IMac Mail strips sender from sent mail

I'm helping a friend who has an unusual problem with Mail on their iMac (10.9.5).
This first part may be a red herring. There are four email accounts on the machine iCloud, Gmail, Yahoo, and one other linked to a domain name. For no apparent reason all four accounts suddenly stop working. If you take all accounts off-line and then back online again, sometimes three or four times, they will start working again. Similarly, if you restart the machine two or three times they will often start working again but stop after a couple of days. Both of these methods make no changes to any of the settings.
However, that is not the problem I'm looking for an answer to. The iCloud, Gmail and Yahoo accounts all work exactly as expected. The fourth account sends email OK but when it arrives it says "no sender". A machine running Windows, an iPad and an iPhone all have that account on them and are all using the same outgoing server settings but they can all send email without stripping the sender's details. The sender details do appear on the email in the Sent box of the iMac but not on the receiving machine. However, if the receiver looks at the full headers of the email, the Reply To Address is there.
I can only think of applying the 10.9.5 Combo Update or updating to 10.10. Any other suggestions?

Update released by Apple today can help you remove attachments from sent mails.
Open the sent mail: click on "MESSAGE", then go to REMOVE ATTACHMENTS.
And that's all.

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HT2500 without changing settings, iMac mail V4.6, 1)will not save password 2)takes accounts offline 3)will not except password 4)will not send mail from accounts every time.     What happen?

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Hi Nuch1,
I found an article that is contains very thorough Mail troubleshooting steps:
OS X Mail: Troubleshooting sending and receiving email messages
http://support.apple.com/kb/TS3276
You can use that article to figure out what part of the email "ecosystem" is the cause of the issue, and it can also help you attempt to resolve it.
Hope that helps,
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Is it possible to get my email folders from my iMac mail tool up to my icloud account?

Is it possible to get my email folders from my iMac mail tool up to my icloud account?
I would like to access my mail tool folders while I am traveling overseas with my ipad.
Alternately, is it possible to get my mail tool folders onto my ipad?
imac: Mac OS X Version 10.7.5
mail tool: Version 5.3

Your iCloud cannot access other accounts. You can set up the Mail app on your iPad to access other accounts just the same as on your Mac - the only issue might be with the ISP who provides your internet connection, as some services require you to be actually connected to them to send, and possibly even to receive though that would be more unusal.
If any of your other accounts provide webmail you could use that.
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Try rebuilding the mailbox. This can take awhile if you have a lot of mail.
Rebuild mailbox
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2. CC/BCC yourself and then create a mailbox under On My Mac where you can drag sent e-mails to for storage.
Send Apple feedback. They won't answer, but at least will know there is a problem. If enough people send feedback, it may get the problem solved sooner.
Mail Feedback
Or you can use your Apple ID to register with this site and go the Apple BugReporter. Supposedly you will get an answer if you submit feedback.
Feedback via Apple Developer

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Hi!
How do I add an e-mail adress to send from in Mail? I do not want to add a new acount, just an e-mail adress that is shown to the reciver that the e-mail was sent from a specific adress. You can choose in the menu of a new e-mail which adress you want to send from - and I had that earlier. But now suddenly my icloud-adress appears as an option instead of the e-mail adress I want to use. So how can I add a new one?
Best regards,
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Please don't post the same question multiple times! Instead answer the questions in your original topic.

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Confirm you did this: https://support.google.com/mail/answer/1173270?hl=en
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I've been using Mail app with AOL accounts and the current settings for years with no trouble. This is new.
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i.3d wrote:
I assume you are talking about the Apple's Mail
Yes, this is the "Mail and Address Book" forum after all!
i.3d wrote:
Start Mail, go to Preferences / Accounts.
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Tick: Use only this server.
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Hi all,
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Regards,
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Hi
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For more details:
/people/prasad.ulagappan2/blog/2005/06/07/mail-adapter-scenarios-150-sap-exchange-infrastructure
Regards
Monika

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I use Gmail as my main personal email account and usually use with Mail via POP.
I also have Gmail set up to send from another account (my work address) which I can do by selecting a different "From".
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Is it possible to get the same results directly within Mail? (Not a huge problem if not, I can just log onto the Gmail website, but it would be nice to use Mail if possible).

http://forums.macrumors.com/archive/index.php/t-573678.html
I've had the same issue as you, and found this helpful.
Basically go into the Mail preferences and under accounts add the accounts (which Gmail gathers) that you want to send from to the "Email Adress" bar using a comma. For example:
Email Adress: [email protected], [email protected], [email protected]
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It can't seem to automatically respond to emails using the address it was sent to unfortunately, which Gmail cleverly does. But it's a step closer.
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Please very carefully read and use Apple's Can receive email, but not send email advice letter.

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IMac Mail strips sender from sent mail

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