Member Avatar for mugomukwasi

I have a problem that I am currently experiencing, Emails remain stuck in outbox after sending them. My server (OS) is Windows 2000 Server (version 4.0) and it uses Microsoft Outlook. This is happening to every client on my domain and its not one user who is having this problem. My server uses POP3.

Those who have once exprienced the same problem can you assist please.

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For a domain‑wide Outlook problem where every client’s message stays in the Outbox, treat this as a server or network issue first (not a single damaged mailbox). pointed to an Outlook Express fix, which is fine for OE, but Outlook + a central POP3/SMTP server usually needs a different checklist. The steps below are practical, ordered from quickest checks to deeper server troubleshooting.

  • Quick client checks: confirm Outlook is “Online” (not Work Offline) and try sending a small plain text test message with no attachments. Start Outlook in safe mode to rule out add‑ins:

    outlook.exe /safe

  • Connectivity tests: verify the client can reach the SMTP port on the mail server. From a client run:

    telnet mailserver.example.com 25

    If telnet fails, the problem is network/firewall/port blocking (ISP or perimeter firewall).

  • Server checks: on the Windows 2000 mail server ensure the SMTP service is running and examine the SMTP queue (IIS SMTP default queue: C:\Inetpub\mailroot\Queue) and server event logs for delivery errors. Look for DNS resolution failures, smarthost errors, or authentication failures.

  • Other common causes: outbound SMTP authentication required but not enabled in clients, ISP blocking port 25 (use 587 with auth), antivirus or gateway mail scanning interfering, or very large attachments.

Recommended fixes (in order): restart the SMTP service, temporarily disable AV mail scanning for a quick test, enable SMTP authentication or switch to authenticated submission (port 587), try resending a small test message, and create a fresh Outlook profile if a single client still fails. If the issue persists across the domain, collect SMTP logs and server event logs and involve the ISP or hosting provider. Note: Windows 2000 is end of life; consider migrating to a supported mail platform for long‑term stability and security.

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Member Avatar for sparkax

Try this
This works in Outlook Express -maybe in Outlook?

Close OutLook
Search for outbox.dbx
Rename old_outbox.dbx
Restart outlook and it will create a new outbox.dbx file.
After closing outlook - delete old_outbox.dbx if you wish.

Member Avatar for sparkax

I don't think the above will apply to Outlook.
try this link

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