diff --git a/site/src/components/Dialogs/Dialog.tsx b/site/src/components/Dialogs/Dialog.tsx
index 7f249c74c590b..9ca0b36f9c352 100644
--- a/site/src/components/Dialogs/Dialog.tsx
+++ b/site/src/components/Dialogs/Dialog.tsx
@@ -65,6 +65,7 @@ export const DialogActionButtons: React.FC<DialogActionButtonsProps> = ({
       {onConfirm && (
         <LoadingButton
           fullWidth
+          data-testid="confirm-button"
           variant="contained"
           onClick={onConfirm}
           color={typeToColor(type)}
diff --git a/site/src/components/Resources/AgentRow.tsx b/site/src/components/Resources/AgentRow.tsx
index e4b458ab83a6d..2dd0bb81a24c4 100644
--- a/site/src/components/Resources/AgentRow.tsx
+++ b/site/src/components/Resources/AgentRow.tsx
@@ -114,10 +114,10 @@ export const AgentRow: FC<AgentRowProps> = ({
   useEffect(() => {
     // We only want to fetch logs when they are actually shown,
     // otherwise we can make a lot of requests that aren't necessary.
-    if (showStartupLogs) {
+    if (showStartupLogs && logsMachine.can("FETCH_STARTUP_LOGS")) {
       sendLogsEvent("FETCH_STARTUP_LOGS")
     }
-  }, [sendLogsEvent, showStartupLogs])
+  }, [logsMachine, sendLogsEvent, showStartupLogs])
   const logListRef = useRef<List>(null)
   const logListDivRef = useRef<HTMLDivElement>(null)
   const startupLogs = useMemo(() => {
diff --git a/site/src/components/WorkspaceActions/Buttons.tsx b/site/src/components/WorkspaceActions/Buttons.tsx
index d6207952a4ac8..19fc2d96a0d06 100644
--- a/site/src/components/WorkspaceActions/Buttons.tsx
+++ b/site/src/components/WorkspaceActions/Buttons.tsx
@@ -21,6 +21,7 @@ export const UpdateButton: FC<PropsWithChildren<WorkspaceAction>> = ({
 
   return (
     <Button
+      data-testid="workspace-update-button"
       variant="outlined"
       startIcon={<CloudQueueIcon />}
       onClick={handleAction}
diff --git a/site/src/pages/WorkspaceBuildPage/WorkspaceBuildPage.test.tsx b/site/src/pages/WorkspaceBuildPage/WorkspaceBuildPage.test.tsx
index 4c2512ccceff2..72a68bc6ffff4 100644
--- a/site/src/pages/WorkspaceBuildPage/WorkspaceBuildPage.test.tsx
+++ b/site/src/pages/WorkspaceBuildPage/WorkspaceBuildPage.test.tsx
@@ -1,11 +1,8 @@
 import { screen } from "@testing-library/react"
 import WS from "jest-websocket-mock"
-import {
-  MockWorkspace,
-  MockWorkspaceBuild,
-  renderWithAuth,
-} from "../../testHelpers/renderHelpers"
+import { renderWithAuth } from "../../testHelpers/renderHelpers"
 import { WorkspaceBuildPage } from "./WorkspaceBuildPage"
+import { MockWorkspace, MockWorkspaceBuild } from "testHelpers/entities"
 
 describe("WorkspaceBuildPage", () => {
   test("the mock server seamlessly handles JSON protocols", async () => {
diff --git a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
index 8739d74dfb0fb..4ca8a3910749b 100644
--- a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
+++ b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
@@ -35,6 +35,10 @@ const { t } = i18next
 const renderWorkspacePage = async () => {
   jest.spyOn(api, "getTemplate").mockResolvedValueOnce(MockTemplate)
   jest.spyOn(api, "getTemplateVersionRichParameters").mockResolvedValueOnce([])
+  jest.spyOn(api, "watchStartupLogs").mockImplementation((_, options) => {
+    options.onDone()
+    return new WebSocket("")
+  })
   renderWithAuth(<WorkspacePage />, {
     route: `/@${MockWorkspace.owner_name}/${MockWorkspace.name}`,
     path: "/@:username/:workspace",
@@ -188,22 +192,32 @@ describe("WorkspacePage", () => {
   })
 
