diff --git a/site/src/components/Resources/AgentRow.stories.tsx b/site/src/components/Resources/AgentRow.stories.tsx
index 7a74352db92fc..4871030bfbd19 100644
--- a/site/src/components/Resources/AgentRow.stories.tsx
+++ b/site/src/components/Resources/AgentRow.stories.tsx
@@ -3,6 +3,9 @@ import {
   MockWorkspace,
   MockWorkspaceAgent,
   MockWorkspaceAgentConnecting,
+  MockWorkspaceAgentStartError,
+  MockWorkspaceAgentStarting,
+  MockWorkspaceAgentStartTimeout,
   MockWorkspaceAgentTimeout,
   MockWorkspaceApp,
 } from "testHelpers/entities"
@@ -86,6 +89,30 @@ Timeout.args = {
   showApps: true,
 }
 
+export const Starting = Template.bind({})
+Starting.args = {
+  agent: MockWorkspaceAgentStarting,
+  workspace: MockWorkspace,
+  applicationsHost: "",
+  showApps: true,
+}
+
+export const StartTimeout = Template.bind({})
+StartTimeout.args = {
+  agent: MockWorkspaceAgentStartTimeout,
+  workspace: MockWorkspace,
+  applicationsHost: "",
+  showApps: true,
+}
+
+export const StartError = Template.bind({})
+StartError.args = {
+  agent: MockWorkspaceAgentStartError,
+  workspace: MockWorkspace,
+  applicationsHost: "",
+  showApps: true,
+}
+
 export const ShowingPortForward = Template.bind({})
 ShowingPortForward.args = {
   agent: MockWorkspaceAgent,
diff --git a/site/src/components/Resources/AgentStatus.tsx b/site/src/components/Resources/AgentStatus.tsx
index 48de1597c8ca3..b607d3201b5a2 100644
--- a/site/src/components/Resources/AgentStatus.tsx
+++ b/site/src/components/Resources/AgentStatus.tsx
@@ -13,19 +13,146 @@ import {
 import { useRef, useState } from "react"
 import Link from "@material-ui/core/Link"
 
-const ConnectedStatus: React.FC = () => {
+// If we think in the agent status and lifecycle into a single enum/state I’d
+// say we would have: connecting, timeout, disconnected, connected:created,
+// connected:starting, connected:start_timeout, connected:start_error,
+// connected:ready
+
+const ReadyLifeCycle: React.FC = () => {
   const styles = useStyles()
   const { t } = useTranslation("workspacePage")
 
   return (
     <div
       role="status"
-      aria-label={t("agentStatus.connected")}
+      aria-label={t("agentStatus.connected.ready")}
       className={combineClasses([styles.status, styles.connected])}
     />
   )
 }
 
+const StartingLifecycle: React.FC = () => {
+  const styles = useStyles()
+  const { t } = useTranslation("workspacePage")
+
+  return (
+    <Tooltip title={t("agentStatus.connected.starting")}>
+      <div
+        role="status"
+        aria-label={t("agentStatus.connected.starting")}
+        className={combineClasses([styles.status, styles.connecting])}
+      />
+    </Tooltip>
+  )
+}
+
+const StartTimeoutLifecycle: React.FC<{
+  agent: WorkspaceAgent
+}> = ({ agent }) => {
+  const { t } = useTranslation("agent")
+  const styles = useStyles()
+  const anchorRef = useRef<SVGSVGElement>(null)
+  const [isOpen, setIsOpen] = useState(false)
+  const id = isOpen ? "timeout-popover" : undefined
+
+  return (
+    <>
+      <WarningRounded
+        ref={anchorRef}
+        onMouseEnter={() => setIsOpen(true)}
+        onMouseLeave={() => setIsOpen(false)}
+        role="status"
+        aria-label={t("status.startTimeout")}
+        className={styles.timeoutWarning}
+      />
+      <HelpPopover
+        id={id}
+        open={isOpen}
+        anchorEl={anchorRef.current}
+        onOpen={() => setIsOpen(true)}
+        onClose={() => setIsOpen(false)}
+      >
+        <HelpTooltipTitle>{t("startTimeoutTooltip.title")}</HelpTooltipTitle>
+        <HelpTooltipText>
+          {t("startTimeoutTooltip.message")}{" "}
+          <Link
+            target="_blank"
+            rel="noreferrer"
+            href={agent.troubleshooting_url}
+          >
+            {t("startTimeoutTooltip.link")}
+          </Link>
+          .
