Member Avatar for idaryl

Up until 5 days ago Outlook 2011 on my iMac was working fine -but now it recieves emails but I cannot send them - all it does is save them as drafts.

I have it setup so it receives and sends from my (imap) gmail account (as I said it was fine until a few days ago). *I changed nothing - no reason to.

So searching the web produced a lot of "change the settings to this or that" but none of those remedies worked.

Has this happened to anyone, is there a fix for this? or does anyone know how to get Outlook running again - I use it for my business

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Short, practical troubleshooting checklist for the “receives but won’t send (saved to Drafts)” symptom reported by . This builds on ’s prompt-to-test and ’s identity-rebuild idea while adding SMTP/Gmail-specific checks and isolation steps.

  • Reproduce & record the failure: use Outlook’s connection/test tools and note the exact SMTP error text or status code. That text is the single most useful diagnostic artifact.
  • Basic client state: confirm Outlook is online (not in Work Offline) and that no message is stuck in an Outbox queue.
  • SMTP configuration (common failure point): outgoing server should be smtp.gmail.com, authentication must use the full Gmail address and password, and encryption should be TLS on port 587 (or SSL on 465). Try both ports and ensure “outgoing server requires authentication” is enabled.
  • Account security rules at the provider: Gmail can block older clients that use basic auth. If the account has 2‑step verification, an app‑specific password must be used. If Google is blocking the client for security reasons, either allow access via the account security settings (if that option still exists) or use an app password / a client that supports modern OAuth2. This matches ’s point that external changes can appear without local changes.
  • Local credentials & profile: clear any saved Outlook/Gmail password from the Mac keychain and force Outlook to re‑prompt. If the account works in another client (Apple Mail or Thunderbird) but not in Outlook, rebuild or recreate the Outlook identity as suggested. Creating a fresh Outlook account/profile first is a low‑risk test.
  • Isolation: try sending from Gmail web or a phone app. If those can send, the problem is client-side; if they cannot, the problem is account/security side. Also try a different network (tether mobile) in case a router/ISP blocks SMTP ports.

Useful next artifacts for deeper help: the exact SMTP/server error lines, the outgoing server host/port/auth settings in Outlook, and whether the Gmail account uses 2‑step verification. Long term: consider moving to a mail client that supports OAuth2 since Outlook 2011 predates modern auth changes.

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Member Avatar for Reverend Jim

In the accounts settings (where you enter the connection info) there should be a Test Connection button. What happens when you click it?

Member Avatar for Subbu_2

is it just for iMac?

Member Avatar for rma

Before you click on Outlook, hold down the alt key then click on Outlook. It will bring up the idenity box. Highlight your identy and then click on the "rebuild" button. This hopefully will fix any problems you have. The other thing you can do is add a second identy and see if you can send from that one. Your iMac is not the problem this sounds like a software issue.

Richard M Abaid
Macintosh Consultant

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