diff --git a/__tests__/cmds/categories/create.test.ts b/__tests__/cmds/categories/create.test.ts
index 965d783ff..99a35450a 100644
--- a/__tests__/cmds/categories/create.test.ts
+++ b/__tests__/cmds/categories/create.test.ts
@@ -1,4 +1,5 @@
 import nock from 'nock';
+import prompts from 'prompts';
 
 import CategoriesCreateCommand from '../../../src/cmds/categories/create';
 import getAPIMock, { getAPIMockWithVersionHeader } from '../../helpers/get-api-mock';
@@ -13,10 +14,19 @@ describe('rdme categories:create', () => {
 
   afterEach(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(categoriesCreate.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(categoriesCreate.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(categoriesCreate.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should error if no title provided', () => {
diff --git a/__tests__/cmds/categories/index.test.ts b/__tests__/cmds/categories/index.test.ts
index d19a195a8..0c9bf8956 100644
--- a/__tests__/cmds/categories/index.test.ts
+++ b/__tests__/cmds/categories/index.test.ts
@@ -1,4 +1,5 @@
 import nock from 'nock';
+import prompts from 'prompts';
 
 import CategoriesCommand from '../../../src/cmds/categories';
 import getAPIMock, { getAPIMockWithVersionHeader } from '../../helpers/get-api-mock';
@@ -13,10 +14,19 @@ describe('rdme categories', () => {
 
   afterEach(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(categories.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(categories.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(categories.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should return all categories for a single page', async () => {
diff --git a/__tests__/cmds/changelogs/index.test.ts b/__tests__/cmds/changelogs/index.test.ts
index a167c621e..1640db25c 100644
--- a/__tests__/cmds/changelogs/index.test.ts
+++ b/__tests__/cmds/changelogs/index.test.ts
@@ -4,6 +4,7 @@ import path from 'path';
 import chalk from 'chalk';
 import frontMatter from 'gray-matter';
 import nock from 'nock';
+import prompts from 'prompts';
 
 import ChangelogsCommand from '../../../src/cmds/changelogs';
 import APIError from '../../../src/lib/apiError';
@@ -21,10 +22,19 @@ describe('rdme changelogs', () => {
 
   afterAll(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(changelogs.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(changelogs.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(changelogs.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should error if no folder provided', () => {
diff --git a/__tests__/cmds/changelogs/single.test.ts b/__tests__/cmds/changelogs/single.test.ts
index b808bdade..d20541e80 100644
--- a/__tests__/cmds/changelogs/single.test.ts
+++ b/__tests__/cmds/changelogs/single.test.ts
@@ -4,6 +4,7 @@ import path from 'path';
 import chalk from 'chalk';
 import frontMatter from 'gray-matter';
 import nock from 'nock';
+import prompts from 'prompts';
 
 import SingleChangelogCommand from '../../../src/cmds/changelogs/single';
 import APIError from '../../../src/lib/apiError';
@@ -21,10 +22,19 @@ describe('rdme changelogs:single', () => {
 
   afterAll(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(changelogsSingle.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(changelogsSingle.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(changelogsSingle.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should error if no file path provided', () => {
diff --git a/__tests__/cmds/custompages/index.test.ts b/__tests__/cmds/custompages/index.test.ts
index 375bd7b26..c1541e7c8 100644
--- a/__tests__/cmds/custompages/index.test.ts
+++ b/__tests__/cmds/custompages/index.test.ts
@@ -4,6 +4,7 @@ import path from 'path';
 import chalk from 'chalk';
 import frontMatter from 'gray-matter';
 import nock from 'nock';
+import prompts from 'prompts';
 
 import CustomPagesCommand from '../../../src/cmds/custompages';
 import APIError from '../../../src/lib/apiError';
@@ -21,10 +22,19 @@ describe('rdme custompages', () => {
 
