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Outlook 2003 cannot send multiple messages

With Outlook 2003:

When I have multiple messages in Outbox, and click "Send/Receive", only one message is sent, and then a "send" error occurs.

For instance, sending through an SMTP server that requires SSL, the error 0x800ccc7d occurs, which refers to server not supporting SSL (this cannot be - sending just one message works fine).

I tried with other SMTP servers (without SSL) and still only one message is sent out of those in the Outbox. Also, I set the antivirus not to scan sent messages but no fix.

Any suggestions?
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In your account setup, double check the following:

1. In the Outgoing Server tab that you have set Authentication properly. It probably needs to be enabled.

2. In the Advanced tab that you use the proper ports:  995/SSL  465 or 587 / SSL or TLS. These settings need to come from the ISP.

3. In the general account set up area that both POP3 and SMTP addresses are correct.

Then, if you have verified all the settings are correct, do an Office Repair. Go to Control Panel, click on Office and select Change/Repair.

There are 3 service packs for Office. Make sure all 3 service packs have been applied and Office is fully patched.

.... Thinkpads_User
Another thing to consider is that you may have a corrupt Mail profile.

1. Make a sure and certain backup of your PST files (ALL) in a non-Outlook location.
2. Make sure you know how to recreate your mail account(s). Document them.
3. Close Outlook.
4. Open Control Panel, Mail, and delete the Outlook Profile.
5. Restart but do not start Outlook.
6. Open Control Panel, Mail and make a new Outlook Profile.
7. Set it up and import your email from the backup location. Your email may show up by itself and if it did, that's fine.

.... Thinkpads_User
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Did all, new profile too, sp3, time ago. No difference. Sending just one message works fine! Then I set it to "send immediately" and so I cannot get more than one message in Outbox. But I cannot make a change to that message either... it's gone immediately. Anyway, the point is I'd like to fix my Outlook.

Any other suggestions?
If you have done everything above:

1. You may have an operating system corruption.  Make a new Windows User Profile (Account) and set up Outlook temporarily in the new profile. Test the sending.

Do you still have an issue in the new Windows Profile?

2. You may have a virus. Check carefully for viruses with your own suite and then use Malwarebytes (download the free trial virus checker).

3. I do assume internet is working properly. Please let us know if not.

.... Thinkpads_User
no-no, this machine is clean, checked with various/multiple anti malware tools, has tons of apps that never skip a beat. Problem has been there for a year - in the meantime, no other issues. It's just Outlook for certain - has anyone else encountered this issue? What did you do about it?
It's just Outlook for certain   NO. Outlook 2003 works perfectly. I used it for years and I still have it running on an XP Pro machine.

If you are using Outlook 2003 (dead) on XP (also dead), it will work fine. I have it running.

If you are using Outlook 2003 on a newer OS like Windows 7, it is not supported and in this case you would need to upgrade it.

But it is not an Outlook issue.

.... Thinkpads_User
In addition to the above, I asked you to try Outlook in a new (test) Windows User Account (Profile). Did you try that?  And what happened?

.... Thinkpads_User
no difference
OK.  So then what operating system are you using?

If XP, then the system is hosed and needs to be rebuilt (you have tried everything else).

If Vista, Seven, or Eight, you need to upgrade Office.

... Thinkpads_User
Experts, has anyone encountered this issue?
You keep asking questions,  Please answer the questions above and then we can help you.

..... Thinkpads_User

Now it looks to me that your XP system is damaged. Why?  All the thing tried, all the settings and repair, and the big two:  new Outlook Profile and new XP Windows User Profile have not worked.

The only next step left (before reinstalling XP) is to run System File Checker. Start up with an administrative command profile, open Command, and run SFC /SCANNOW. In XP, this will ask you for your XP install DVD. Provide it, and allow to complete. Restart and test.

Two things about SFC in XP:

1. You do need the install DVD.
2. There is a big risk it will not finish properly.

Therefore, you must back up your system before ever trying SFC on XP. Make sure you have your documents, files and photos, your favourites in IE or browser, and ALL your PST files (main plus archives).

Should you get this far without success, then you need to reinstall XP. Outlook is not your issue. I have run Outlook 2003 for years without problem on XP.

.... Thinkpads_User
One last thing to check in Outlook is the PST file size. 2Gb is maximum and too big for comfort. You can always try Archiving to bring the PST down to 1Gb.

However, I think if file size were the issue that receiving would also be a problem.

.... Thinkpads_User
This machine has a large number of apps/tools that never skip a beat.
Thank you for your opinion. Let's allow others express an opinion too.

So yes, with "Send immediately" checked, all is well. But without, when more messages accumulate in Outbox, from multiple accounts, Outlook can send only one message - then an error occurs. Pressing Send/Receive repeatedly would eventually send all messages. Some Outlook data/config file probably got corrupted (?).

Outlook experts, anyone? Thanks for helping.
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For those having Outlook problems, there are a number of excellent Outlook troubleshooting docs by Microsoft - here is one of them:
(Troubleshooting Outlook Crashes)
My own comment as solution because I found the solution there was no other comment that helped me in finding the solution.