   it("requests an update when the user presses Update", async () => {
+    // Mocks
     jest
       .spyOn(api, "getWorkspaceByOwnerAndName")
       .mockResolvedValueOnce(MockOutdatedWorkspace)
+
     const updateWorkspaceMock = jest
       .spyOn(api, "updateWorkspace")
       .mockResolvedValueOnce(MockWorkspaceBuild)
 
-    await testButton(
-      t("actionButton.update", { ns: "workspacePage" }),
-      updateWorkspaceMock,
-    )
+    // Render
+    await renderWorkspacePage()
+
+    // Actions
+    const user = userEvent.setup()
+    await user.click(screen.getByTestId("workspace-update-button"))
+    const confirmButton = await screen.findByTestId("confirm-button")
+    await user.click(confirmButton)
+
+    // Assertions
+    await waitFor(() => {
+      expect(updateWorkspaceMock).toBeCalled()
+    })
   })
 
   it("updates the parameters when they are missing during update", async () => {
-    // Setup mocks
-    const user = userEvent.setup()
+    // Mocks
     jest
       .spyOn(api, "getWorkspaceByOwnerAndName")
       .mockResolvedValueOnce(MockOutdatedWorkspace)
@@ -215,23 +229,24 @@ describe("WorkspacePage", () => {
           MockTemplateVersionParameter2,
         ]),
       )
-    // Render page and wait for it to be loaded
-    renderWithAuth(<WorkspacePage />, {
-      route: `/@${MockWorkspace.owner_name}/${MockWorkspace.name}`,
-      path: "/@:username/:workspace",
-    })
-    await waitForLoaderToBeRemoved()
-    // Click on the update button
-    const workspaceActions = screen.getByTestId("workspace-actions")
-    await user.click(
-      within(workspaceActions).getByRole("button", { name: "Update" }),
-    )
+
+    // Render
+    await renderWorkspacePage()
+
+    // Actions
+    const user = userEvent.setup()
+    await user.click(screen.getByTestId("workspace-update-button"))
+    const confirmButton = await screen.findByTestId("confirm-button")
+    await user.click(confirmButton)
+
+    // The update was called
     await waitFor(() => {
       expect(api.updateWorkspace).toBeCalled()
-      // We want to clear this mock to use it later
       updateWorkspaceSpy.mockClear()
     })
-    // Fill the parameters and send the form
+
+    // After trying to update, a new dialog asking for missed parameters should
+    // be displayed and filled
     const dialog = await screen.findByTestId("dialog")
     const firstParameterInput = within(dialog).getByLabelText(
       MockTemplateVersionParameter1.name,
@@ -246,6 +261,7 @@ describe("WorkspacePage", () => {
     await user.clear(secondParameterInput)
     await user.type(secondParameterInput, "2")
     await user.click(within(dialog).getByRole("button", { name: "Update" }))
+
     // Check if the update was called using the values from the form
     await waitFor(() => {
       expect(api.updateWorkspace).toBeCalledWith(MockOutdatedWorkspace, [
diff --git a/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx b/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
index 9b17aedeaed3f..f25ca22927a4b 100644
--- a/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
@@ -31,6 +31,7 @@ import { ChangeVersionDialog } from "./ChangeVersionDialog"
 import { useQuery } from "@tanstack/react-query"
 import { getTemplateVersions } from "api/api"
 import { useRestartWorkspace } from "./hooks"
+import { ConfirmDialog } from "components/Dialogs/ConfirmDialog/ConfirmDialog"
 
