Requesting help solving a "Cannot Send Mail" issue. Sending the message content to the server failed. Running OS X 9.5. Problem seemed to start after the last security upgrade 4-14-2015

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Level 1

8 points

Requesting help solving a "Cannot Send Mail" issue. Sending the message content to the server failed. Running OS X 9.5. Problem seemed to start after the last security upgrade 4-14-2015

I am having mail issues with my 15" (early 2011) MacBook Pro. Processor speed 2 GHz Intel Core i7. Memory has 4 GB 1333 MHz DDR3. Storage capacity 500 GB with 419 available. Running OS 10.9.5. Mail version 7.3.

I am getting the pop up box message: Cannot Send Mail - Sending the message content to the server failed. This pops up every time I open my mail. Just started since the last security update of April 14, 2015 Version 1.0. I have not tried anything other than researching what that message means. I don't think I have changed anything that would have caused the problem.

Thanks for any help that you can provide that will fix this issue.

Chris

MacBook Pro (15-inch Early 2011), OS X Mavericks (10.9.5), null

Posted on Apr 20, 2015 12:44 PM

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Answer 1

Linc Davis

Level 10

209,547 points

Apr 20, 2015 4:00 PM in response to tacomaman

If you can’t send or receive email on your Mac - Apple Support

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Answer 2

tacomaman Author

Level 1

8 points

Apr 20, 2015 4:21 PM in response to Linc Davis

No problems receiving mail. I have sent and had confirmed receipt of mail. Connection Doctor shows no problem connecting to the servers.

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Answer 3

Linc Davis

Level 10

209,547 points

Apr 20, 2015 4:24 PM in response to tacomaman

From the Mail menu bar, select

Window ▹ Connection Doctor

Look for the disused SMTP (outgoing mail) account in the window that opens. Double-click it. Another window will open, showing a list of all the outgoing mail accounts. The unwanted one will be selected. Click the minus-sign button to delete it, then click OK.

If there's more than one unwanted account, repeat.

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Answer 4

tacomaman Author

Level 1

8 points

Apr 22, 2015 7:26 PM in response to Linc Davis

I have done as you suggested and selected a disused SMTP account(not sure I had a disused one however) and deleted it. I now have two boxes that pop up that say Cannot Send Mail - this message could not be sent because your account does not have a preferred outgoing mail server. Select from the list below(there is of course, no list below). I went back to Window > Connection Doctor and selected a preferred outgoing mail server(only one account that did not have one selected already) and still keep getting those two boxes that say Cannot Send Mail.

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Answer 5

Linc Davis

Level 10

209,547 points

Apr 23, 2015 6:01 PM in response to tacomaman

I'm not sure I understand your response. Do you have any outgoing mail servers now?

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Answer 6

tacomaman Author

Level 1

8 points

Apr 23, 2015 6:37 PM in response to Linc Davis

Probably some frustration coming out in my response. Sorry. Actually, the problem cleared itself up this morning. Two e-mails that I sent about one week ago, reappeared when I opened my Apple mail. I simply resent them and the Cannot Send E-mail boxes are gone. Everything is situation normal.

Thanks for your help!

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Answer 7

Mar 22, 2016 4:39 PM in response to Linc Davis

Connection Doctor identified three separate SMTP and IMAP connections for my address. One took a little bit of time connecting while the other two already had a green light.

I couldn't detect anything astray so closed out.

The message had been sent while I carried out that process, but I don't know if it was coincidental or cause-and-effect.

Thanks N.F. Line . (NF = Never Fails)

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