Problems with Apple Mail

I have updated yesterday morning Mavericks to 10.9.4.
Since then I experience this problem: emailed photos (jpeg) arrive on the mail server (live.ca) as text.
When that happens, quitting and reopening Mail doesn't help.
Only a restart helps.
Has anyone experienced this problem?

Try downloading and applying the 10.9.4 Update Combo to see if that corrects it. If not, you may have to delete a preference file to reset things.

As an fyi, photos technically do send as text because that's what email service was originally designed to do. The email software has to convert attachments to text using MIME and the receiver converts that code back into a file. This is all supposed to happen transparently though, so you do still have something wrong going on.

BTW, try this. Select one of your messages that has an attachment, then go to the menu and select View ⇒ Message ⇒ Raw Source. You'll see some text that reads something like this:


Does the "text" you mentioned earlier look like this?

It is like this:

From: Ciro William Lucchi <[email protected]>
Content-Type: image/jpg;
x-unix-mode=0644;
name="=?iso-8859-1?Q?DSC=5F2932_iPh_=A9_2014_Claudio_D=2E_Lucchi=2Ejpg?="
Content-Transfer-Encoding: base64
X-Smtp-Server: smtp.live.com:[email protected]
Subject: 2932
Message-Id: <[email protected]>
X-Universally-Unique-Identifier: 6050AD51-2FFB-4A6F-A762-E481C97ED062
Date: Thu, 10 Jul 2014 11:04:48 -0400
To: Claudio Lucchi <[email protected]>,
Ciro William Lucchi <[email protected]>
Mime-Version: 1.0 (Mac OS X Mail 7.3 \(1878.2\))
Content-Disposition: inline;
filename*=iso-8859-1''DSC%5F2932%20iPh%20%A9%202014%20Claudio%20D.%20Lucchi.jpg
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(remainder deleted)

How do I download and apply 10.9.4 Update Combo? Thanks for the help.

You can find the Combo Updater here. Click the download link and let it finish. After that go to whatever folder your downloads are in and double click the installer.

Cavalese said:

How do I download and apply 10.9.4 Update Combo? Thanks for the help.

Click to expand...

Whoops. Forgot to add the link. Anywho, after applying as Sly indicated, if you still have a problem, you should try running Onyx's suite of maintenance and cleaning tools. You may have a buggy cache or faulty permission somewhere in your user Library. If that doesn't fix it, then I'll direct you to a preference file that will need to be scrapped.

Basically what appears to be going on is Mail is showing you the headers and source MIME code for your email, rather than "translating" it to a readable, usable form. There's no preference setting that I can find in Mail's preferences to enable that view by default, but may be one of those hidden settings embedded in the preference file itself.

Thank you lifeisabeach. What I did up to now was:
1) With Disk Utility I repaired all the Disk Permissions (there quite a lot to be repaired, but none related to Mail),
2) I ran MacKeeper to clean the computer.
This didn't help. Tonight I am going to download and apply 10.9.4 Update Combo.
I'll try again tomorrow. Meanwhile, thank you for the help.

MacKeeper? OMG... Get rid of that turd ASAP!
https://discussions.apple.com/message/24491801

Thank you very much, lifeisabeach.

I did download and install 10.9.4 Update Combo. What now happens is this:
1) On my son's account, he ran about ten tests with one or more pictures, small and large. Mail always worked.
2) On my account it doesn't work. I tried it on two different unrelated mail servers without avail.

Before continuing, I would like to mention a few facts that may help shed some light on my problems.

1) Mine is a 2009 iMac with a 2.66 GHz Intel Core 2 Duo processor and an 8 GB 1067 MHz DDR3 memory.
2) It came with Leopard installed, was updated to Snow Leopard and then Mountain Lion.
3) When Mavericks was launched I installed it from the Internet.

4) There were immediately problems. However, being non-essential, I waited.
5) Mavericks was successively updated to 10.9.1, .2, and .3 without any improvement or apparent deterioration. With 10.9.4 there came the mail problem.

6) The problems I immediately encountered with Mavericks were:
a) Significant slow-down of startup, of logout and shutdown, of account opening, of launching applications, of running applications, of running backups with TimeMachine, etc. I am talking of a factor 2 to 4 in speed, not a few percents.
b) Significant slow-down in switching applications and accounts.
c) Recently backing up with TimeMachine has become extraordinarily slow, including when switching Internet off.
d) The AddressBook (now Contacts) became almost unusable.

We are wondering, on the one hand, whether my computer is too old for Mavericks (I don't think so, however) and whether we should go back to a previous version or
whether we should reinstall the OS, but then how?

