diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx b/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx
index 12eaf5c9a3edc..f44d22628652d 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx
@@ -11,10 +11,13 @@ import { Workspace, WorkspaceBuildParameter } from "api/typesGenerated";
 import { BuildParametersPopover } from "./BuildParametersPopover";
 import PowerSettingsNewIcon from "@mui/icons-material/PowerSettingsNew";
 import LoadingButton from "@mui/lab/LoadingButton";
+import Tooltip from "@mui/material/Tooltip";
 
 interface WorkspaceAction {
   loading?: boolean;
   handleAction: () => void;
+  disabled?: boolean;
+  tooltipText?: string;
 }
 
 export const UpdateButton: FC<WorkspaceAction> = ({
@@ -55,8 +58,8 @@ export const StartButton: FC<
     workspace: Workspace;
     handleAction: (buildParameters?: WorkspaceBuildParameter[]) => void;
   }
-> = ({ handleAction, workspace, loading }) => {
-  return (
+> = ({ handleAction, workspace, loading, disabled, tooltipText }) => {
+  const buttonContent = (
     <ButtonGroup
       variant="outlined"
       sx={{
@@ -65,12 +68,14 @@ export const StartButton: FC<
           borderLeft: "1px solid #FFF",
         },
       }}
+      disabled={disabled}
     >
       <LoadingButton
         loading={loading}
         loadingPosition="start"
         startIcon={<PlayCircleOutlineIcon />}
         onClick={() => handleAction()}
+        disabled={disabled}
       >
         {loading ? <>Starting&hellip;</> : "Start"}
       </LoadingButton>
@@ -81,6 +86,12 @@ export const StartButton: FC<
       />
     </ButtonGroup>
   );
+
+  return tooltipText ? (
+    <Tooltip title={tooltipText}>{buttonContent}</Tooltip>
+  ) : (
+    buttonContent
+  );
 };
 
 export const StopButton: FC<WorkspaceAction> = ({ handleAction, loading }) => {
@@ -102,8 +113,8 @@ export const RestartButton: FC<
     workspace: Workspace;
     handleAction: (buildParameters?: WorkspaceBuildParameter[]) => void;
   }
-> = ({ handleAction, loading, workspace }) => {
-  return (
+> = ({ handleAction, loading, workspace, disabled, tooltipText }) => {
+  const buttonContent = (
     <ButtonGroup
       variant="outlined"
       sx={{
@@ -112,6 +123,7 @@ export const RestartButton: FC<
           borderLeft: "1px solid #FFF",
         },
       }}
+      disabled={disabled}
     >
       <LoadingButton
         loading={loading}
@@ -119,6 +131,7 @@ export const RestartButton: FC<
         startIcon={<ReplayIcon />}
         onClick={() => handleAction()}
         data-testid="workspace-restart-button"
+        disabled={disabled}
       >
         {loading ? <>Restarting&hellip;</> : <>Restart&hellip;</>}
       </LoadingButton>
@@ -129,6 +142,12 @@ export const RestartButton: FC<
       />
     </ButtonGroup>
   );
+
+  return tooltipText ? (
+    <Tooltip title={tooltipText}>{buttonContent}</Tooltip>
+  ) : (
+    buttonContent
+  );
 };
 
 export const CancelButton: FC<WorkspaceAction> = ({ handleAction }) => {
diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.stories.tsx b/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.stories.tsx
index bbe9afe598fba..e85886da1e1e5 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.stories.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.stories.tsx
@@ -93,3 +93,17 @@ export const RequireActiveVersionStopped: Story = {
     canChangeVersions: false,
   },
 };
+
+export const AlwaysUpdateStarted: Story = {
+  args: {
+    workspace: Mocks.MockOutdatedRunningWorkspaceAlwaysUpdate,
+    canChangeVersions: true,
+  },
+};
+
+export const AlwaysUpdateStopped: Story = {
+  args: {
+    workspace: Mocks.MockOutdatedStoppedWorkspaceAlwaysUpdate,
+    canChangeVersions: true,
+  },
+};
diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx b/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx
index 4efc94df53623..b31962853660f 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx
@@ -30,6 +30,7 @@ import {
   MoreMenuTrigger,
   ThreeDotsButton,
 } from "components/MoreMenu/MoreMenu";
+import { workspaceUpdatePolicy } from "utils/workspace";
 
 export interface WorkspaceActionsProps {
   workspace: Workspace;
@@ -67,15 +68,28 @@ export const WorkspaceActions: FC<WorkspaceActionsProps> = ({
     canCancel,
     canAcceptJobs,
     actions: actionsByStatus,
-  } = actionsByWorkspaceStatus(
-    workspace,
-    workspace.latest_build.status,
-    canChangeVersions,
-  );
+  } = actionsByWorkspaceStatus(workspace, workspace.latest_build.status);
   const canBeUpdated = workspace.outdated && canAcceptJobs;
   const { duplicateWorkspace, isDuplicationReady } =
     useWorkspaceDuplication(workspace);
 