+        </HelpTooltipText>
+      </HelpPopover>
+    </>
+  )
+}
+
+const StartErrorLifecycle: React.FC<{
+  agent: WorkspaceAgent
+}> = ({ agent }) => {
+  const { t } = useTranslation("agent")
+  const styles = useStyles()
+  const anchorRef = useRef<SVGSVGElement>(null)
+  const [isOpen, setIsOpen] = useState(false)
+  const id = isOpen ? "timeout-popover" : undefined
+
+  return (
+    <>
+      <WarningRounded
+        ref={anchorRef}
+        onMouseEnter={() => setIsOpen(true)}
+        onMouseLeave={() => setIsOpen(false)}
+        role="status"
+        aria-label={t("status.error")}
+        className={styles.errorWarning}
+      />
+      <HelpPopover
+        id={id}
+        open={isOpen}
+        anchorEl={anchorRef.current}
+        onOpen={() => setIsOpen(true)}
+        onClose={() => setIsOpen(false)}
+      >
+        <HelpTooltipTitle>{t("startErrorTooltip.title")}</HelpTooltipTitle>
+        <HelpTooltipText>
+          {t("startErrorTooltip.message")}{" "}
+          <Link
+            target="_blank"
+            rel="noreferrer"
+            href={agent.troubleshooting_url}
+          >
+            {t("startErrorTooltip.link")}
+          </Link>
+          .
+        </HelpTooltipText>
+      </HelpPopover>
+    </>
+  )
+}
+
+const ConnectedStatus: React.FC<{
+  agent: WorkspaceAgent
+}> = ({ agent }) => {
+  return (
+    <ChooseOne>
+      <Cond condition={agent.lifecycle_state === "ready"}>
+        <ReadyLifeCycle />
+      </Cond>
+      <Cond condition={agent.lifecycle_state === "start_timeout"}>
+        <StartTimeoutLifecycle agent={agent} />
+      </Cond>
+      <Cond condition={agent.lifecycle_state === "start_error"}>
+        <StartErrorLifecycle agent={agent} />
+      </Cond>
+      <Cond>
+        <StartingLifecycle />
+      </Cond>
+    </ChooseOne>
+  )
+}
+
 const DisconnectedStatus: React.FC = () => {
   const styles = useStyles()
   const { t } = useTranslation("workspacePage")
@@ -105,7 +232,7 @@ export const AgentStatus: React.FC<{
   return (
     <ChooseOne>
       <Cond condition={agent.status === "connected"}>
-        <ConnectedStatus />
+        <ConnectedStatus agent={agent} />
       </Cond>
       <Cond condition={agent.status === "disconnected"}>
         <DisconnectedStatus />
@@ -160,4 +287,12 @@ const useStyles = makeStyles((theme) => ({
     position: "relative",
     top: theme.spacing(1),
   },
+
+  errorWarning: {
+    color: theme.palette.error.main,
+    width: theme.spacing(2.5),
+    height: theme.spacing(2.5),
+    position: "relative",
+    top: theme.spacing(1),
+  },
 }))
diff --git a/site/src/i18n/en/agent.json b/site/src/i18n/en/agent.json
index e2edf8805432d..e30049da483dd 100644
--- a/site/src/i18n/en/agent.json
+++ b/site/src/i18n/en/agent.json
@@ -12,12 +12,24 @@
     "noApps": "None"
   },
   "status": {
-    "timeout": "Timeout"
+    "timeout": "Timeout",
+    "startTimeout": "Start Timeout",
+    "startError": "Error"
   },
   "timeoutTooltip": {
     "title": "Agent is taking too long to connect",
     "message": "We noticed this agent is taking longer than expected to connect.",
     "link": "Troubleshoot"
   },
+  "startTimeoutTooltip": {
+    "title": "Agent is taking too long to start",
+    "message": "We noticed this agent is taking longer than expected to start.",
+    "link": "Troubleshoot"
+  },
+  "startErrorTooltip": {
+    "title": "Error starting agent",
+    "message": "Something went wrong during the agent start.",
+    "link": "Troubleshoot"
+  },
   "unableToConnect": "Unable to connect"
 }
diff --git a/site/src/i18n/en/workspacePage.json b/site/src/i18n/en/workspacePage.json
index 2a8820daf5188..17f7e2aba3941 100644
--- a/site/src/i18n/en/workspacePage.json
+++ b/site/src/i18n/en/workspacePage.json
@@ -36,7 +36,10 @@
     "pending": "Pending"
   },
   "agentStatus": {
-    "connected": "Connected",
+    "connected": {
+      "ready": "Ready",
+      "starting": "Starting..."
