diff --git a/.changeset/large-pillows-clap.md b/.changeset/large-pillows-clap.md
new file mode 100644
index 000000000000..56e9a5952842
--- /dev/null
+++ b/.changeset/large-pillows-clap.md
@@ -0,0 +1,11 @@
+---
+"wrangler": patch
+---
+
+fix: improve authentication logging and warnings
+
+- If a user has previously logged in via Wrangler 1 with an API token, we now display a helpful warning.
+- When logging in and out, we no longer display the path to the internal user auh config file.
+- When logging in, we now display an initial message to indicate the authentication flow is starting.
+
+Fixes [#526](https://github.com/cloudflare/wrangler2/issues/526)
diff --git a/packages/wrangler/src/__tests__/logout.test.ts b/packages/wrangler/src/__tests__/logout.test.ts
index a65f00d6b719..2824934c198f 100644
--- a/packages/wrangler/src/__tests__/logout.test.ts
+++ b/packages/wrangler/src/__tests__/logout.test.ts
@@ -38,10 +38,7 @@ describe("wrangler", () => {
       reinitialiseAuthTokens();
       await runWrangler("logout");
 
-      expect(std.out).toMatchInlineSnapshot(`
-        "💁  Wrangler is configured with an OAuth token. The token has been successfully revoked
-        Removing ./home/.wrangler/config/default.toml.. success!"
-      `);
+      expect(std.out).toMatchInlineSnapshot(`"Successfully logged out."`);
 
       // Make sure that we made the request to logout.
       expect(fetchMock).toHaveBeenCalledTimes(1);
diff --git a/packages/wrangler/src/__tests__/whoami.test.tsx b/packages/wrangler/src/__tests__/whoami.test.tsx
index b54ec5e558e7..d273a8b68b7b 100644
--- a/packages/wrangler/src/__tests__/whoami.test.tsx
+++ b/packages/wrangler/src/__tests__/whoami.test.tsx
@@ -3,11 +3,13 @@ import React from "react";
 import { reinitialiseAuthTokens, writeAuthConfigFile } from "../user";
 import { getUserInfo, WhoAmI } from "../whoami";
 import { setMockResponse } from "./helpers/mock-cfetch";
+import { mockConsoleMethods } from "./helpers/mock-console";
 import { runInTempDir } from "./helpers/run-in-tmp";
 import type { UserInfo } from "../whoami";
 
 describe("getUserInfo()", () => {
   runInTempDir({ homedir: "./home" });
+  const std = mockConsoleMethods();
 
   it("should return undefined if there is no config file", async () => {
     const userInfo = await getUserInfo();
@@ -51,6 +53,17 @@ describe("getUserInfo()", () => {
       ],
     });
   });
+
+  it("should display a warning message if the config file contains a legacy api_token field", async () => {
+    writeAuthConfigFile({ api_token: "API_TOKEN" });
+    await reinitialiseAuthTokens();
+    await getUserInfo();
+    expect(std.warn).toMatchInlineSnapshot(`
+      "It looks like you have used Wrangler 1's \`config\` command to login with an API token.
+      This is no longer supported in the current version of Wrangler.
+      If you wish to authenticate via an API token then please set the \`CLOUDFLARE_API_TOKEN\` environment variable."
+    `);
+  });
 });
 
 describe("WhoAmI component", () => {
diff --git a/packages/wrangler/src/cfetch/internal.ts b/packages/wrangler/src/cfetch/internal.ts
index ff1eabaf2fda..72e725420837 100644
--- a/packages/wrangler/src/cfetch/internal.ts
+++ b/packages/wrangler/src/cfetch/internal.ts
@@ -89,11 +89,11 @@ async function requireLoggedIn(): Promise<void> {
 }
 
 function requireApiToken(): string {
-  const apiToken = getAPIToken();
-  if (!apiToken) {
+  const authToken = getAPIToken();
+  if (!authToken) {
     throw new Error("No API token found.");
   }
-  return apiToken;
+  return authToken;
 }
 
