diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6b496590..315a7d47 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,12 @@
 
 ## Unreleased
 
+### Added
+
+- Default URL setting that takes precedence over CODER_URL.
+- Autologin setting that automatically initiates login when the extension
+  activates using either the default URL or CODER_URL.
+
 ## [v1.3.5](https://github.com/coder/vscode-coder/releases/tag/v1.3.5) (2024-10-16)
 
 ### Fixed
diff --git a/package.json b/package.json
index 51994d82..2a78c176 100644
--- a/package.json
+++ b/package.json
@@ -97,6 +97,16 @@
           "markdownDescription": "If not set, will inherit from the `no_proxy` or `NO_PROXY` environment variables. `http.proxySupport` must be set to `on` or `off`, otherwise VS Code will override the proxy agent set by the plugin.",
           "type": "string",
           "default": ""
+        },
+        "coder.defaultUrl": {
+          "markdownDescription": "This will be shown in the URL prompt, along with CODER_URL if set, for the user to select when logging in. If autologin is enabled, this URL will be automatically logged into when the extension is activated.",
+          "type": "string",
+          "default": ""
+        },
+        "coder.autologin": {
+          "markdownDescription": "Automatically log into the default URL or CODER_URL when the extension is activated. Has no effect if neither is set.",
+          "type": "boolean",
+          "default": false
         }
       }
     },
diff --git a/src/commands.ts b/src/commands.ts
index cf5850ad..516c90b3 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -78,13 +78,14 @@ export class Commands {
    * CODER_URL or enter a new one.  Undefined means the user aborted.
    */
   private async askURL(selection?: string): Promise<string | undefined> {
+    const defaultURL = vscode.workspace.getConfiguration().get<string>("coder.defaultUrl") ?? ""
     const quickPick = vscode.window.createQuickPick()
-    quickPick.value = selection || process.env.CODER_URL || ""
+    quickPick.value = selection || defaultURL || process.env.CODER_URL || ""
     quickPick.placeholder = "https://example.coder.com"
     quickPick.title = "Enter the URL of your Coder deployment."
 
     // Initial items.
-    quickPick.items = this.storage.withUrlHistory(process.env.CODER_URL).map((url) => ({
+    quickPick.items = this.storage.withUrlHistory(defaultURL, process.env.CODER_URL).map((url) => ({
       alwaysShow: true,
       label: url,
     }))
@@ -93,7 +94,7 @@ export class Commands {
     // an option in case the user wants to connect to something that is not in
     // the list.
     quickPick.onDidChangeValue((value) => {
-      quickPick.items = this.storage.withUrlHistory(process.env.CODER_URL, value).map((url) => ({
+      quickPick.items = this.storage.withUrlHistory(defaultURL, process.env.CODER_URL, value).map((url) => ({
         alwaysShow: true,
         label: url,
       }))
@@ -111,8 +112,8 @@ export class Commands {
 
   /**
    * Ask the user for the URL if it was not provided, letting them choose from a
-   * list of recent URLs or CODER_URL or enter a new one, and normalizes the
-   * returned URL.  Undefined means the user aborted.
+   * list of recent URLs or the default URL or CODER_URL or enter a new one, and
+   * normalizes the returned URL.  Undefined means the user aborted.
    */
   public async maybeAskUrl(providedUrl: string | undefined | null, lastUsedUrl?: string): Promise<string | undefined> {
     let url = providedUrl || (await this.askURL(lastUsedUrl))
@@ -134,7 +135,8 @@ export class Commands {
 
   /**
    * Log into the provided deployment.  If the deployment URL is not specified,
-   * ask for it first with a menu showing recent URLs and CODER_URL, if set.
+   * ask for it first with a menu showing recent URLs along with the default URL
+   * and CODER_URL, if those are set.
    */
   public async login(...args: string[]): Promise<void> {
     // Destructure would be nice but VS Code can pass undefined which errors.
diff --git a/src/extension.ts b/src/extension.ts
index 2235683c..92f7296b 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -215,5 +215,14 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
   } else {
     storage.writeToCoderOutputChannel("Not currently logged in")
     vscode.commands.executeCommand("setContext", "coder.loaded", true)
+
+    // Handle autologin, if not already logged in.
+    const cfg = vscode.workspace.getConfiguration()
+    if (cfg.get("coder.autologin") === true) {
+      const defaultUrl = cfg.get("coder.defaultUrl") || process.env.CODER_URL
+      if (defaultUrl) {
+        vscode.commands.executeCommand("coder.login", defaultUrl)
+      }
+    }
   }
 }