   afterAll(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(custompages.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(custompages.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(custompages.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should error if no folder provided', () => {
diff --git a/__tests__/cmds/custompages/single.test.ts b/__tests__/cmds/custompages/single.test.ts
index b7c880c47..27dbb55df 100644
--- a/__tests__/cmds/custompages/single.test.ts
+++ b/__tests__/cmds/custompages/single.test.ts
@@ -4,6 +4,7 @@ import path from 'path';
 import chalk from 'chalk';
 import frontMatter from 'gray-matter';
 import nock from 'nock';
+import prompts from 'prompts';
 
 import SingleCustomPageCommand from '../../../src/cmds/custompages/single';
 import APIError from '../../../src/lib/apiError';
@@ -21,10 +22,19 @@ describe('rdme custompages:single', () => {
 
   afterAll(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(customPagesSingle.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(customPagesSingle.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(customPagesSingle.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should error if no file path provided', () => {
diff --git a/__tests__/cmds/docs/edit.test.ts b/__tests__/cmds/docs/edit.test.ts
index bd23401cb..a67a04670 100644
--- a/__tests__/cmds/docs/edit.test.ts
+++ b/__tests__/cmds/docs/edit.test.ts
@@ -1,5 +1,8 @@
 import fs from 'fs';
 
+import nock from 'nock';
+import prompts from 'prompts';
+
 import DocsEditCommand from '../../../src/cmds/docs/edit';
 import APIError from '../../../src/lib/apiError';
 import getAPIMock, { getAPIMockWithVersionHeader } from '../../helpers/get-api-mock';
@@ -11,10 +14,21 @@ const version = '1.0.0';
 const category = 'CATEGORY_ID';
 
 describe('rdme docs:edit', () => {
-  it('should error if no api key provided', () => {
-    return expect(docsEdit.run({})).rejects.toStrictEqual(
-      new Error('No project API key provided. Please use `--key`.')
-    );
+  beforeAll(() => nock.disableNetConnect());
+
+  afterAll(() => nock.cleanAll());
+
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(docsEdit.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(docsEdit.run({})).rejects.toStrictEqual(new Error('No project API key provided. Please use `--key`.'));
+    delete process.env.TEST_CI;
   });
 
   it('should error if no slug provided', () => {
diff --git a/__tests__/cmds/docs/index.test.ts b/__tests__/cmds/docs/index.test.ts
index 19039aac1..d92d26aff 100644
--- a/__tests__/cmds/docs/index.test.ts
+++ b/__tests__/cmds/docs/index.test.ts
@@ -31,8 +31,17 @@ describe('rdme docs', () => {
 
   afterAll(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(docs.run({})).rejects.toStrictEqual(new Error('No project API key provided. Please use `--key`.'));
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(docs.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(docs.run({})).rejects.toStrictEqual(new Error('No project API key provided. Please use `--key`.'));
+    delete process.env.TEST_CI;
   });
 
   it('should error if no folder provided', () => {
diff --git a/__tests__/cmds/docs/single.test.ts b/__tests__/cmds/docs/single.test.ts
index 8b3ae719c..4e6878662 100644
--- a/__tests__/cmds/docs/single.test.ts
+++ b/__tests__/cmds/docs/single.test.ts
@@ -4,6 +4,7 @@ import path from 'path';
 import chalk from 'chalk';
 import frontMatter from 'gray-matter';
 import nock from 'nock';
+import prompts from 'prompts';
 
 import DocsSingleCommand from '../../../src/cmds/docs/single';
 import APIError from '../../../src/lib/apiError';
@@ -24,10 +25,19 @@ describe('rdme docs:single', () => {
 
   afterAll(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(docsSingle.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(docsSingle.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(docsSingle.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should error if no file path provided', () => {
diff --git a/__tests__/cmds/login.test.ts b/__tests__/cmds/login.test.ts
index 7774b9baa..36833fc03 100644
--- a/__tests__/cmds/login.test.ts
+++ b/__tests__/cmds/login.test.ts
@@ -36,7 +36,7 @@ describe('rdme login', () => {
   it('should post to /login on the API', async () => {
     prompts.inject([email, password, project]);
 
-    const mock = getAPIMock().post('/api/v1/login').reply(200, { apiKey });
+    const mock = getAPIMock().post('/api/v1/login', { email, password, project }).reply(200, { apiKey });
 
     await expect(cmd.run({})).resolves.toBe('Successfully logged in as user@example.com to the subdomain project.');
 
