Not sending mails with attachments (Imap Gmail)

I've only Imap-Gmail accounts in my Apple Mail, and using it for almost a year without any problems. But since a couple of weeks, most of the time I'll send an email with an attachment in it. I'll get the Pop-Up window that the mail can not be sent, and that I can choose another mailserver to send the mail. When I check my connection, there is not a problem. But the mail is still standing in my Outgoing Mail and is not sending.
Can anyone help?

I was troubleshooting my own issue noted above and tried to send the attachments via gmail's web interface (bypassing Apple Mail). This time, gmail provided an error message stating that the file contained a virus.
Since it was a zip of several Word docs, I saved them as PDFs and then rezipped, and Apple Mail sent them off like a champ.
Evidently, Mail does not have a method for relaying the precise nature of the error message that gmail sends (in this case that the attachment had what gmail thought was a virus). This would be a prime area for some software developers to tackle on a future version of Mail.
By the way, the files almost certainly do not contain viruses; they are extremely old Word Docs that have been on my successive Mac hard drives for at least 9 years. Too old a format for gmail to recognize?
Hope this helps someone who may be having the same trouble.

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hey, apple mail serice is sending mail but not sending mail with files atteched.
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Hmm. Looking at the Apple UK support site, it shows a yellow dot for .Mac mail, but says the issue is with incoming mail:
http://www.apple.com/uk/support/dotmac/
Not sure if that has anything to do with it or if there are other issues.
There's also some info at:
http://www.apple.com/uk/support/dotmac/mail/
Interestingly enough, they suggest using your ISP's SMTP server for outgoing mail:
http://docs.info.apple.com/article.html?path=Dotmac/Mail/en/mac14.html
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Hello,
I can't send mails anymore, I have been able to send some without any attachments (i.e. reply doesn't work as it automatically attaches the original text). This started 3 days ago. Also, my mail doesn't seem to recognize powerpoint and word docs., but I a know the people who have send me such files do not have VISTA. When I choose "open with" then it works. So I have 2 problems, one being moe urgent then the other.
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thank you all!!!

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Hi,
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I have got a problem sending mail with attachments...
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Thanks in advance

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Out of the blue I cannot send e-mails with attachments (any kind). Mail without attachments go out without problems.
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I have configured my ME account to Apple Mail. When I send an email with first some text, then i add an picture under the text, and after the picture i add some more text. Then i send the mail to someone.
When that person opens the mail in Outlook on Windows for example, the first text that i typed above the picture is visible in the mail, the picture is added as an jpg attachment, but the text that i typed under the picture is always added in a HTM file
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I was troubleshooting my own issue noted above and tried to send the attachments via gmail's web interface (bypassing Apple Mail). This time, gmail provided an error message stating that the file contained a virus.
Since it was a zip of several Word docs, I saved them as PDFs and then rezipped, and Apple Mail sent them off like a champ.
Evidently, Mail does not have a method for relaying the precise nature of the error message that gmail sends (in this case that the attachment had what gmail thought was a virus). This would be a prime area for some software developers to tackle on a future version of Mail.
By the way, the files almost certainly do not contain viruses; they are extremely old Word Docs that have been on my successive Mac hard drives for at least 9 years. Too old a format for gmail to recognize?
Hope this helps someone who may be having the same trouble.

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Regards,
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** Message: smtp-client-session.vala:80: Unable to QUIT: Error writing data to TLS socket: The specified session has been invalidated for some reason.
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Perhaps the mail server has a size limit that it allows. Might try a free web service and see if that will work for those attachments.

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Not sending mails with attachments (Imap Gmail)

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