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Mail.app corrupting attachments

16253 Views 54 Replies Latest reply: Mar 10, 2014 1:37 PM by wnaed RSS
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Simon Gray Calculating status...
Currently Being Moderated
Apr 22, 2012 8:20 AM

I upgraded to Lion just last week as I bought a new iMac and I now discover that after 5 years of Mail.app behaving perfectly on all the previous versions of OSX, in Lion it now either corrupts JPG and PDF attachments, fails to attach them at all, fails to save the attachment with the email in the 'Sent' folder and fails to display inbound attachments that display perfectly in any other mail client.

 

I have browsed all the discussion threads in this forum and have yet to find any anwers.

I've tried rebuilding all mailboxes, deleting and recreating all email accounts, switching 'keep copies of all emails attachments' on AND off

and nothing seems to fix the problem

 

This really is quite serious and I am going to be raising this issue with Apple Technical Support first thing Monday morning.

I would appreciate any insights anyone may have as to workarounds to this problem.

 

regards

Si

  • etresoft Level 7 Level 7 (23,905 points)
    Currently Being Moderated
    Apr 22, 2012 8:37 AM (in response to Simon Gray)

    Simon Gray wrote:

     

    I have browsed all the discussion threads in this forum and have yet to find any anwers.

    Because no one else has experienced this. Perhaps your e-mail server changed at about the same time you upgrade to Lion.

     

    If you want, you can send a test message to me at info at etresoft dot com and I can tell you if it is really corrupted and maybe how it happened.

  • etresoft Level 7 Level 7 (23,905 points)
    Currently Being Moderated
    Apr 22, 2012 2:30 PM (in response to Simon Gray)

    Simon Gray wrote:

     

    Unfortunately this is not the case: I have the same email accounts for over 6 years and have never, ever had a problem with Mail.app until I started using Lion.

    I can confirm this behaviour began with Lion and occurs with both IMAP and POP3 email servers.

     

    You are absolutely positive your ISP has made no server changes? You have tested Lion with other ISPs and found the same behaviour?

     

    I can confirm that if the attachment is added as the only content (i.e. there is absolutely no text in the body of the email) then everything works but if you so much as a single whitespace to the body of the email, then the attachment gets corrupted.

     

    This just sounds like a classic e-mail filtering problem. Your ISP takes your message, breaks it apart, scans it for malware, the reassembles it and sends it on its way. The problem is that any ISP silly enough to try that is also silly enough to buy expensive software that does it poorly.

     

    My thanks for offering to examine the email but I raised a bug report with Apple already and am awaiting feedback.

    Keep waiting for that feedback!

  • etresoft Level 7 Level 7 (23,905 points)
    Currently Being Moderated
    Apr 22, 2012 5:43 PM (in response to Simon Gray)

    Simon Gray wrote:

     

    I am Principal Software and Systems engineer

     

     

    Me too

     

    I have two ISP's and three email accounts, all completely independent and I have tested Lion Mail.app on all the combinations. I have also tested Snow Leopard Mail.app against all the same combinations and there are no problems with attachments whatsoever under that earlier version of OSX.

     

    I have been able to further refine the precise nature of the problem with the attachments: it occurs only with image files (jpg, png, bmp, gif), it does not occur with PDF, doc, rtf, xls, zip or tar files.

    When I have little more time during the week, I will dump the raw source of the mail files and debug exactly where Lion's Mail.app is going wrong.

    Complete and utter nonsense. Don't you find it strange that the millions of other Lion users haven't noticed anything?

  • brettrp Calculating status...
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    Apr 23, 2012 11:59 PM (in response to etresoft)

    It's not 'complete and utter nonsense'.  I have the same issue.

     

    My mail is hosted on Gmail (Google apps for domains).  Attachments for old emails are corrupted in Mail.app.  If I locate the same attachment using the Gmail web client, the attachment is fine. (That I can still get my older attachments via Gmail is the only reason this isn't a total disaster.)

     

    I also have multiple email accounts hosted in different places, and I also have seen corrupted attachments across different accounts.

     

    Newer emails (for some value of 'newer'; I'm not 100% sure when this started happening) are fine.

     

    I've tried trashing all my attachments and asking Mail.app to rebuild the mailbox, to no avail. 

     

    Googling "mail.app corrupt attachments" suggests that it's not an isolated problem, even if it's not common.

  • etresoft Level 7 Level 7 (23,905 points)
    Currently Being Moderated
    Apr 24, 2012 4:52 AM (in response to brettrp)

    That is just a gmail problem. Take it up with Google.

     

    The original poster didn't mention gmail and implied that the problem occurred across different email servers, although me may not have known the difference between an ISP, server, and account.

     

    Gmail is one of the few servers I have never tried, but I have no intention of allowing Google to read my email.