Thank you very much for your feedback.

Your iMac should be perfectly good for Mavericks. I have a 2010 and couldn't be happier. Well... now that one nagging bug that was afflicting me was finally resolved. LOL! Your sluggishness suggests a few potential problems. First off, make sure you have a backup. There is a distinct possibility your hard drive is failing, so be prepared. Once done, there are a few things to do... see my signature for instructions/downloads if needed. A couple questions though... how big is your hard drive, and how much space used/free. We generally recommend no less than 20% free space. Past that point, fragmentation becomes and increasing problem, as does reading/writing cache files. You have 8GB of RAM, so that shouldn't be a factor. You should stress test it though with Rember to be sure that isn't defective.

Test your hard drive to see if there are signs of failure. If that checks out, run Onyx's full suite of maintenance and cleaning tools. And finally, run the Apple Hardware Test if need be. Instructions are in my signature. I also cannot emphasize enough that you need to get rid of MacKeeper. There have been too many reports of that software causing problems and while it appears to have improved somewhat in recent months, there are MUCH better tools from developers with a better rep than those clowns.

The preference list you will need to kill for Mail is found here:

Make sure Mail is closed; make a backup copy of that file (copy to Desktop, for example); then delete the original. Re-open Mail and see if the problem is resolved. You may lose some other preferences you have set... they will all revert to defaults.

If that doesn't work, then you may need to delete that entire Preferences folder. As before, make a backup copy.

Dear Lifeisabeach,

My HD is a 1 TB Seagate installed on Oct 16, 2012, as a replacement for the original HD that had crashed. Capacity: 999.35 GB. Available 272.72 GB. Used: 726.63 GB. With Disk Utility, before starting the thread, I had already:
1) Verified and repaired Permissions.
2) Verified the disk: it was found to be OK.

I did some of the things you suggested:

1) I eliminated MacKeeper. The computer seems to be slightly faster.

2) I installed OnyX, but haven't run it yet, because I want to solve the mail problem first, before risking new problems. From forums, it seems that OnyX may be dangerous for unexperienced users. Though I started working on computers in 1969, my main experience is with high-level languages (Fortran, Pascal, Algol), much less with OS.

3) The path you gave me,
yourhomefolder/Library/Containers/com.apple.mail/Data/Preferences/com.apple.mail.plist
is not the one I found on my computer, which is:
yourhomefolder/Library/Containers/com.apple.mail/Data/Library/Preferences/com.apple.mail.plist
so I put to Trash this last file. Restarting Mail, that didn't solve the problem.

4) I then put to Trash the Preferences folder. When restarting Mail, the preferences had gone back to default, but the problem with the picture attachments wasn't solved.

5) I regularly ran tests, with picture attachments, on my son's account and always found that everything is fine there.

6) Another seldom-used account has the same as mine.

I am baffled. What else can I do? Do I need to reinstall Mail, i.e. reinstall the whole OS?

Thank you very much for your help.

I'm struggling to understand the problem. You said in your original post:

emailed photos (jpeg) arrive on the mail server (live.ca) as text.

Click to expand...

That's normal behavior. When the mail is then transmitted to your recipient, that receiving machine will/should translate the text back into a picture. So what's the problem? How do you know that the mail server has this text? Why does that matter? Are your recipients not seeing the pictures? If so, it's most likely on THEIR side of the system as it is the responsibility of the receiver to translate the MIME back to a picture.

To MacInWin:
Working with Apple Mail.
1) When I compose an email and attach a picture, the picture is visible as such. I then send the email and verify what is present in the Outbox (sent mail) on the outgoing mail server.
2) When I go on my outgoing mail server, the pictures are not visible as pictures, as it was before, but as text.
3) I have used two unrelated outgoing mail servers.
4) The pictures are not visible by the recipients, as pictures, but as text.
5) Recipients are on mail servers "live.com", "live.ca" and a local server. I tried several tests, including sending the e-mails back to me.
6) My son, on the same computer, using the same outgoing mail server as I do, has no problem, including sending me pictures via email.
7) This happened immediately after installing Mavericks 10.9.4 Update on Thursday 10.
Thank you for your interest.

Sorry for having bothered you so long.

Suddenly at 1 p.m. EST everything started working again.

No idea what happened. Maybe I was hacked? Maybe, by trying many changes I hit the right combination? Maybe were the outgoing mail servers simultaneously attacked? I can't understand, because I did many tests, trying to eliminate this and that factor, working several hours over the week-end.

Many thanks to all those who helped me.

