diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx b/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx
index 2eb39b04d3f43..caa034d77c29f 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/Buttons.tsx
@@ -117,10 +117,8 @@ export const RestartButton: FC<ActionButtonPropsWithWorkspace> = ({
   handleAction,
   loading,
   workspace,
-  disabled,
-  tooltipText,
 }) => {
-  const buttonContent = (
+  return (
     <ButtonGroup
       variant="outlined"
       css={{
@@ -129,13 +127,12 @@ export const RestartButton: FC<ActionButtonPropsWithWorkspace> = ({
           borderLeft: "1px solid #FFF",
         },
       }}
-      disabled={disabled}
     >
       <TopbarButton
         startIcon={<ReplayIcon />}
         onClick={() => handleAction()}
         data-testid="workspace-restart-button"
-        disabled={disabled || loading}
+        disabled={loading}
       >
         {loading ? <>Restarting&hellip;</> : <>Restart&hellip;</>}
       </TopbarButton>
@@ -147,11 +144,20 @@ export const RestartButton: FC<ActionButtonPropsWithWorkspace> = ({
       />
     </ButtonGroup>
   );
+};
 
-  return tooltipText ? (
-    <Tooltip title={tooltipText}>{buttonContent}</Tooltip>
-  ) : (
-    buttonContent
+export const UpdateAndStartButton: FC<ActionButtonProps> = ({
+  handleAction,
+}) => {
+  return (
+    <Tooltip title="This template requires automatic updates on workspace startup. Contact your administrator if you want to preserve the template version.">
+      <TopbarButton
+        startIcon={<PlayCircleOutlineIcon />}
+        onClick={() => handleAction()}
+      >
+        Update and start&hellip;
+      </TopbarButton>
+    </Tooltip>
   );
 };
 
diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx b/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx
index e90d844dbda70..ad79ce1be9c95 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/WorkspaceActions.tsx
@@ -24,6 +24,7 @@ import {
   UpdateButton,
   ActivateButton,
   FavoriteButton,
+  UpdateAndStartButton,
 } from "./Buttons";
 import { type ActionType, abilitiesByWorkspaceStatus } from "./constants";
 import { DebugButton } from "./DebugButton";
@@ -89,6 +90,7 @@ export const WorkspaceActions: FC<WorkspaceActionsProps> = ({
   // A mapping of button type to the corresponding React component
   const buttonMapping: Record<ActionType, ReactNode> = {
     update: <UpdateButton handleAction={handleUpdate} />,
+    updateAndStart: <UpdateAndStartButton handleAction={handleUpdate} />,
     updating: <UpdateButton loading handleAction={handleUpdate} />,
     start: (
       <StartButton
@@ -161,7 +163,13 @@ export const WorkspaceActions: FC<WorkspaceActionsProps> = ({
       data-testid="workspace-actions"
     >
       {canBeUpdated && (
-        <>{isUpdating ? buttonMapping.updating : buttonMapping.update}</>
+        <>
+          {isUpdating
+            ? buttonMapping.updating
+            : workspace.template_require_active_version
+              ? buttonMapping.updateAndStart
+              : buttonMapping.update}
+        </>
       )}
 
       {isRestarting
@@ -236,10 +244,6 @@ function getTooltipText(
     return "This template requires automatic updates on workspace startup, but template administrators can ignore this policy.";
   }
 
-  if (workspace.template_require_active_version) {
-    return "This template requires automatic updates on workspace startup. Contact your administrator if you want to preserve the template version.";
-  }
-
   if (workspace.automatic_updates === "always") {
     return "Automatic updates are enabled for this workspace. Modify the update policy in workspace settings if you want to preserve the template version.";
   }
diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts b/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
index 3c7347cc52864..c2a85da8cb121 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
@@ -1,4 +1,4 @@
-import type { Workspace, WorkspaceStatus } from "api/typesGenerated";
+import type { Workspace } from "api/typesGenerated";
 
 /**
  * An iterable of all action types supported by the workspace UI
@@ -23,6 +23,10 @@ export const actionTypes = [
   "retry",
   "debug",
 
