diff --git a/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.story.tsx b/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.story.tsx
index 7b697092f7c62..1ffe93e4cb080 100644
--- a/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.story.tsx
+++ b/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.story.tsx
@@ -16,6 +16,7 @@
  * along with this program.  If not, see <http://www.gnu.org/licenses/>.
  */
 
+import { Meta } from '@storybook/react';
 import { wait } from 'shared/utils/wait';
 
 import { MockAppContextProvider } from 'teleterm/ui/fixtures/MockAppContextProvider';
@@ -33,39 +34,41 @@ import { DocumentAuthorizeWebSession } from './DocumentAuthorizeWebSession';
 
 export default {
   title: 'Teleterm/DocumentAuthorizeWebSession',
-};
-
-const doc: types.DocumentAuthorizeWebSession = {
-  uri: '/docs/e2hyt5',
-  rootClusterUri: rootClusterUri,
-  kind: 'doc.authorize_web_session',
-  title: 'Authorize Web Session',
-  webSessionRequest: {
-    redirectUri: '',
-    token: '',
-    id: '',
+  component: Story,
+  argTypes: {
+    isDeviceTrusted: { control: { type: 'boolean' } },
+    isRequestedUserLoggedIn: { control: { type: 'boolean' } },
+  },
+  args: {
+    isDeviceTrusted: true,
+    isRequestedUserLoggedIn: true,
   },
-};
+} satisfies Meta<StoryProps>;
 
-export function DeviceNotTrusted() {
-  const rootCluster = makeRootCluster();
-  const appContext = new MockAppContext();
-  appContext.clustersService.setState(draftState => {
-    draftState.clusters.set(rootCluster.uri, rootCluster);
-  });
-  return (
-    <MockAppContextProvider appContext={appContext}>
-      <MockWorkspaceContextProvider rootClusterUri={rootCluster.uri}>
-        <DocumentAuthorizeWebSession doc={doc} visible={true} />
-      </MockWorkspaceContextProvider>
-    </MockAppContextProvider>
-  );
+interface StoryProps {
+  isDeviceTrusted: boolean;
+  isRequestedUserLoggedIn: boolean;
 }
 
-export function DeviceTrusted() {
+export function Story(props: StoryProps) {
   const rootCluster = makeRootCluster({
-    loggedInUser: makeLoggedInUser({ isDeviceTrusted: true }),
+    loggedInUser: makeLoggedInUser({ isDeviceTrusted: props.isDeviceTrusted }),
   });
+  const doc: types.DocumentAuthorizeWebSession = {
+    uri: '/docs/e2hyt5',
+    rootClusterUri: rootClusterUri,
+    kind: 'doc.authorize_web_session',
+    title: 'Authorize Web Session',
+    webSessionRequest: {
+      redirectUri: '',
+      token: '',
+      id: '',
+      username: props.isRequestedUserLoggedIn
+        ? rootCluster.loggedInUser.name
+        : 'bob',
+    },
+  };
+
   const appContext = new MockAppContext();
   appContext.clustersService.setState(draftState => {
     draftState.clusters.set(rootCluster.uri, rootCluster);
diff --git a/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.test.tsx b/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.test.tsx
index c06ff109ff93c..67f47026cde36 100644
--- a/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.test.tsx
+++ b/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.test.tsx
@@ -40,10 +40,11 @@ const doc: types.DocumentAuthorizeWebSession = {
     redirectUri: '',
     token: '',
     id: '',
+    username: 'alice',
   },
 };
 
-test('authorize button is disabled when device is not trusted', async () => {
+test('warning is visible and authorize button is disabled when device is not trusted', async () => {
   const rootCluster = makeRootCluster({
     loggedInUser: makeLoggedInUser({ isDeviceTrusted: false }),
   });
@@ -64,6 +65,29 @@ test('authorize button is disabled when device is not trusted', async () => {
   expect(await screen.findByText(/Authorize Session/)).toBeDisabled();
 });
 
