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I'm not leaning towards Microsoft Outlook being the problem here. I think it's something related to your ISP or email service and the size of the emails you are attempting to send.

I'm running the following software: Windows Vista Home Premium Version 6 SP 2 Build 6002, Microsoft Outlook 2003 SP3 Professional Edition, on a Dell Inspiron 530 with 3 GB of RAM. I can receive both plain text and HTML email messages with attachments in Microsoft Outlook 2003. When I reply-to or create a new HTML email, the message remains in the Outbox and is sometimes sent multiple times. If I convert to plain text or create a new plain text email, the email is sent and goes correctly to the sent folder. If I attach a document to plain text email it remains in the Outbox and it is not sent. I've reloaded Microsoft Outlook software. Can I correct this situation or do I just to move on to other email software?

In this excerpt from Answercast #66, I look at various reasons why email might not be sending correctly.

Email won't send

I'm not convinced that this is actually an email software related issue.

The symptoms that you describe are symptoms that I often see when your email service is rejecting your email for either taking too long to send or for being too large.

Email too large

Now, it is the case that an HTML email, containing the same message, is going to be larger than the plain text email message that contains the same information. I wouldn't expect it to be so dramatically large that it should cause your ISP, or your email service provider, to hiccup on it; to say that it takes too long to send. But those are the kinds of things I would look at; especially because even just adding an attachment to your plain text email message is causing you this problem.

So what I would do, instead of suspecting Outlook, I would first see who your email provider is. Ask them for assistance on this. It is possible that there is something that is set incorrectly, or something that is specific to your email service that might be causing this kind of behavior.

Unfortunately, (I don't know who your provider is) but I will say that the answer you're going to get from them is going to vary dramatically. There are going to be some IPS that are going to immediately say, "it can't possibly be our problem." But if you've got a good ISP they'll, hopefully, help you diagnose this a little bit, and come to some kind of resolution.

Try a different program

If not, you can certainly fire up a different email program. With Vista you've got Windows Mail there for you.

You don't have to move to it to try it out. You can certainly fire it up, and configure it for your email account. See if using it makes a difference of any sort. My suspicion is that it might not, but it's really hard to say.

Repair install

The other thing that I normally suggest in this case is that you either run a repair install, or a reinstall of the entire Microsoft Office. You've indicated that you reloaded the Microsoft Outlook software. I'm not exactly sure what steps you took to do that but there are two specific approaches that I typically recommend in order to accomplish that.

If you haven't done either of these, I'd recommend trying those as well. That is whats called is called a repair install:

  • When you go to Control Panel, in Programs, you'll find an entry there for "Microsoft Office."

  • If you right-click on it and then click on Change, what it will do is it will actually fire up the setup program.

  • One of the options in the setup program will be to "repair the existing installation" of Microsoft Office.

That will include Microsoft Outlook. That's one thing to try.

Uninstall and reinstall

The other, more radical, approach (rather than just installing it on top of your existing installation) would be to uninstall Microsoft Office completely and then reinstall it from scratch.

Naturally before you do that, you're going to want to back up your data; specifically your PST files. That's one way to pretty much guarantee that Microsoft Office gets reset to its default state.

Like I said, I'm not leaning towards Microsoft Outlook being the problem here. I really do think it's something related to your ISP or email service but it certainly is something that you can rule out by doing these steps.

Article C5978 - October 31, 2012 « »

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Leo Leo A. Notenboom has been playing with computers since he was required to take a programming class in 1976. An 18 year career as a programmer at Microsoft soon followed. After "retiring" in 2001, Leo started Ask Leo! in 2003 as a place for answers to common computer and technical questions. More about Leo.

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3 Comments
John O'Meara
November 2, 2012 8:33 AM

It may be that the HTML email messages actually are very large. Some 'signatures' attached to emails contain several images. If the images are not sized properly, they can take up megabytes. (Leo talked about graphic file sizing in a recent Answercast). If the ISP is rejecting supersized messages, resizing the images would be one immediate strting point.

bob price
November 2, 2012 9:32 AM

This happens to me a lot. Mine are just ordinary emails, text only, no attachments. This did not happen with hotmail, but does in the newer Outlook,com. I will send or reply to a dozen emails, and then check the Draft folder. Sure enough one or two will be stuck in there.

Frank Hermann
November 12, 2012 1:32 AM

Sounds very familiar, as this typically happens when port 25 is blocked by the ISP. The solution is to use an SMTP server. It took a while for me to figure this out, while staying in Asia. You can read more about this on http://timreviews.com/cant-send-mails

Frank

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