverManager';
 import {ping} from 'common/utils/requests';
+import {parseURL} from 'common/utils/url';
 import NotificationManager from 'main/notifications';
 import {getLocalPreload} from 'main/utils';
 import ModalManager from 'main/views/modalManager';
@@ -85,7 +86,7 @@ export function handleMainWindowIsShown() {
     }
 }
 
-export function handleWelcomeScreenModal() {
+export function handleWelcomeScreenModal(prefillURL?: string) {
     log.debug('handleWelcomeScreenModal');
 
     const html = 'mattermost-desktop://renderer/welcomeScreen.html';
@@ -96,10 +97,17 @@ export function handleWelcomeScreenModal() {
     if (!mainWindow) {
         return;
     }
-    const modalPromise = ModalManager.addModal<null, UniqueServer>('welcomeScreen', html, preload, null, mainWindow, !ServerManager.hasServers());
+    const modalPromise = ModalManager.addModal<{prefillURL?: string}, UniqueServer>('welcomeScreen', html, preload, {prefillURL}, mainWindow, !ServerManager.hasServers());
     if (modalPromise) {
         modalPromise.then((data) => {
-            const newServer = ServerManager.addServer(data);
+            let initialLoadURL;
+            if (prefillURL) {
+                const parsedServerURL = parseURL(data.url);
+                if (parsedServerURL) {
+                    initialLoadURL = parseURL(`${parsedServerURL.origin}${prefillURL.substring(prefillURL.indexOf('/'))}`);
+                }
+            }
+            const newServer = ServerManager.addServer(data, initialLoadURL);
             ServerViewState.switchServer(newServer.id, true);
         }).catch((e) => {
             // e is undefined for user cancellation
diff --git a/src/main/views/modalManager.ts b/src/main/views/modalManager.ts
index 590fe25da46..b496deaac52 100644
--- a/src/main/views/modalManager.ts
+++ b/src/main/views/modalManager.ts
@@ -65,6 +65,18 @@ export class ModalManager {
         return this.modalPromises.get(key) as Promise<T2>;
     };
 
+    removeModal = (key: string) => {
+        const modalView = this.modalQueue.find((modal) => modal.key === key);
+        if (!modalView) {
+            return;
+        }
+
+        modalView.hide();
+        modalView.resolve(null);
+        this.modalPromises.delete(key);
+        this.filterActive();
+    };
+
     findModalByCaller = (event: IpcMainInvokeEvent) => {
         if (this.modalQueue.length) {
             const requestModal = this.modalQueue.find((modal) => {
diff --git a/src/main/views/viewManager.test.js b/src/main/views/viewManager.test.js
index 0075041900a..668c0e8bb38 100644
--- a/src/main/views/viewManager.test.js
+++ b/src/main/views/viewManager.test.js
@@ -1,8 +1,6 @@
 // Copyright (c) 2016-present Mattermost, Inc. All Rights Reserved.
 // See LICENSE.txt for license information.
 
-import {dialog} from 'electron';
-
 import ServerViewState from 'app/serverViewState';
 import {BROWSER_HISTORY_PUSH, LOAD_SUCCESS, SET_ACTIVE_VIEW} from 'common/communication';
 import ServerManager from 'common/servers/serverManager';
@@ -20,9 +18,6 @@ jest.mock('electron', () => ({
         getAppPath: () => '/path/to/app',
         getPath: jest.fn(() => '/valid/downloads/path'),
     },
-    dialog: {
-        showErrorBox: jest.fn(),
-    },
     ipcMain: {
         emit: jest.fn(),
         on: jest.fn(),
@@ -33,6 +28,7 @@ jest.mock('app/serverViewState', () => ({
     getCurrentServer: jest.fn(),
     updateCurrentView: jest.fn(),
     init: jest.fn(),
+    showNewServerModal: jest.fn(),
 }));
 jest.mock('common/views/View', () => ({
     getViewName: jest.fn((a, b) => `${a}-${b}`),
@@ -62,6 +58,10 @@ jest.mock('main/app/utils', () => ({
     flushCookiesStore: jest.fn(),
 }));
 
+jest.mock('main/app/intercom', () => ({
+    handleWelcomeScreenModal: jest.fn(),
+}));
+
 jest.mock('main/i18nManager', () => ({
     localizeMessage: jest.fn(),
 }));
@@ -116,8 +116,9 @@ jest.mock('./MattermostWebContentsView', () => ({
     MattermostWebContentsView: jest.fn(),
 }));
 
-jest.mock('./modalManager', () => ({
+jest.mock('main/views/modalManager', () => ({
     showModal: jest.fn(),
+    removeModal: jest.fn(),
     isModalDisplayed: jest.fn(),
 }));
 jest.mock('./webContentEvents', () => ({}));
@@ -321,6 +322,7 @@ describe('main/views/viewManager', () => {
                     isOpen: true,
                     url: new URL('http://server1.com/view'),
                 },
+                undefined,
             );
             makeSpy.mockRestore();
         });
@@ -692,11 +694,12 @@ describe('main/views/viewManager', () => {
             expect(view.load).not.toHaveBeenCalled();
         });
 