@@ -50,7 +50,7 @@ describe('rdme login', () => {
   it('should post to /login on the API if passing in project via opt', async () => {
     prompts.inject([email, password]);
 
-    const mock = getAPIMock().post('/api/v1/login').reply(200, { apiKey });
+    const mock = getAPIMock().post('/api/v1/login', { email, password, project }).reply(200, { apiKey });
 
     await expect(cmd.run({ project })).resolves.toBe(
       'Successfully logged in as user@example.com to the subdomain project.'
diff --git a/__tests__/cmds/openapi/index.test.ts b/__tests__/cmds/openapi/index.test.ts
index 91b8a29bd..22915e9e8 100644
--- a/__tests__/cmds/openapi/index.test.ts
+++ b/__tests__/cmds/openapi/index.test.ts
@@ -839,10 +839,17 @@ describe('rdme openapi', () => {
   });
 
   describe('error handling', () => {
-    it('should error if no api key provided', () => {
-      return expect(
-        openapi.run({ spec: require.resolve('@readme/oas-examples/3.0/json/petstore.json') })
-      ).rejects.toStrictEqual(new Error('No project API key provided. Please use `--key`.'));
+    it('should prompt for login if no API key provided', () => {
+      prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+      return expect(openapi.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    });
+
+    it('should error in CI if no API key provided', async () => {
+      process.env.TEST_CI = 'true';
+      await expect(openapi.run({})).rejects.toStrictEqual(
+        new Error('No project API key provided. Please use `--key`.')
+      );
+      delete process.env.TEST_CI;
     });
 
     it('should error if `--create` and `--update` flags are passed simultaneously', () => {
diff --git a/__tests__/cmds/versions/create.test.ts b/__tests__/cmds/versions/create.test.ts
index 9f8d1af33..765c5336e 100644
--- a/__tests__/cmds/versions/create.test.ts
+++ b/__tests__/cmds/versions/create.test.ts
@@ -15,10 +15,19 @@ describe('rdme versions:create', () => {
 
   afterEach(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(createVersion.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(createVersion.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(createVersion.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should error if no version provided', () => {
diff --git a/__tests__/cmds/versions/delete.test.ts b/__tests__/cmds/versions/delete.test.ts
index 6fc17e0dc..d27443335 100644
--- a/__tests__/cmds/versions/delete.test.ts
+++ b/__tests__/cmds/versions/delete.test.ts
@@ -1,4 +1,5 @@
 import nock from 'nock';
+import prompts from 'prompts';
 
 import DeleteVersionCommand from '../../../src/cmds/versions/delete';
 import APIError from '../../../src/lib/apiError';
@@ -14,10 +15,19 @@ describe('rdme versions:delete', () => {
 
   afterEach(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(deleteVersion.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(deleteVersion.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(deleteVersion.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should delete a specific version', async () => {
diff --git a/__tests__/cmds/versions/index.test.ts b/__tests__/cmds/versions/index.test.ts
index 47bf9e2b5..3c64ea5ff 100644
--- a/__tests__/cmds/versions/index.test.ts
+++ b/__tests__/cmds/versions/index.test.ts
@@ -1,6 +1,7 @@
 import type { Version } from '../../../src/cmds/versions';
 
 import nock from 'nock';
+import prompts from 'prompts';
 
 import VersionsCommand from '../../../src/cmds/versions';
 import getAPIMock from '../../helpers/get-api-mock';
@@ -36,10 +37,17 @@ describe('rdme versions', () => {
 
   afterEach(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(versions.run({})).rejects.toStrictEqual(
-      new Error('No project API key provided. Please use `--key`.')
-    );
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(versions.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(versions.run({})).rejects.toStrictEqual(new Error('No project API key provided. Please use `--key`.'));
+    delete process.env.TEST_CI;
   });
 
   it('should make a request to get a list of existing versions', async () => {
diff --git a/__tests__/cmds/versions/update.test.ts b/__tests__/cmds/versions/update.test.ts
index 2d55fa136..a45c7d0b7 100644
--- a/__tests__/cmds/versions/update.test.ts
+++ b/__tests__/cmds/versions/update.test.ts
@@ -15,10 +15,19 @@ describe('rdme versions:update', () => {
 
   afterEach(() => nock.cleanAll());
 
