Email Isn't Sending: Diagnostic Walkthrough

You hit Send on a status update, an award letter, or a workflow email, and something went wrong. Maybe the recipient is on the phone telling you they never got it. Maybe you saw a red error toast and have no idea what it meant. Maybe the button just sat there and you are not sure if it went out twice. That is what this article is about.

Every email AwardLettr sends goes through one of three routes: your connected Gmail or Microsoft 365 account, our default sender (AWS SES), or a transactional path for things like booking links. Each route has its own failure modes, and the Email Log records the outcome of every attempt with the exact provider, recipient, state, and error. Most email problems are an expired OAuth token, an attachment that crossed a size limit, or a recipient mail server quietly quarantining the message. They look the same from the outside and are very different fixes.

Walk the decision tree below from the top. Pick the description that matches what you saw and the resolution will land you on the right next step. If you go through it and you still cannot explain what happened, copy the relevant row from the Email Log and message support. We can usually tell you what is going on in one reply.

Email problems are noisy. The fix usually is not. Walk the decision tree below from the top, pick the description that matches what you saw, and the resolution will land you on the right next step.

Diagnostic decision tree

When to use the fallback picker

When your primary provider fails (OAuth expired, attachment too large, tenant policy block), AwardLettr now offers a one-click fallback to send via AwardLettr default email (SES). You will see this option on the send dialog after a failure. It is fine to use — the email still references your appraisal and goes to the same recipient. The only difference is the From address.