-        it('should throw dialog when cannot find the view', () => {
+        it('should open new server modal when using a server that does not exist', () => {
+            ServerManager.hasServers.mockReturnValue(true);
             const view = {...baseView};
-            viewManager.handleDeepLink('mattermost://server-1.com/deep/link?thing=yes');
+            viewManager.handleDeepLink('mattermost://server-2.com/deep/link?thing=yes');
             expect(view.load).not.toHaveBeenCalled();
-            expect(dialog.showErrorBox).toHaveBeenCalled();
+            expect(ServerViewState.showNewServerModal).toHaveBeenCalled();
         });
 
         it('should reopen closed view if called upon', () => {
diff --git a/src/main/views/viewManager.ts b/src/main/views/viewManager.ts
index 3de2c1596c2..0eae96890df 100644
--- a/src/main/views/viewManager.ts
+++ b/src/main/views/viewManager.ts
@@ -2,7 +2,7 @@
 // See LICENSE.txt for license information.
 
 import type {IpcMainEvent, IpcMainInvokeEvent} from 'electron';
-import {WebContentsView, dialog, ipcMain} from 'electron';
+import {WebContentsView, ipcMain} from 'electron';
 import isDev from 'electron-is-dev';
 
 import ServerViewState from 'app/serverViewState';
@@ -41,18 +41,18 @@ import {getFormattedPathName, parseURL} from 'common/utils/url';
 import Utils from 'common/utils/util';
 import type {MattermostView} from 'common/views/View';
 import {TAB_MESSAGING} from 'common/views/View';
+import {handleWelcomeScreenModal} from 'main/app/intercom';
 import {flushCookiesStore} from 'main/app/utils';
 import DeveloperMode from 'main/developerMode';
-import {localizeMessage} from 'main/i18nManager';
 import performanceMonitor from 'main/performanceMonitor';
 import PermissionsManager from 'main/permissionsManager';
+import ModalManager from 'main/views/modalManager';
 import MainWindow from 'main/windows/mainWindow';
 
 import type {DeveloperSettings} from 'types/settings';
 
 import LoadingScreen from './loadingScreen';
 import {MattermostWebContentsView} from './MattermostWebContentsView';
-import modalManager from './modalManager';
 
 import {getLocalPreload, getAdjustedWindowBoundaries} from '../utils';
 
@@ -158,14 +158,14 @@ export class ViewManager {
         } else {
             this.getViewLogger(viewId).warn(`Couldn't find a view with name: ${viewId}`);
         }
-        modalManager.showModal();
+        ModalManager.showModal();
     };
 
     focusCurrentView = () => {
         log.debug('focusCurrentView');
 
-        if (modalManager.isModalDisplayed()) {
-            modalManager.focusCurrentModal();
+        if (ModalManager.isModalDisplayed()) {
+            ModalManager.focusCurrentModal();
             return;
         }
 
@@ -227,11 +227,11 @@ export class ViewManager {
                         webContentsView.once(LOAD_FAILED, this.deeplinkFailed);
                     }
                 }
+            } else if (ServerManager.hasServers()) {
+                ServerViewState.showNewServerModal(`${parsedURL.host}${getFormattedPathName(parsedURL.pathname)}${parsedURL.search}`);
             } else {
-                dialog.showErrorBox(
-                    localizeMessage('main.views.viewManager.handleDeepLink.error.title', 'No matching server'),
-                    localizeMessage('main.views.viewManager.handleDeepLink.error.body', 'There is no configured server in the app that matches the requested url: {url}', {url: parsedURL.toString()}),
-                );
+                ModalManager.removeModal('welcomeScreen');
+                handleWelcomeScreenModal(`${parsedURL.host}${getFormattedPathName(parsedURL.pathname)}${parsedURL.search}`);
             }
         }
     };
@@ -439,7 +439,7 @@ export class ViewManager {
             } else if (recycle) {
                 views.set(view.id, recycle);
             } else {
-                views.set(view.id, this.makeView(srv, view));
+                views.set(view.id, this.makeView(srv, view, srv.initialLoadURL?.toString()));
             }
         }
 
diff --git a/src/renderer/components/ConfigureServer.tsx b/src/renderer/components/ConfigureServer.tsx
index a76cfa2eb96..86b239dd893 100644
--- a/src/renderer/components/ConfigureServer.tsx
+++ b/src/renderer/components/ConfigureServer.tsx
@@ -20,6 +20,7 @@ import 'renderer/css/components/LoadingScreen.css';
 
 type ConfigureServerProps = {
     server?: UniqueServer;
+    prefillURL?: string;
     mobileView?: boolean;
     darkMode?: boolean;
     messageTitle?: string;
@@ -33,6 +34,7 @@ type ConfigureServerProps = {
 