Thank you, lifeisabeach. I will implement some of your suggestions.

Cavalese said:

To MacInWin:
Working with Apple Mail.
1) When I compose an email and attach a picture, the picture is visible as such. I then send the email and verify what is present in the Outbox (sent mail) on the outgoing mail server.
2) When I go on my outgoing mail server, the pictures are not visible as pictures, as it was before, but as text.

Click to expand...

That's because the picture has been converted to a MIME format for transmission. That's the way it works. What should happen is that when it gets to the receiver, it gets converted back to a picture by the same MIME process.

3) I have used two unrelated outgoing mail servers.
4) The pictures are not visible by the recipients, as pictures, but as text.

Click to expand...

Not good. That generally means that a MIME function is not working on the receiving machine. Not the sender, the receiver.

5) Recipients are on mail servers "live.com", "live.ca" and a local server. I tried several tests, including sending the e-mails back to me.

Click to expand...

You didn't say if you got them as text or pictures, or I don't remember seing that in the thread.

6) My son, on the same computer, using the same outgoing mail server as I do, has no problem, including sending me pictures via email.

Click to expand...

HIS MIME service is working as it should. Sounds like yours wasn't.

7) This happened immediately after installing Mavericks 10.9.4 Update on Thursday 10.

Click to expand...

Probably NOT related. Coincidental.

Thank you for your interest.

Click to expand...

Based on it all, it sounds like something went awry in your MIME service, leaving you unable to decode the text properly. To you it looked like NOBODY could see your pictures, but I suspect it was a just you. If, in fact, it was EVERYBODY who saw text, then your MIME service was encoding improperly. Not sure why or how it got started properly again. But you did say in your original post

Only a restart helps.

Click to expand...

which normally points to something being corrupted after launching. MacKeeper may have done something, or perhaps some other third party software you have installed could be wreaking havoc (AV, other "cleaner" and "helper" third party products, for example). Your testing, where you said

6) The problems I immediately encountered with Mavericks were:
a) Significant slow-down of startup, of logout and shutdown, of account opening, of launching applications, of running applications, of running backups with TimeMachine, etc. I am talking of a factor 2 to 4 in speed, not a few percents.
b) Significant slow-down in switching applications and accounts.
c) Recently backing up with TimeMachine has become extraordinarily slow, including when switching Internet off.
d) The AddressBook (now Contacts) became almost unusable.

Click to expand...

None of that is normal. What have you installed that claims to "help" or "clean" or "optimize" or any other buzzword, the operating system? Macs don't need anything except an occasional run of Onyx (about every six months for me). The rest of the time OSX just runs very well without any "help."

Cavalese said:

Sorry for having bothered you so long.

Suddenly at 1 p.m. EST everything started working again.

No idea what happened. Maybe I was hacked? Maybe, by trying many changes I hit the right combination? Maybe were the outgoing mail servers simultaneously attacked? I can't understand, because I did many tests, trying to eliminate this and that factor, working several hours over the week-end.

Many thanks to all those who helped me.

Thank you, lifeisabeach. I will implement some of your suggestions.

Click to expand...

Ah... good! I was just about to make some suggestions/observations, which MacInWin largely addressed already. I definitely think this was a problem with the email server, even if it was just affecting you (or perhaps a limited number of people). It definitely wasn't something wrong with the OS update, judging from the fact that your son, on the same Mac, had no issues. So there was no chance of that. It may have been related to the size of the attachments... maybe the server was choking on anything over a certain size? The server may have been accidentally clipping part of the MIME code, so it couldn't be translated back into a file. That's my best guess at the moment, but since it's resolved, no need to troubleshoot further.

One quick comment about Onyx.... it's not dangerous for inexperienced users. Far from it in fact, which is why we recommend it so often. MacInWin already touched more on that subject, so I have nothing more to add to that.

I'm a bit late here, especially considering the the problem seems to be cured, but I came across a similar thing and it just might be related, especially with the appearance of base-64 text in place of the attachment actually showing.

Bottom line fix it seems was to rebuild the mailboxes:
How to Fix Corrupted IMAP Attachments in Apple Mail - The Mac Observer

Maybe... ????

PS: What happened to Mail's "Always Send Windows-Friendly Attachments" option or have I just not found or needed it?? Now using using Mavericks 10.9.4.

pm-r said:

CLIP....

PS: What happened to Mail's "Always Send Windows-Friendly Attachments" option or have I just not found or needed it?? Now using using Mavericks 10.9.4.

Click to expand...

Mail, Edit, Attachments, check the box.