-  it('should error if no api key provided', () => {
-    return expect(updateVersion.run({})).rejects.toStrictEqual(
+  it('should prompt for login if no API key provided', async () => {
+    const consoleInfoSpy = jest.spyOn(console, 'info').mockImplementation();
+    prompts.inject(['this-is-not-an-email', 'password', 'subdomain']);
+    await expect(updateVersion.run({})).rejects.toStrictEqual(new Error('You must provide a valid email address.'));
+    consoleInfoSpy.mockRestore();
+  });
+
+  it('should error in CI if no API key provided', async () => {
+    process.env.TEST_CI = 'true';
+    await expect(updateVersion.run({})).rejects.toStrictEqual(
       new Error('No project API key provided. Please use `--key`.')
     );
+    delete process.env.TEST_CI;
   });
 
   it('should update a specific version object', async () => {
diff --git a/src/cmds/categories/create.ts b/src/cmds/categories/create.ts
index e18c78844..2019153ca 100644
--- a/src/cmds/categories/create.ts
+++ b/src/cmds/categories/create.ts
@@ -54,7 +54,7 @@ export default class CategoriesCreateCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { categoryType, title, key, version, preventDuplicates } = opts;
 
diff --git a/src/cmds/categories/index.ts b/src/cmds/categories/index.ts
index 050c7c440..933f9e444 100644
--- a/src/cmds/categories/index.ts
+++ b/src/cmds/categories/index.ts
@@ -18,7 +18,7 @@ export default class CategoriesCommand extends Command {
   }
 
   async run(opts: CommandOptions<{}>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { key, version } = opts;
 
diff --git a/src/cmds/changelogs/index.ts b/src/cmds/changelogs/index.ts
index 0b37e93dd..f63a3e377 100644
--- a/src/cmds/changelogs/index.ts
+++ b/src/cmds/changelogs/index.ts
@@ -42,7 +42,7 @@ export default class ChangelogsCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { dryRun, folder, key } = opts;
 
diff --git a/src/cmds/changelogs/single.ts b/src/cmds/changelogs/single.ts
index 5f9e7fd16..ebccc971c 100644
--- a/src/cmds/changelogs/single.ts
+++ b/src/cmds/changelogs/single.ts
@@ -41,7 +41,7 @@ export default class SingleChangelogCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { dryRun, filePath, key } = opts;
 
diff --git a/src/cmds/custompages/index.ts b/src/cmds/custompages/index.ts
index 3dd1bafe0..1ebebe172 100644
--- a/src/cmds/custompages/index.ts
+++ b/src/cmds/custompages/index.ts
@@ -42,7 +42,7 @@ export default class CustomPagesCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { dryRun, folder, key } = opts;
 
diff --git a/src/cmds/custompages/single.ts b/src/cmds/custompages/single.ts
index d2c5f7f5b..0922baabb 100644
--- a/src/cmds/custompages/single.ts
+++ b/src/cmds/custompages/single.ts
@@ -40,7 +40,7 @@ export default class SingleCustomPageCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { dryRun, filePath, key } = opts;
 
diff --git a/src/cmds/docs/edit.ts b/src/cmds/docs/edit.ts
index 859cfc1f8..24b66c1df 100644
--- a/src/cmds/docs/edit.ts
+++ b/src/cmds/docs/edit.ts
@@ -45,7 +45,7 @@ export default class EditDocsCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>): Promise<undefined> {
-    super.run(opts);
+    await super.run(opts);
 
     const { slug, key, version } = opts;
 
diff --git a/src/cmds/docs/index.ts b/src/cmds/docs/index.ts
index 9fe7cc9e0..9198b21d0 100644
--- a/src/cmds/docs/index.ts
+++ b/src/cmds/docs/index.ts
@@ -59,7 +59,7 @@ export default class DocsCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { dryRun, folder, key, version, cleanup } = opts;
 
