Since Google removed "less secure app access", you cannot sign in to a third-party sending tool with your normal Gmail password. You need an app password — a 16-character code specifically for SMTP/IMAP. It takes about three minutes.
Before you start: enable 2-Step Verification
App passwords only exist once 2-Step Verification is turned on.
- Open your Google Account Security page.
- Under "How you sign in to Google", select 2-Step Verification and follow the prompts (you will confirm a phone number).
If you use a Google Workspace company account and cannot find these options, your workspace administrator must first allow 2-Step Verification in the Admin console.
Generate the app password
- Go to myaccount.google.com/apppasswords.
- Give the app a name such as
AutoAiMailand click Create. - Google shows a 16-character code (shown in four groups). Copy it — spaces are optional when pasting.
Connect it inside AutoAiMail
- Choose Gmail from the provider list.
- Enter your full Gmail address and paste the 16-character app password as the SMTP/IMAP password.
- AutoAiMail auto-fills
smtp.gmail.com:465andimap.gmail.com:993, verifies the login immediately and reports success or the precise fix.
Common problems
- "The setting you are looking for is not available for your account" — 2-Step Verification is not enabled yet, or a Workspace policy blocks it.
- Authentication failed 535 — you used your normal login password instead of the app password, or 2FA is off.
- Still failing? Prefer one-click Sign in with Google (OAuth) when available — no password handling at all and tokens refresh automatically.
App passwords are revocable any time from the same Google page, so rotating credentials when a teammate leaves is a one-click action.