+    },
     "connecting": "Connecting...",
     "disconnected": "Disconnected",
     "timeout": "Timeout"
diff --git a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
index c6fedc3ffeb13..2110e27ada732 100644
--- a/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
+++ b/site/src/pages/WorkspacePage/WorkspacePage.test.tsx
@@ -18,11 +18,7 @@ import {
   MockStoppingWorkspace,
   MockTemplate,
   MockWorkspace,
-  MockWorkspaceAgent,
-  MockWorkspaceAgentConnecting,
-  MockWorkspaceAgentDisconnected,
   MockWorkspaceBuild,
-  MockWorkspaceResource2,
   renderWithAuth,
   waitForLoaderToBeRemoved,
 } from "../../testHelpers/renderHelpers"
@@ -284,65 +280,4 @@ describe("WorkspacePage", () => {
       })
     })
   })
-
-  describe("Resources", () => {
-    it("shows the status of each agent in each resource", async () => {
-      const getTemplateMock = jest
-        .spyOn(api, "getTemplate")
-        .mockResolvedValueOnce(MockTemplate)
-
-      const workspaceWithResources = {
-        ...MockWorkspace,
-        latest_build: {
-          ...MockWorkspaceBuild,
-          resources: [
-            {
-              ...MockWorkspaceResource2,
-              agents: [
-                MockWorkspaceAgent,
-                MockWorkspaceAgentDisconnected,
-                MockWorkspaceAgentConnecting,
-              ],
-            },
-          ],
-        },
-      }
-
-      server.use(
-        rest.get(
-          `/api/v2/users/:username/workspace/:workspaceName`,
-          (req, res, ctx) => {
-            return res(ctx.status(200), ctx.json(workspaceWithResources))
-          },
-        ),
-      )
-
-      await renderWorkspacePage()
-      const agent1Names = await screen.findAllByText(MockWorkspaceAgent.name)
-      expect(agent1Names.length).toEqual(1)
-      const agent2Names = await screen.findAllByText(
-        MockWorkspaceAgentDisconnected.name,
-      )
-      expect(agent2Names.length).toEqual(2)
-      const agent1Status = await screen.findAllByLabelText(
-        t<string>(`agentStatus.${MockWorkspaceAgent.status}`, {
-          ns: "workspacePage",
-        }),
-      )
-      expect(agent1Status.length).toEqual(1)
-      const agentDisconnected = await screen.findAllByLabelText(
-        t<string>(`agentStatus.${MockWorkspaceAgentDisconnected.status}`, {
-          ns: "workspacePage",
-        }),
-      )
-      expect(agentDisconnected.length).toEqual(1)
-      const agentConnecting = await screen.findAllByLabelText(
-        t<string>(`agentStatus.${MockWorkspaceAgentConnecting.status}`, {
-          ns: "workspacePage",
-        }),
-      )
-      expect(agentConnecting.length).toEqual(1)
-      expect(getTemplateMock).toBeCalled()
-    })
-  })
 })