diff --git a/src/cmds/docs/single.ts b/src/cmds/docs/single.ts
index da4ad3679..a13cd1aa2 100644
--- a/src/cmds/docs/single.ts
+++ b/src/cmds/docs/single.ts
@@ -42,7 +42,7 @@ export default class SingleDocCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { dryRun, filePath, key, version } = opts;
 
diff --git a/src/cmds/login.ts b/src/cmds/login.ts
index 883871f1c..43c8282cd 100644
--- a/src/cmds/login.ts
+++ b/src/cmds/login.ts
@@ -1,35 +1,14 @@
 import type { CommandOptions } from '../lib/baseCommand';
 
-import chalk from 'chalk';
-import config from 'config';
 import prompts from 'prompts';
-import isEmail from 'validator/lib/isEmail';
 
 import Command, { CommandCategories } from '../lib/baseCommand';
-import configStore from '../lib/configstore';
-import fetch, { handleRes } from '../lib/fetch';
-import { debug } from '../lib/logger';
-import promptTerminal from '../lib/promptWrapper';
+import loginFlow from '../lib/loginFlow';
 
 export type Options = {
   project?: string;
 };
 
-type LoginBody = {
-  email?: string;
-  password?: string;
-  project?: string;
-  token?: string;
-};
-
-function loginFetch(body: LoginBody) {
-  return fetch(`${config.get('host')}/api/v1/login`, {
-    method: 'post',
-    headers: { Accept: 'application/json', 'Content-Type': 'application/json' },
-    body: JSON.stringify(body),
-  });
-}
-
 export default class LoginCommand extends Command {
   constructor() {
     super();
@@ -50,63 +29,10 @@ export default class LoginCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     prompts.override(opts);
 
-    const { email, password, project } = await promptTerminal([
-      {
-        type: 'text',
-        name: 'email',
-        message: 'What is your email address?',
-        initial: configStore.get('email'),
-        validate(val) {
-          return isEmail(val) ? true : 'Please provide a valid email address.';
-        },
-      },
-      {
-        type: 'invisible',
-        name: 'password',
-        message: 'What is your password?',
-      },
-      {
-        type: 'text',
-        name: 'project',
-        message: 'What project are you logging into?',
-        initial: configStore.get('project'),
-      },
-    ]);
-
-    if (!project) {
-      return Promise.reject(new Error('No project subdomain provided. Please use `--project`.'));
-    }
-
-    if (!isEmail(email)) {
-      return Promise.reject(new Error('You must provide a valid email address.'));
-    }
-
-    return loginFetch({ email, password, project })
-      .then(handleRes)
-      .catch(async err => {
-        // if the user's login requires 2FA, let's prompt them for the token!
-        if (err.code === 'LOGIN_TWOFACTOR') {
-          debug('2FA error response, prompting for 2FA code');
-          const { token } = await promptTerminal({
-            type: 'text',
-            name: 'token',
-            message: 'What is your 2FA token?',
-          });
-
-          return loginFetch({ email, password, project, token }).then(handleRes);
-        }
-        throw err;
-      })
-      .then(res => {
-        configStore.set('apiKey', res.apiKey);
-        configStore.set('email', email);
-        configStore.set('project', project);
-
-        return `Successfully logged in as ${chalk.green(email)} to the ${chalk.blue(project)} project.`;
-      });
+    return loginFlow();
   }
 }
diff --git a/src/cmds/logout.ts b/src/cmds/logout.ts
index ebe0448f5..3ff0709e8 100644
--- a/src/cmds/logout.ts
+++ b/src/cmds/logout.ts
@@ -19,7 +19,7 @@ export default class LogoutCommand extends Command {
   }
 
   async run(opts: CommandOptions<{}>) {
-    super.run(opts);
+    await super.run(opts);
 