+test('warning is visible and authorize button is disabled when requested user is not logged in', async () => {
+  const rootCluster = makeRootCluster({
+    loggedInUser: makeLoggedInUser({ isDeviceTrusted: true, name: 'bob' }),
+  });
+  const appContext = new MockAppContext();
+  appContext.clustersService.setState(draftState => {
+    draftState.clusters.set(rootCluster.uri, rootCluster);
+  });
+
+  render(
+    <MockAppContextProvider appContext={appContext}>
+      <MockWorkspaceContextProvider rootClusterUri={rootCluster.uri}>
+        <DocumentAuthorizeWebSession doc={doc} visible={true} />
+      </MockWorkspaceContextProvider>
+    </MockAppContextProvider>
+  );
+
+  expect(
+    await screen.findByText(/Requested user is not logged in/)
+  ).toBeVisible();
+  expect(await screen.findByText(/Authorize Session/)).toBeDisabled();
+});
+
 test('authorizing a session opens its URL and closes document', async () => {
   jest.spyOn(window, 'open').mockImplementation();
   const rootCluster = makeRootCluster({
diff --git a/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.tsx b/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.tsx
index 461a8de679ae4..18ff95e499575 100644
--- a/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.tsx
+++ b/web/packages/teleterm/src/ui/DocumentAuthorizeWebSession/DocumentAuthorizeWebSession.tsx
@@ -50,7 +50,10 @@ export function DocumentAuthorizeWebSession(props: {
     return confirmationToken;
   });
   const clusterName = routing.parseClusterName(props.doc.rootClusterUri);
-  const canAuthorize = rootCluster.loggedInUser?.isDeviceTrusted;
+  const isDeviceTrusted = rootCluster.loggedInUser?.isDeviceTrusted;
+  const isRequestedUserLoggedIn =
+    props.doc.webSessionRequest.username === rootCluster.loggedInUser?.name;
+  const canAuthorize = isDeviceTrusted && isRequestedUserLoggedIn;
 
   async function authorizeAndCloseDocument() {
     const [confirmationToken, error] = await authorize();
@@ -95,7 +98,7 @@ export function DocumentAuthorizeWebSession(props: {
         <H1 mb="4">Authorize Web Session</H1>
         <Flex flexDirection="column" gap={3}>
           {/*It's technically possible to open a deep link to authorize a session on a device that is not enrolled.*/}
-          {!canAuthorize && (
+          {!isDeviceTrusted && (
             <Alert
               mb={0}
               details={
@@ -115,6 +118,31 @@ export function DocumentAuthorizeWebSession(props: {
               This device is not trusted
             </Alert>
           )}
+          {!isRequestedUserLoggedIn && (
+            <Alert
+              mb={0}
+              primaryAction={{
+                content: 'Log Out',
+                onClick: () => {
+                  ctx.commandLauncher.executeCommand('cluster-logout', {
+                    clusterUri: rootCluster.uri,
+                  });
+                },
+              }}
+              details={
+                <>
+                  You are logged in as <b>{rootCluster.loggedInUser?.name}</b>.
+                  To authorize this web session request, please log out in
+                  Teleport Connect and log in again as{' '}
+                  <b>{props.doc.webSessionRequest.username}</b>.
+                  <br />
+                  Then click Launch Teleport Connect again in the browser.
+                </>
+              }
+            >
+              Requested user is not logged in
+            </Alert>
+          )}
           {authorizeAttempt.status === 'error' && (
             <Alert mb={0} details={authorizeAttempt.statusText}>
               Could not authorize the session
diff --git a/web/packages/teleterm/src/ui/services/deepLinks/deepLinksService.ts b/web/packages/teleterm/src/ui/services/deepLinks/deepLinksService.ts
index 6083df679f626..ea98c9a51ef40 100644
--- a/web/packages/teleterm/src/ui/services/deepLinks/deepLinksService.ts
+++ b/web/packages/teleterm/src/ui/services/deepLinks/deepLinksService.ts
@@ -117,6 +117,7 @@ export class DeepLinksService {
       webSessionRequest: {
         id,
         token,
+        username: url.username,
         redirectUri: redirect_uri,
       },
     });
diff --git a/web/packages/teleterm/src/ui/services/workspacesService/documentsService/types.ts b/web/packages/teleterm/src/ui/services/workspacesService/documentsService/types.ts
index 0c7fd36952285..00238ae5b35fd 100644
--- a/web/packages/teleterm/src/ui/services/workspacesService/documentsService/types.ts
+++ b/web/packages/teleterm/src/ui/services/workspacesService/documentsService/types.ts
@@ -237,6 +237,7 @@ export interface DocumentAuthorizeWebSession extends DocumentBase {
 export interface WebSessionRequest {
   id: string;
   token: string;
+  username: string;
   redirectUri: string;
 }
 
diff --git a/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts b/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts
index ded2d08080df5..ccb1add834217 100644
--- a/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts
+++ b/web/packages/teleterm/src/ui/services/workspacesService/workspacesService.test.ts
@@ -218,6 +218,7 @@ describe('state persistence', () => {
                 id: '',
                 token: '',
                 redirectUri: '',
+                username: '',
               },
             },
           ],