 function addAuthorizationHeader(
diff --git a/packages/wrangler/src/user.tsx b/packages/wrangler/src/user.tsx
index 8ee474ce2dd5..551a1e434f79 100644
--- a/packages/wrangler/src/user.tsx
+++ b/packages/wrangler/src/user.tsx
@@ -270,6 +270,8 @@ interface State extends AuthTokens {
 interface AuthTokens {
   accessToken?: AccessToken;
   refreshToken?: RefreshToken;
+  /** @deprecated - this field was only provided by the deprecated `wrangler1 config` command. */
+  apiToken?: string;
 }
 
 /**
@@ -285,7 +287,8 @@ export interface UserAuthConfig {
   oauth_token?: string;
   refresh_token?: string;
   expiration_time?: string;
-  // api_token?: string;
+  /** @deprecated - this field was only provided by the deprecated `wrangler1 config` command. */
+  api_token?: string;
 }
 
 interface RefreshToken {
@@ -357,7 +360,7 @@ function getAuthTokens(): AuthTokens {
     }
 
     // otherwise try loading from the user auth config file.
-    const { oauth_token, refresh_token, expiration_time } =
+    const { oauth_token, refresh_token, expiration_time, api_token } =
       readAuthConfigFile();
 
     if (oauth_token) {
@@ -369,6 +372,8 @@ function getAuthTokens(): AuthTokens {
         },
         refreshToken: { value: refresh_token ?? "" },
       };
+    } else if (api_token) {
+      return { apiToken: api_token };
     } else {
       return {};
     }
@@ -385,6 +390,13 @@ export function reinitialiseAuthTokens(): void {
 }
 
 export function getAPIToken(): string | undefined {
+  if (LocalState.apiToken) {
+    console.warn(
+      "It looks like you have used Wrangler 1's `config` command to login with an API token.\n" +
+        "This is no longer supported in the current version of Wrangler.\n" +
+        "If you wish to authenticate via an API token then please set the `CLOUDFLARE_API_TOKEN` environment variable."
+    );
+  }
   return LocalState.accessToken?.value;
 }
 
@@ -847,7 +859,7 @@ export async function loginOrRefreshIfRequired(
 ): Promise<boolean> {
   // TODO: if there already is a token, then try refreshing
   // TODO: ask permission before opening browser
-  if (LocalState.accessToken === undefined) {
+  if (!getAPIToken()) {
     // Not logged in.
     // If we are not interactive, we cannot ask the user to login
     return isInteractive && (await login());
@@ -859,6 +871,7 @@ export async function loginOrRefreshIfRequired(
 }
 
 export async function login(props?: LoginProps): Promise<boolean> {
+  console.log("Attempting to login via OAuth...");
   const urlToOpen = await getAuthURL(props?.scopes);
   await openInBrowser(urlToOpen);
   let server: http.Server;
@@ -930,9 +943,7 @@ export async function login(props?: LoginProps): Promise<boolean> {
             res.end(() => {
               finish(true);
             });
-            console.log(
-              `Successfully configured. You can find your configuration file at: ${os.homedir()}/${USER_AUTH_CONFIG_FILE}`
-            );
+            console.log(`Successfully logged in.`);
 
             return;
           }
@@ -1009,12 +1020,8 @@ export async function logout(): Promise<void> {
     },
   });
   await response.text(); // blank text? would be nice if it was something meaningful
-  console.log(
-    "💁  Wrangler is configured with an OAuth token. The token has been successfully revoked"
-  );
-  // delete the file
   rmSync(path.join(os.homedir(), USER_AUTH_CONFIG_FILE));
-  console.log(`Removing ${os.homedir()}/${USER_AUTH_CONFIG_FILE}.. success!`);
+  console.log(`Successfully logged out.`);
 }
 
 export function listScopes(message = "💁 Available scopes:"): void {