+  // When a template requires updates, we aim to display a distinct update
+  // button that clearly indicates a mandatory update.
+  "updateAndStart",
+
   // These are buttons that should be used with disabled UI elements
   "canceling",
   "deleted",
@@ -52,67 +56,105 @@ export const abilitiesByWorkspaceStatus = (
   const status = workspace.latest_build.status;
   if (status === "failed" && canDebug) {
     return {
-      ...statusToAbility.failed,
       actions: ["retry", "debug"],
+      canCancel: false,
+      canAcceptJobs: true,
     };
   }
 
-  return statusToAbility[status];
-};
+  switch (status) {
+    case "starting": {
+      return {
+        actions: ["starting"],
+        canCancel: true,
+        canAcceptJobs: false,
+      };
+    }
+    case "running": {
+      const actions: ActionType[] = ["stop"];
 
-const statusToAbility: Record<WorkspaceStatus, WorkspaceAbilities> = {
-  starting: {
-    actions: ["starting"],
-    canCancel: true,
-    canAcceptJobs: false,
-  },
-  running: {
-    actions: ["stop", "restart"],
-    canCancel: false,
-    canAcceptJobs: true,
-  },
-  stopping: {
-    actions: ["stopping"],
-    canCancel: true,
-    canAcceptJobs: false,
-  },
-  stopped: {
-    actions: ["start"],
-    canCancel: false,
-    canAcceptJobs: true,
-  },
-  canceled: {
-    actions: ["start", "stop"],
-    canCancel: false,
-    canAcceptJobs: true,
-  },
+      // If the template requires the latest version, we prevent the user from
+      // restarting the workspace without updating it first. In the Buttons
+      // component, we display an UpdateAndStart component to facilitate this.
+      if (!workspace.template_require_active_version) {
+        actions.push("restart");
+      }
 
-  // in the case of an error
-  failed: {
-    actions: ["retry"],
-    canCancel: false,
-    canAcceptJobs: true,
-  },
+      return {
+        actions,
+        canCancel: false,
+        canAcceptJobs: true,
+      };
+    }
+    case "stopping": {
+      return {
+        actions: ["stopping"],
+        canCancel: true,
+        canAcceptJobs: false,
+      };
+    }
+    case "stopped": {
+      const actions: ActionType[] = [];
 
-  // Disabled states
-  canceling: {
-    actions: ["canceling"],
-    canCancel: false,
-    canAcceptJobs: false,
-  },
-  deleting: {
-    actions: ["deleting"],
-    canCancel: true,
-    canAcceptJobs: false,
-  },
-  deleted: {
-    actions: ["deleted"],
-    canCancel: false,
-    canAcceptJobs: false,
-  },
-  pending: {
-    actions: ["pending"],
-    canCancel: false,
-    canAcceptJobs: false,
-  },
+      // If the template requires the latest version, we prevent the user from
+      // starting the workspace without updating it first. In the Buttons
+      // component, we display an UpdateAndStart component to facilitate this.
+      if (!workspace.template_require_active_version) {
+        actions.push("start");
+      }
+
+      return {
+        actions,
+        canCancel: false,
+        canAcceptJobs: true,
+      };
+    }
+    case "canceled": {
+      return {
+        actions: ["start", "stop"],
+        canCancel: false,
+        canAcceptJobs: true,
+      };
+    }
+    case "failed": {
+      return {
+        actions: ["retry"],
+        canCancel: false,
+        canAcceptJobs: true,
+      };
+    }
+
+    // Disabled states
+    case "canceling": {
+      return {
+        actions: ["canceling"],
+        canCancel: false,
+        canAcceptJobs: false,
+      };
+    }
+    case "deleting": {
+      return {
+        actions: ["deleting"],
+        canCancel: true,
+        canAcceptJobs: false,
+      };
+    }
+    case "deleted": {
+      return {
+        actions: ["deleted"],
+        canCancel: false,
+        canAcceptJobs: false,
+      };
+    }
+    case "pending": {
+      return {
+        actions: ["pending"],
+        canCancel: false,
+        canAcceptJobs: false,
+      };
+    }
+    default: {
+      throw new Error(`Unknown workspace status: ${status}`);
+    }
+  }
 };