+  const disabled =
+    workspaceUpdatePolicy(workspace, canChangeVersions) === "always" &&
+    workspace.outdated;
+
+  const tooltipText = ((): string => {
+    if (!disabled) {
+      return "";
+    }
+    if (workspace.template_require_active_version) {
+      return "This template requires automatic updates";
+    }
+    if (workspace.automatic_updates === "always") {
+      return "You have enabled automatic updates for this workspace";
+    }
+    return "";
+  })();
+
   // A mapping of button type to the corresponding React component
   const buttonMapping: ButtonMapping = {
     [ButtonTypesEnum.update]: <UpdateButton handleAction={handleUpdate} />,
@@ -83,23 +97,41 @@ export const WorkspaceActions: FC<WorkspaceActionsProps> = ({
       <UpdateButton loading handleAction={handleUpdate} />
     ),
     [ButtonTypesEnum.start]: (
-      <StartButton workspace={workspace} handleAction={handleStart} />
+      <StartButton
+        workspace={workspace}
+        handleAction={handleStart}
+        disabled={disabled}
+        tooltipText={tooltipText}
+      />
     ),
     [ButtonTypesEnum.starting]: (
-      <StartButton loading workspace={workspace} handleAction={handleStart} />
+      <StartButton
+        loading
+        workspace={workspace}
+        handleAction={handleStart}
+        disabled={disabled}
+        tooltipText={tooltipText}
+      />
     ),
     [ButtonTypesEnum.stop]: <StopButton handleAction={handleStop} />,
     [ButtonTypesEnum.stopping]: (
       <StopButton loading handleAction={handleStop} />
     ),
     [ButtonTypesEnum.restart]: (
-      <RestartButton workspace={workspace} handleAction={handleRestart} />
+      <RestartButton
+        workspace={workspace}
+        handleAction={handleRestart}
+        disabled={disabled}
+        tooltipText={tooltipText}
+      />
     ),
     [ButtonTypesEnum.restarting]: (
       <RestartButton
         loading
         workspace={workspace}
         handleAction={handleRestart}
+        disabled={disabled}
+        tooltipText={tooltipText}
       />
     ),
     [ButtonTypesEnum.deleting]: <ActionLoadingButton label="Deleting" />,
diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts b/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
index 4209f15f48f1e..d6f2704a18f80 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
@@ -1,6 +1,5 @@
 import { Workspace, WorkspaceStatus } from "api/typesGenerated";
 import { ReactNode } from "react";
-import { workspaceUpdatePolicy } from "utils/workspace";
 
 // the button types we have
 export enum ButtonTypesEnum {
@@ -34,7 +33,6 @@ interface WorkspaceAbilities {
 export const actionsByWorkspaceStatus = (
   workspace: Workspace,
   status: WorkspaceStatus,
-  canChangeVersions: boolean,
 ): WorkspaceAbilities => {
   if (workspace.dormant_at) {
     return {
@@ -43,25 +41,6 @@ export const actionsByWorkspaceStatus = (
       canAcceptJobs: false,
     };
   }
-  if (
-    workspace.outdated &&
-    workspaceUpdatePolicy(workspace, canChangeVersions) === "always"
-  ) {
-    if (status === "running") {
-      return {
-        actions: [ButtonTypesEnum.stop],
-        canCancel: false,
-        canAcceptJobs: true,
-      };
-    }
-    if (status === "stopped") {
-      return {
-        actions: [],
-        canCancel: false,
-        canAcceptJobs: true,
-      };
-    }
-  }
   return statusToActions[status];
 };
 
diff --git a/site/src/testHelpers/entities.ts b/site/src/testHelpers/entities.ts
index ba8dc0458918a..9693c253235ee 100644
--- a/site/src/testHelpers/entities.ts
+++ b/site/src/testHelpers/entities.ts
@@ -1053,6 +1053,17 @@ export const MockOutdatedRunningWorkspaceRequireActiveVersion: TypesGen.Workspac
     },
   };
 
+export const MockOutdatedRunningWorkspaceAlwaysUpdate: TypesGen.Workspace = {
+  ...MockWorkspace,
+  id: "test-outdated-workspace-always-update",
+  outdated: true,
+  automatic_updates: "always",
+  latest_build: {
+    ...MockWorkspaceBuild,
+    status: "running",
+  },
+};
+
 export const MockOutdatedStoppedWorkspaceRequireActiveVersion: TypesGen.Workspace =
   {
     ...MockOutdatedRunningWorkspaceRequireActiveVersion,
@@ -1062,6 +1073,14 @@ export const MockOutdatedStoppedWorkspaceRequireActiveVersion: TypesGen.Workspac
     },
   };
 
+export const MockOutdatedStoppedWorkspaceAlwaysUpdate: TypesGen.Workspace = {
+  ...MockOutdatedRunningWorkspaceAlwaysUpdate,
+  latest_build: {
+    ...MockWorkspaceBuild,
+    status: "stopped",
+  },
+};
+
 export const MockPendingWorkspace: TypesGen.Workspace = {
   ...MockWorkspace,
   id: "test-pending-workspace",