     if (configStore.has('email') && configStore.has('project')) {
       configStore.clear();
diff --git a/src/cmds/oas.ts b/src/cmds/oas.ts
index 0c623cc6b..4d676b649 100644
--- a/src/cmds/oas.ts
+++ b/src/cmds/oas.ts
@@ -18,7 +18,7 @@ export default class OASCommand extends Command {
   }
 
   async run(opts: CommandOptions<{}>) {
-    super.run(opts);
+    await super.run(opts);
 
     const message = [
       'This `oas` integration is now inactive.',
diff --git a/src/cmds/open.ts b/src/cmds/open.ts
index 4063b81cc..67b6ea984 100644
--- a/src/cmds/open.ts
+++ b/src/cmds/open.ts
@@ -25,7 +25,7 @@ export default class OpenCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const project = configStore.get('project');
     Command.debug(`project: ${project}`);
diff --git a/src/cmds/openapi/index.ts b/src/cmds/openapi/index.ts
index f9ac8d23d..f6b9ff9ff 100644
--- a/src/cmds/openapi/index.ts
+++ b/src/cmds/openapi/index.ts
@@ -91,7 +91,7 @@ export default class OpenAPICommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { dryRun, key, id, spec, create, raw, useSpecVersion, version, workingDirectory, update } = opts;
 
diff --git a/src/cmds/openapi/reduce.ts b/src/cmds/openapi/reduce.ts
index bce67d538..601f50788 100644
--- a/src/cmds/openapi/reduce.ts
+++ b/src/cmds/openapi/reduce.ts
@@ -45,7 +45,7 @@ export default class OpenAPIReduceCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { spec, workingDirectory } = opts;
 
diff --git a/src/cmds/openapi/validate.ts b/src/cmds/openapi/validate.ts
index 6cc8ad90c..8324c420a 100644
--- a/src/cmds/openapi/validate.ts
+++ b/src/cmds/openapi/validate.ts
@@ -38,7 +38,7 @@ export default class OpenAPIValidateCommand extends Command {
   }
 
   async run(opts: CommandOptions<Options>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { spec, workingDirectory } = opts;
 
diff --git a/src/cmds/versions/create.ts b/src/cmds/versions/create.ts
index f8d9e7f04..068443927 100644
--- a/src/cmds/versions/create.ts
+++ b/src/cmds/versions/create.ts
@@ -47,7 +47,7 @@ export default class CreateVersionCommand extends Command {
   }
 
   async run(opts: CommandOptions<VersionCreateOptions>) {
-    super.run(opts);
+    await super.run(opts);
 
     let versionList;
     const { key, version, fork, codename, main, beta, isPublic } = opts;
diff --git a/src/cmds/versions/delete.ts b/src/cmds/versions/delete.ts
index 3025ff9b1..fc1dc799d 100644
--- a/src/cmds/versions/delete.ts
+++ b/src/cmds/versions/delete.ts
@@ -28,7 +28,7 @@ export default class DeleteVersionCommand extends Command {
   }
 
   async run(opts: CommandOptions<{}>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { key, version } = opts;
 
diff --git a/src/cmds/versions/index.ts b/src/cmds/versions/index.ts
index 05bf7b2cb..cd22a51fd 100644
--- a/src/cmds/versions/index.ts
+++ b/src/cmds/versions/index.ts
@@ -37,7 +37,7 @@ export default class VersionsCommand extends Command {
   }
 
   async run(opts: CommandOptions<{}>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { key, version } = opts;
 
diff --git a/src/cmds/versions/update.ts b/src/cmds/versions/update.ts
index 80f84199c..4c0b808f8 100644
--- a/src/cmds/versions/update.ts
+++ b/src/cmds/versions/update.ts
@@ -46,7 +46,7 @@ export default class UpdateVersionCommand extends Command {
   }
 
   async run(opts: CommandOptions<VersionUpdateOptions>) {
-    super.run(opts);
+    await super.run(opts);
 
     const { key, version, newVersion, codename, main, beta, isPublic, deprecated } = opts;
 