 interface WorkspaceReadyPageProps {
   workspaceState: StateFrom<typeof workspaceMachine>
@@ -76,6 +77,7 @@ export const WorkspaceReadyPage = ({
     queryFn: () => getTemplateVersions(workspace.template_id),
     enabled: changeVersionDialogOpen,
   })
+  const [isConfirmingUpdate, setIsConfirmingUpdate] = useState(false)
 
   const {
     mutate: restartWorkspace,
@@ -132,7 +134,7 @@ export const WorkspaceReadyPage = ({
         handleStop={() => workspaceSend({ type: "STOP" })}
         handleRestart={() => restartWorkspace(workspace)}
         handleDelete={() => workspaceSend({ type: "ASK_DELETE" })}
-        handleUpdate={() => workspaceSend({ type: "UPDATE" })}
+        handleUpdate={() => setIsConfirmingUpdate(true)}
         handleCancel={() => workspaceSend({ type: "CANCEL" })}
         handleSettings={() => navigate("settings")}
         handleBuildRetry={() => workspaceSend({ type: "RETRY_BUILD" })}
@@ -198,6 +200,19 @@ export const WorkspaceReadyPage = ({
           })
         }}
       />
+      <ConfirmDialog
+        type="info"
+        hideCancel={false}
+        open={isConfirmingUpdate}
+        onConfirm={() => {
+          workspaceSend({ type: "UPDATE" })
+          setIsConfirmingUpdate(false)
+        }}
+        onClose={() => setIsConfirmingUpdate(false)}
+        title="Confirm update"
+        confirmText="Update"
+        description="Are you sure you want to update your workspace? Updating your workspace will stop all running processes and delete non-persistent data."
+      />
     </>
   )
 }
diff --git a/site/src/testHelpers/entities.ts b/site/src/testHelpers/entities.ts
index 46ce3b64935ab..4f64baeae3fa8 100644
--- a/site/src/testHelpers/entities.ts
+++ b/site/src/testHelpers/entities.ts
@@ -1639,3 +1639,36 @@ export const MockDeploymentStats: TypesGen.DeploymentStats = {
     tx_bytes: 36113513253,
   },
 }
+
+export const MockDeploymentSSH: TypesGen.SSHConfigResponse = {
+  hostname_prefix: " coder.",
+  ssh_config_options: {},
+}
+
+export const MockStartupLogs: TypesGen.WorkspaceAgentStartupLog[] = [
+  {
+    id: 166663,
+    created_at: "2023-05-04T11:30:41.402072Z",
+    output: "+ curl -fsSL https://code-server.dev/install.sh",
+    level: "info",
+  },
+  {
+    id: 166664,
+    created_at: "2023-05-04T11:30:41.40228Z",
+    output:
+      "+ sh -s -- --method=standalone --prefix=/tmp/code-server --version 4.8.3",
+    level: "info",
+  },
+  {
+    id: 166665,
+    created_at: "2023-05-04T11:30:42.590731Z",
+    output: "Ubuntu 22.04.2 LTS",
+    level: "info",
+  },
+  {
+    id: 166666,
+    created_at: "2023-05-04T11:30:42.593686Z",
+    output: "Installing v4.8.3 of the amd64 release from GitHub.",
+    level: "info",
+  },
+]
diff --git a/site/src/testHelpers/handlers.ts b/site/src/testHelpers/handlers.ts
index 1cfa9e87fc3d2..c738b497253a9 100644
--- a/site/src/testHelpers/handlers.ts
+++ b/site/src/testHelpers/handlers.ts
@@ -385,4 +385,12 @@ export const handlers = [
       )
     },
   ),
+
+  rest.get("/api/v2/deployment/ssh", (_, res, ctx) => {
+    return res(ctx.status(200), ctx.json(M.MockDeploymentSSH))
+  }),
+
+  rest.get("/api/v2/workspaceagents/:agent/startup-logs", (_, res, ctx) => {
+    return res(ctx.status(200), ctx.json(M.MockStartupLogs))
+  }),
 ]