diff --git a/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdown.stories.tsx b/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdown.stories.tsx
index 9c488d0ffba28..b6b6baf0c405a 100644
--- a/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdown.stories.tsx
+++ b/site/src/modules/dashboard/Navbar/UserDropdown/UserDropdown.stories.tsx
@@ -31,7 +31,7 @@ const Example: Story = {
 		await step("click to open", async () => {
 			await userEvent.click(canvas.getByRole("button"));
 			await waitFor(() =>
-				expect(screen.getByText(/v99\.999\.9999/i)).toBeInTheDocument(),
+				expect(screen.getByText(/v2\.99\.99/i)).toBeInTheDocument(),
 			);
 		});
 	},
diff --git a/site/src/modules/provisioners/ProvisionerGroup.tsx b/site/src/modules/provisioners/ProvisionerGroup.tsx
index eb8bf154bd808..9b9d3bb539c09 100644
--- a/site/src/modules/provisioners/ProvisionerGroup.tsx
+++ b/site/src/modules/provisioners/ProvisionerGroup.tsx
@@ -1,13 +1,20 @@
-import { useTheme } from "@emotion/react";
+import { type Interpolation, type Theme, useTheme } from "@emotion/react";
 import Business from "@mui/icons-material/Business";
 import Person from "@mui/icons-material/Person";
 import Button from "@mui/material/Button";
+import Link from "@mui/material/Link";
 import Tooltip from "@mui/material/Tooltip";
 import type { BuildInfoResponse, ProvisionerDaemon } from "api/typesGenerated";
 import { DropdownArrow } from "components/DropdownArrow/DropdownArrow";
 import { Pill } from "components/Pill/Pill";
+import {
+	Popover,
+	PopoverContent,
+	PopoverTrigger,
+} from "components/Popover/Popover";
 import { type FC, useState } from "react";
 import { createDayString } from "utils/createDayString";
+import { docs } from "utils/docs";
 import { ProvisionerTag } from "./ProvisionerTag";
 
 type ProvisionerGroupType = "builtin" | "psk" | "key";
@@ -159,14 +166,51 @@ export const ProvisionerGroup: FC<ProvisionerGroupProps> = ({
 								width: 310,
 							}}
 						>
-							<div css={{ lineHeight: "160%" }}>
+							<div css={{ lineHeight: 1.6 }}>
 								<h4 css={{ fontWeight: 500, margin: 0 }}>{provisioner.name}</h4>
-								<span css={{ color: theme.palette.text.secondary }}>
+								<span
+									css={{ color: theme.palette.text.secondary, fontSize: 13 }}
+								>
 									{type === "builtin" ? (
 										<span>Built-in</span>
 									) : (
 										<>
-											{upToDate ? "Up to date" : provisioner.version} &mdash;{" "}
+											<Popover mode="hover">
+												<PopoverTrigger>
+													<span>
+														{buildInfo
+															? provisioner.version === buildInfo.version
+																? "Up to date"
+																: "Out of date"
+															: provisioner.version}
+													</span>
+												</PopoverTrigger>
+												<PopoverContent
+													transformOrigin={{ vertical: -8, horizontal: 0 }}
+													css={{
+														"& .MuiPaper-root": {
+															padding: "20px 20px 8px",
+															maxWidth: 340,
+														},
+													}}
+												>
+													<h4 css={styles.title}>Release version</h4>
+													<p css={styles.text}>{provisioner.version}</p>
+													<h4 css={styles.title}>Protocol version</h4>
+													<p css={styles.text}>{provisioner.api_version}</p>
+													{provisioner.api_version !==
+														buildInfo?.provisioner_api_version && (
+														<p css={[styles.text, { fontSize: 13 }]}>
+															This provisioner is out of date. You may
+															experience issues when using a provisioner version
+															that doesn’t match your Coder deployment. Please
+															upgrade to a newer version.{" "}
+															<Link href={docs("/")}>Learn more…</Link>
+														</p>
+													)}
+												</PopoverContent>
+											</Popover>{" "}
+											&mdash;{" "}
 											{provisioner.last_seen_at && (
 												<span data-chromatic="ignore">
 													Last seen {createDayString(provisioner.last_seen_at)}
@@ -211,3 +255,19 @@ export const ProvisionerGroup: FC<ProvisionerGroupProps> = ({
 		</div>
 	);
 };
+
+const styles = {
+	title: (theme) => ({
+		marginTop: 0,
+		marginBottom: 0,
+		color: theme.palette.text.primary,
+		fontSize: 14,
+		lineHeight: "150%",
+		fontWeight: 600,
+	}),
+
+	text: (theme) => ({
+		marginTop: 0,
+		marginBottom: 12,
+	}),
+} satisfies Record<string, Interpolation<Theme>>;
diff --git a/site/src/pages/ManagementSettingsPage/OrganizationProvisionersPageView.stories.tsx b/site/src/pages/ManagementSettingsPage/OrganizationProvisionersPageView.stories.tsx
index 3960c36358294..1306f0e74b649 100644
--- a/site/src/pages/ManagementSettingsPage/OrganizationProvisionersPageView.stories.tsx
+++ b/site/src/pages/ManagementSettingsPage/OrganizationProvisionersPageView.stories.tsx
@@ -26,6 +26,19 @@ export const Provisioners: Story = {
 			psk: [MockProvisioner, MockUserProvisioner, MockProvisionerWithTags],
 			userAuth: [],
 			keys: new Map([
+				[
+					"ベン",
+					[
+						MockProvisioner,
+						{
+							...MockProvisioner2,
+							version: "2.0.0",
+							api_version: "1.0",
+							warnings: [{ code: "EUNKNOWN", message: "私は時代遅れです" }],
+						},
+					],
+				],
+				["ジャイデン", [MockProvisioner, MockProvisioner2]],
 				[
 					"ケイラ",
 					[
diff --git a/site/src/testHelpers/entities.ts b/site/src/testHelpers/entities.ts
index 989e837a2b3b8..7a6e0b1fd8190 100644
--- a/site/src/testHelpers/entities.ts
+++ b/site/src/testHelpers/entities.ts
@@ -217,7 +217,7 @@ export const MockBuildInfo: TypesGen.BuildInfoResponse = {
 	agent_api_version: "1.0",
 	provisioner_api_version: "1.1",
 	external_url: "file:///mock-url",
-	version: "v99.999.9999+c9cdf14",
+	version: "v2.99.99",
 	dashboard_url: "https:///mock-url",
 	workspace_proxy: false,
 	upgrade_message: "My custom upgrade message",