diff --git a/src/cmds/whoami.ts b/src/cmds/whoami.ts
index fec952000..d1d075fbd 100644
--- a/src/cmds/whoami.ts
+++ b/src/cmds/whoami.ts
@@ -20,7 +20,7 @@ export default class WhoAmICommand extends Command {
   }
 
   async run(opts: CommandOptions<{}>) {
-    super.run(opts);
+    await super.run(opts);
 
     if (!configStore.has('email') || !configStore.has('project')) {
       return Promise.reject(new Error(`Please login using \`${config.get('cli')} login\`.`));
diff --git a/src/lib/baseCommand.ts b/src/lib/baseCommand.ts
index f475ef3ef..1152ea63b 100644
--- a/src/lib/baseCommand.ts
+++ b/src/lib/baseCommand.ts
@@ -3,8 +3,10 @@ import type commands from '../cmds';
 import type { CommandLineOptions } from 'command-line-args';
 import type { OptionDefinition } from 'command-line-usage';
 
+import configstore from './configstore';
 import isCI from './isCI';
 import { debug, info, warn } from './logger';
+import loginFlow from './loginFlow';
 
 export type CommandOptions<T> = T & {
   key?: string;
@@ -86,13 +88,20 @@ export default class Command {
    */
   args: OptionDefinition[];
 
-  run(opts: CommandOptions<{}>): Promise<string> {
+  async run(opts: CommandOptions<{}>): Promise<string> {
     Command.debug(`command: ${this.command}`);
     Command.debug(`opts: ${JSON.stringify(opts)}`);
 
     if (this.args.some(arg => arg.name === 'key')) {
       if (!opts.key) {
-        throw new Error('No project API key provided. Please use `--key`.');
+        if (isCI()) {
+          throw new Error('No project API key provided. Please use `--key`.');
+        }
+        info("Looks like you're missing a ReadMe API key, let's fix that! 🦉", false);
+        const result = await loginFlow();
+        info(result, false);
+        // eslint-disable-next-line no-param-reassign
+        opts.key = configstore.get('apiKey');
       }
     }
 
diff --git a/src/lib/createGHA/index.ts b/src/lib/createGHA/index.ts
index c929137d7..ef922081a 100644
--- a/src/lib/createGHA/index.ts
+++ b/src/lib/createGHA/index.ts
@@ -16,7 +16,7 @@ import { checkFilePath, cleanFileName } from '../checkFile';
 import configstore from '../configstore';
 import { getPkgVersion } from '../getPkgVersion';
 import isCI from '../isCI';
-import { debug } from '../logger';
+import { debug, info } from '../logger';
 import promptTerminal from '../promptWrapper';
 
 import yamlBase from './baseFile';
@@ -192,24 +192,12 @@ export default async function createGHA(
     }
   }
 
-  /**
-   * The reason we're using console.info() in these lines as opposed to
-   * our logger is because that logger has some formatting limitations
-   * and this function doesn't ever run in a GitHub Actions environment.
-   * By using `info` as opposed to `log`, we also can mock it in our tests
-   * while also freely using `log` when debugging our code.
-   *
-   * @see {@link https://github.com/readmeio/rdme/blob/main/CONTRIBUTING.md#usage-of-console}
-   */
-  // eslint-disable-next-line no-console
-  if (msg) console.info(msg);
+  if (msg) info(msg, false);
 
   if (opts.github) {
-    // eslint-disable-next-line no-console
-    console.info(chalk.bold("\n🚀 Let's get you set up with GitHub Actions! 🚀\n"));
+    info(chalk.bold("\n🚀 Let's get you set up with GitHub Actions! 🚀\n", false));
   } else {
-    // eslint-disable-next-line no-console
-    console.info(
+    info(
       [
         '',
         chalk.bold("🐙 Looks like you're running this command in a GitHub Repository! 🐙"),
@@ -220,7 +208,8 @@ export default async function createGHA(
         '',
         `✨ This means it will run ${chalk.italic('automagically')} with every push to a branch of your choice!`,
         '',
-      ].join('\n')
+      ].join('\n'),
+      false
     );
   }
 
diff --git a/src/lib/logger.ts b/src/lib/logger.ts
index f03985776..f3d1b9135 100644
--- a/src/lib/logger.ts
+++ b/src/lib/logger.ts
@@ -12,7 +12,6 @@ const debugPackage = debugModule(config.get('cli'));
 
