Mail doesn't send to certain e-mail addresses, receiving seems ok

I am using the latest version of the Apple Mail application under Leopard (with all updates downloaded). About a month ago I e-mailed a friend from my home account and unusually didn’t get a reply. I then e-mailed again a few weeks after, again no reply. After a phone conversation found out she didn’t receive either of my mails. This prompted many test e-mails, the outcome of which was the following:
1 - Was able to receive my friend’s e-mails, but if I replied using Apple mail (hitting the reply button), my reply never got back to her.
2 - Was able to send to and receive my friend’s e-mails using MS outlook from my place of work using a PC and my work e-mail account. No problems.
3 - Was able to send and receive to my work account from my home account using Apple Mail, no problems.
4 - Was able to send and receive my friend e-mails from my home account, using web mail rather than using Apple Mail.
5 - Could no longer e-mail my wife using the Apple Mail (and she could not e-mail me), we both use the same ISP. However using web mail rather than Apple Mail we could still send and receive e-mails from each other.
6 - Phoned my ISP, my account seems to be ok, which was also confirmed by using webmail as described in the previous two points.
7 - Other than the regular Apple updates the Mail app is the same client I have been using since I got my new Mac last October. I didn’t appear to have any problems until about a month ago and have made no changes to settings etc.
8 - When I do attempt to send e-mails to my wife or friend, I get the usual whooshing sound and a progress bar to show that the mail has been sent. The outbox is empty and the mail appears in the sent box, but never arrives to its destination. No error messages or e-mail bounce backs, nothing.
9 - Downloaded and installed Thunderbird, all the problems seem to go away – I can now send and receive e-mails from both my wife and friend.
It’s a bit weird that Apple Mail seems to have taken an aversion to sending mail to some particular e-mail addresses. Unless someone can explain what is going on here, I think that this is a serious problem. As I’ve mentioned, there is no hint that Apple Mail is not sending e-mail, as far as I was concerned e-mails were leaving my Mac. Has anyone experienced something similar? Is there an easy fix?

I just did a quick test in InDesign CC and my one worked. Maybe you should delete the button and redo it.
By the way on a slightly different matter, do you know that to enable users to complete the form and store it on their computer using Acrobat Reader, you need to enable the form as follows:
Open the form in Acrobat XI and then:
File > Save As Other > Reader Extended PDF > Enable More Tools (includes for fill-in & save). . . Your users will be able to fill in the form and save it (assuming they have the later versions of Acrobat Reader).
Make sure you keep a copy of your original PDF with a different file name as once you've created a Reader Enabled PDF Form you can't change it.

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Hi. We noticed that the troubleshooting information was missing from these questions. In order to better investigate this issue, we may need to request a little more non-personal information.
Please add the troubleshooting information to your post as well as the results of the following troubleshooting steps:
* [https://support.mozilla.org/kb/use-troubleshooting-information-page-fix-firefox#w_accessing-the-troubleshooting-information-page Finding the Troubleshooting information]
*Does Thunderbird work in TB Safe mode (see [http://mzl.la/1k5DWjq Thunderbird Safe Mode])?
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*Who is the internet provider?
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Hi,
I am trying to involve someone familiar with this topic to further look at this issue.
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Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Subscriber Support, contact
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