diff --git a/src/error.ts b/src/error.ts
index 0e9babd9..31723fd3 100644
--- a/src/error.ts
+++ b/src/error.ts
@@ -1,4 +1,5 @@
 import { isAxiosError } from "axios"
+import { isApiError, isApiErrorResponse } from "coder/site/src/api/errors"
 import * as forge from "node-forge"
 import * as tls from "tls"
 import * as vscode from "vscode"
@@ -157,3 +158,14 @@ export class CertificateError extends Error {
     }
   }
 }
+
+// getErrorDetail is copied from coder/site, but changes the default return.
+export const getErrorDetail = (error: unknown): string | undefined | null => {
+  if (isApiError(error)) {
+    return error.response.data.detail
+  }
+  if (isApiErrorResponse(error)) {
+    return error.detail
+  }
+  return null
+}
diff --git a/src/extension.ts b/src/extension.ts
index dfcfb324..c499d576 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -1,13 +1,14 @@
 "use strict"
-import axios from "axios"
+import axios, { isAxiosError } from "axios"
 import { getAuthenticatedUser } from "coder/site/src/api/api"
+import { getErrorMessage } from "coder/site/src/api/errors"
 import fs from "fs"
 import * as https from "https"
 import * as module from "module"
 import * as os from "os"
 import * as vscode from "vscode"
 import { Commands } from "./commands"
-import { CertificateError } from "./error"
+import { CertificateError, getErrorDetail } from "./error"
 import { Remote } from "./remote"
 import { Storage } from "./storage"
 import { WorkspaceQuery, WorkspaceProvider } from "./workspacesProvider"
@@ -199,13 +200,38 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
   try {
     await remote.setup(vscodeProposed.env.remoteAuthority)
   } catch (ex) {
-    if (ex instanceof CertificateError) {
-      return await ex.showModal("Failed to open workspace")
+    switch (true) {
+      case ex instanceof CertificateError:
+        await ex.showModal("Failed to open workspace")
+        break
+      case isAxiosError(ex):
+        {
+          const msg = getErrorMessage(ex, "")
+          const detail = getErrorDetail(ex)
+          const urlString = axios.getUri(ex.response?.config)
+          let path = urlString
+          try {
+            path = new URL(urlString).pathname
+          } catch (e) {
+            // ignore, default to full url
+          }
+
+          await vscodeProposed.window.showErrorMessage("Failed to open workspace", {
+            detail: `API ${ex.response?.config.method?.toUpperCase()} to '${path}' failed with code ${ex.response?.status}.\nMessage: ${msg}\nDetail: ${detail}`,
+            modal: true,
+            useCustom: true,
+          })
+        }
+        break
+      default:
+        await vscodeProposed.window.showErrorMessage("Failed to open workspace", {
+          detail: (ex as string).toString(),
+          modal: true,
+          useCustom: true,
+        })
     }
-    await vscodeProposed.window.showErrorMessage("Failed to open workspace", {
-      detail: (ex as string).toString(),
-      modal: true,
-      useCustom: true,
-    })
+
+    // Always close remote session when we fail to open a workspace.
+    await remote.closeRemote()
   }
 }
diff --git a/src/remote.ts b/src/remote.ts
index 4f504e79..9b19bee2 100644
--- a/src/remote.ts
+++ b/src/remote.ts
@@ -137,23 +137,33 @@ export class Remote {
 
     let buildComplete: undefined | (() => void)
     if (this.storage.workspace.latest_build.status === "stopped") {
+      // If the workspace requires the latest active template version, we should attempt
+      // to update that here.
+      // TODO: If param set changes, what do we do??
+      const versionID = this.storage.workspace.template_require_active_version
+        ? // Use the latest template version
+          this.storage.workspace.template_active_version_id
+        : // Default to not updating the workspace if not required.
+          this.storage.workspace.latest_build.template_version_id
+
       this.vscodeProposed.window.withProgress(
         {
           location: vscode.ProgressLocation.Notification,
           cancellable: false,
-          title: "Starting workspace...",
+          title: this.storage.workspace.template_require_active_version
+            ? "Updating workspace..."
+            : "Starting workspace...",
         },
         () =>
           new Promise<void>((r) => {
             buildComplete = r
           }),
       )
+
+      const latestBuild = await startWorkspace(this.storage.workspace.id, versionID)
       this.storage.workspace = {
         ...this.storage.workspace,
-        latest_build: await startWorkspace(
-          this.storage.workspace.id,
-          this.storage.workspace.latest_build.template_version_id,
-        ),
+        latest_build: latestBuild,
       }
     }
 
@@ -796,7 +806,7 @@ export class Remote {
   }
 
   // closeRemote ends the current remote session.
-  private async closeRemote() {
+  public async closeRemote() {
     await vscode.commands.executeCommand("workbench.action.remote.close")
   }