 /**
  * Wrapper for debug statements.
- * @param {String} input
  */
 function debug(input: string) {
   /* istanbul ignore next */
@@ -22,7 +21,6 @@ function debug(input: string) {
 
 /**
  * Wrapper for warn statements.
- * @param {String} input
  */
 function warn(input: string) {
   /* istanbul ignore next */
@@ -33,11 +31,14 @@ function warn(input: string) {
 
 /**
  * Wrapper for info/notice statements.
- * @param {String} input
+ * @param {Boolean} includeEmojiPrefix whether or not to prefix
+ * the statement with this emoji: ℹ️
  */
-function info(input: string) {
+function info(input: string, includeEmojiPrefix = true) {
   /* istanbul ignore next */
   if (isGHA() && process.env.NODE_ENV !== 'test') return core.notice(input);
+  /* istanbul ignore next */
+  if (!includeEmojiPrefix) return console.info(input); // eslint-disable-line no-console
   // eslint-disable-next-line no-console
   return console.info(`ℹ️  ${input}`);
 }
diff --git a/src/lib/loginFlow.ts b/src/lib/loginFlow.ts
new file mode 100644
index 000000000..21a9392c4
--- /dev/null
+++ b/src/lib/loginFlow.ts
@@ -0,0 +1,86 @@
+import chalk from 'chalk';
+import config from 'config';
+import isEmail from 'validator/lib/isEmail';
+
+import configStore from './configstore';
+import fetch, { handleRes } from './fetch';
+import { debug } from './logger';
+import promptTerminal from './promptWrapper';
+
+type LoginBody = {
+  email?: string;
+  password?: string;
+  project?: string;
+  token?: string;
+};
+
+function loginFetch(body: LoginBody) {
+  return fetch(`${config.get('host')}/api/v1/login`, {
+    method: 'post',
+    headers: { Accept: 'application/json', 'Content-Type': 'application/json' },
+    body: JSON.stringify(body),
+  });
+}
+
+/**
+ * The prompt flow for logging a user in and writing the credentials to
+ * `configstore`. This is a separate lib function because we reuse it both
+ * in the `login` command as well as any time a user omits an API key.
+ * @returns A Promise-wrapped string with the logged-in user's credentials
+ */
+export default async function loginFlow() {
+  const { email, password, project } = await promptTerminal([
+    {
+      type: 'text',
+      name: 'email',
+      message: 'What is your email address?',
+      initial: configStore.get('email'),
+      validate(val) {
+        return isEmail(val) ? true : 'Please provide a valid email address.';
+      },
+    },
+    {
+      type: 'invisible',
+      name: 'password',
+      message: 'What is your password?',
+    },
+    {
+      type: 'text',
+      name: 'project',
+      message: 'What project are you logging into?',
+      initial: configStore.get('project'),
+    },
+  ]);
+
+  if (!project) {
+    return Promise.reject(new Error('No project subdomain provided. Please use `--project`.'));
+  }
+
+  if (!isEmail(email)) {
+    return Promise.reject(new Error('You must provide a valid email address.'));
+  }
+
+  return loginFetch({ email, password, project })
+    .then(handleRes)
+    .catch(async err => {
+      // if the user's login requires 2FA, let's prompt them for the token!
+      if (err.code === 'LOGIN_TWOFACTOR') {
+        debug('2FA error response, prompting for 2FA code');
+        const { token } = await promptTerminal({
+          type: 'text',
+          name: 'token',
+          message: 'What is your 2FA token?',
+        });
+
+        return loginFetch({ email, password, project, token }).then(handleRes);
+      }
+      throw err;
+    })
+    .then(res => {
+      configStore.set('apiKey', res.apiKey);
+      configStore.set('email', email);
+      configStore.set('project', project);
+
+      return `Successfully logged in as ${chalk.green(email)} to the ${chalk.blue(project)} project.`;
+    });
+}