diff --git a/src/commands.ts b/src/commands.ts
index c099a34f..3c0792ef 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -8,6 +8,34 @@ import { Remote } from "./remote"
 import { Storage } from "./storage"
 import { OpenableTreeItem } from "./workspacesProvider"
 
+// maybeAskUrl asks the user for the URL if it was not provided and normalizes
+// the returned URL.
+export async function maybeAskUrl(
+  providedUrl: string | undefined | null,
+  lastUsedUrl?: string,
+): Promise<string | undefined> {
+  let url =
+    providedUrl ||
+    (await vscode.window.showInputBox({
+      title: "Coder URL",
+      prompt: "Enter the URL of your Coder deployment.",
+      placeHolder: "https://example.coder.com",
+      value: lastUsedUrl,
+    }))
+  if (!url) {
+    return undefined
+  }
+  if (!url.startsWith("http://") && !url.startsWith("https://")) {
+    // Default to HTTPS if not provided!
+    // https://github.com/coder/vscode-coder/issues/44
+    url = "https://" + url
+  }
+  while (url.endsWith("/")) {
+    url = url.substring(0, url.length - 1)
+  }
+  return url
+}
+
 export class Commands {
   public constructor(
     private readonly vscodeProposed: typeof vscode,
@@ -15,26 +43,7 @@ export class Commands {
   ) {}
 
   public async login(...args: string[]): Promise<void> {
-    let url: string | undefined = args.length >= 1 ? args[0] : undefined
-    if (!url) {
-      url = await vscode.window.showInputBox({
-        title: "Coder URL",
-        prompt: "Enter the URL of your Coder deployment.",
-        placeHolder: "https://example.coder.com",
-        value: url,
-      })
-    }
-    if (!url) {
-      return
-    }
-    if (!url.startsWith("http://") && !url.startsWith("https://")) {
-      // Default to HTTPS if not provided!
-      // https://github.com/coder/vscode-coder/issues/44
-      url = "https://" + url
-    }
-    while (url.endsWith("/")) {
-      url = url.substring(0, url.length - 1)
-    }
+    const url = await maybeAskUrl(args[0])
     let token: string | undefined = args.length >= 2 ? args[1] : undefined
     if (!token) {
       const opened = await vscode.env.openExternal(vscode.Uri.parse(`${url}/cli-auth`))
diff --git a/src/extension.ts b/src/extension.ts
index 1bb82b84..7aa73f94 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -127,14 +127,25 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
           throw new Error("workspace must be specified as a query parameter")
         }
 
-        const url = params.get("url")
-        const token = params.get("token")
+        // We are not guaranteed that the URL we currently have is for the URL
+        // this workspace belongs to, or that we even have a URL at all (the
+        // queries will default to localhost) so ask for it if missing.
+        // Pre-populate in case we do have the right URL so the user can just
+        // hit enter and move on.
+        const url = await maybeAskUrl(params.get("url"), storage.getURL())
         if (url) {
           await storage.setURL(url)
+        } else {
+          throw new Error("url must be provided or specified as a query parameter")
         }
+
+        // If the token is missing we will get a 401 later and the user will be
+        // prompted to sign in again, so we do not need to ensure it is set.
+        const token = params.get("token")
         if (token) {
           await storage.setSessionToken(token)
         }
+
         vscode.commands.executeCommand("coder.open", owner, workspace, agent, folder)
       }
     },