I can’t send HTML email or attachments; they get stuck in my outbox. What do I need to do?

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.