 function ConfigureServer({
     server,
+    prefillURL,
     mobileView,
     darkMode,
     messageTitle,
@@ -53,8 +55,8 @@ function ConfigureServer({
 
     const mounted = useRef(false);
     const [transition, setTransition] = useState<'inFromRight' | 'outToLeft'>();
-    const [name, setName] = useState(prevName || '');
-    const [url, setUrl] = useState(prevURL || '');
+    const [name, setName] = useState(prevName ?? '');
+    const [url, setUrl] = useState(prevURL ?? prefillURL ?? '');
     const [nameError, setNameError] = useState('');
     const [urlError, setURLError] = useState<{type: STATUS; value: string}>();
     const [showContent, setShowContent] = useState(false);
@@ -71,6 +73,11 @@ function ConfigureServer({
         setTransition('inFromRight');
         setShowContent(true);
         mounted.current = true;
+
+        if (url) {
+            fetchValidationResult(url);
+        }
+
         return () => {
             mounted.current = false;
         };
diff --git a/src/renderer/components/NewServerModal.tsx b/src/renderer/components/NewServerModal.tsx
index d39e6e4d347..3a6c28b32ef 100644
--- a/src/renderer/components/NewServerModal.tsx
+++ b/src/renderer/components/NewServerModal.tsx
@@ -27,6 +27,7 @@ type Props = {
     currentOrder?: number;
     setInputRef?: (inputRef: HTMLInputElement) => void;
     intl: IntlShape;
+    prefillURL?: string;
 };
 
 type State = {
@@ -77,6 +78,13 @@ class NewServerModal extends React.PureComponent<Props, State> {
         this.mounted = false;
     }
 
+    componentDidUpdate(prevProps: Readonly<Props>): void {
+        if (this.props.prefillURL && this.props.prefillURL !== prevProps.prefillURL) {
+            this.setState({serverUrl: this.props.prefillURL});
+            this.validateServerURL(this.props.prefillURL);
+        }
+    }
+
     initializeOnShow = async () => {
         const cameraDisabled = window.process.platform === 'win32' && await window.desktop.getMediaAccessStatus('camera') !== 'granted';
         const microphoneDisabled = window.process.platform === 'win32' && await window.desktop.getMediaAccessStatus('microphone') !== 'granted';
diff --git a/src/renderer/modals/newServer/newServer.tsx b/src/renderer/modals/newServer/newServer.tsx
index da1452b1798..4f08655448a 100644
--- a/src/renderer/modals/newServer/newServer.tsx
+++ b/src/renderer/modals/newServer/newServer.tsx
@@ -25,12 +25,18 @@ const onSave = (data: UniqueServer) => {
 };
 
 const NewServerModalWrapper: React.FC = () => {
+    const [data, setData] = useState<{prefillURL?: string}>();
     const [unremoveable, setUnremovable] = useState<boolean>();
 
     useEffect(() => {
         window.desktop.modals.isModalUncloseable().then((uncloseable) => {
             setUnremovable(uncloseable);
         });
+
+        window.desktop.modals.getModalInfo<{prefillURL?: string}>().
+            then((data) => {
+                setData(data);
+            });
     }, []);
 
     return (
@@ -39,6 +45,7 @@ const NewServerModalWrapper: React.FC = () => {
                 onClose={unremoveable ? undefined : onClose}
                 onSave={onSave}
                 editMode={false}
+                prefillURL={data?.prefillURL}
                 show={true}
             />
         </IntlProvider>
diff --git a/src/renderer/modals/welcomeScreen/welcomeScreen.tsx b/src/renderer/modals/welcomeScreen/welcomeScreen.tsx
index b633914d653..962fbd35fb5 100644
--- a/src/renderer/modals/welcomeScreen/welcomeScreen.tsx
+++ b/src/renderer/modals/welcomeScreen/welcomeScreen.tsx
@@ -20,6 +20,7 @@ const onConnect = (data: UniqueServer) => {
 };
 
 const WelcomeScreenModalWrapper = () => {
+    const [data, setData] = useState<{prefillURL?: string}>();
     const [darkMode, setDarkMode] = useState(false);
     const [getStarted, setGetStarted] = useState(false);
     const [mobileView, setMobileView] = useState(false);
@@ -37,6 +38,14 @@ const WelcomeScreenModalWrapper = () => {
             setDarkMode(result);
         });
 
+        window.desktop.modals.getModalInfo<{prefillURL?: string}>().
+            then((data) => {
+                setData(data);
+                if (data.prefillURL) {
+                    setGetStarted(true);
+                }
+            });
+
         handleWindowResize();
         window.addEventListener('resize', handleWindowResize);
 
@@ -56,6 +65,7 @@ const WelcomeScreenModalWrapper = () => {
                     mobileView={mobileView}
                     darkMode={darkMode}
                     onConnect={onConnect}
+                    prefillURL={data?.prefillURL}
                 />
             ) : (
                 <WelcomeScreen