  • kabbott Calculating status...
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    Apr 24, 2012 4:58 AM (in response to brettrp)

    I am having a similar problem: I just received an email with no body, just a jpg attachment. The mail app in Lion displays the attachment in its raw text encoding, rather than decoding the jpg file and displaying it inline. Here's what the message looks like on receipt:

     

     

    --Apple-Mail-3-435435404

    Content-Disposition: inline;

              filename=finger_monkeys_11.jpg

    Content-Type: image/jpg;

              x-unix-mode=0644;

              name="finger_monkeys_11.jpg"

    Content-Transfer-Encoding: base64

     

    /9j/4AAQSkZJRgABAQEASABIAAD/2wBDAAYEBQYFBAYGBQYHBwYIChAKCgkJChQODwwQFxQYGBcU

    FhYaHSUfGhsjHBYWICwgIyYnKSopGR8tMC0oMCUoKSj/2wBDAQcHBwoIChMKChMoGhYaKCgoKCgo

    KCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCj/wAARCAJEAZADASIA

     

     

    I too am using gmail, but just a personal gmail account.

    This is the first time I've seen this, but I have only had this iMac a short time.

    The same attachment displays correctly as an image when viewed on the web client for gmail, or via the gmail app on my Android phone.

     

    So count me as one other person having a similar problem. Perhaps it isn't "complete and utter nonsense", just a rare combination of circumstances that affects only a few people.

     

    Ken Abbott

  • brettrp Level 1 Level 1 (0 points)
    Currently Being Moderated
    Apr 24, 2012 6:04 AM (in response to etresoft)

    Great to see that you're such an expert in a problem that you've never seen with a mail server you've never used.

  • etresoft Level 7 Level 7 (23,905 points)
    Currently Being Moderated
    Apr 24, 2012 10:44 AM (in response to brettrp)

    brettrp wrote:

     

    Great to see that you're such an expert in a problem that you've never seen with a mail server you've never used.

    Precisely!

  • etresoft Level 7 Level 7 (23,905 points)
    Currently Being Moderated
    Apr 24, 2012 10:53 AM (in response to kabbott)

    kabbott wrote:

     

    I am having a similar problem: I just received an email with no body, just a jpg attachment. The mail app in Lion displays the attachment in its raw text encoding, rather than decoding the jpg file and displaying it inline. Here's what the message looks like on receipt:

     

     

    --Apple-Mail-3-435435404

    Content-Disposition: inline;

              filename=finger_monkeys_11.jpg

    Content-Type: image/jpg;

              x-unix-mode=0644;

              name="finger_monkeys_11.jpg"

    Content-Transfer-Encoding: base64

     

    /9j/4AAQSkZJRgABAQEASABIAAD/2wBDAAYEBQYFBAYGBQYHBwYIChAKCgkJChQODwwQFxQYGBcU

    FhYaHSUfGhsjHBYWICwgIyYnKSopGR8tMC0oMCUoKSj/2wBDAQcHBwoIChMKChMoGhYaKCgoKCgo

    KCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCj/wAARCAJEAZADASIA

     

    I know there is more to it than that.

     

    Perhaps it isn't "complete and utter nonsense", just a rare combination of circumstances that affects only a few people.

     

    The idea that Lion is unable to send uncorrupted images attachments via any e-mail server is what is complete and utter nonsense. The idea that Lion is unable to send uncorrupted images attachments through undocumented, custom servers that do not comply with MIME standards is quite likely.

  • 3141 Level 1 Level 1 (0 points)
    Currently Being Moderated
    Apr 24, 2012 12:18 PM (in response to Simon Gray)

    I am having the same problem. No change in mail provider or ISP. Thunderbird mail client does not corrupt PDF attachments. see below:

     

    --Apple-Mail=_4AD03BC2-0708-468A-8BB9-830FA9065EEE

    Content-Disposition: inline;

        filename="inv 762.pdf"

    Content-Type: application/pdf;

        name="inv 762.pdf"

    Content-Transfer-Encoding: base64

     

    JVBERi0xLjMKJcTl8uXrp/Og0MTGCjQgMCBvYmoKPDwgL0xlbmd0aCA1IDAgUiAvRmlsdGVyIC9G

    bGF0ZURlY29kZSA+PgpzdHJlYW0KeAGVWttyG8kNfZ+v6Ic8DKtMae4z3KfEcuJyqrzxhZVNVTYP

    XC4VM6ZEi6SV6BPzE/stew4aPT2XHkpcV+1ophto4DSABtB8MB/Ng0nwr0ozUy8yc9iYn8y9ub45

  • mrfixit8311 Calculating status...
    Currently Being Moderated
    May 7, 2012 2:54 PM (in response to Simon Gray)

    We are experiencing the same issue after upgrading from Snow Leopard Server to Lion Server.  GMails not part of our equation at all.  Its random, with no logical pattern to disseminate between why one document or image comes through fine and the next comes through encoded. 

  • reggieh Calculating status...
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    May 8, 2012 9:23 AM (in response to Simon Gray)

    I recently did the lion upgrade and I'm having the same issue with emails. I'm finding it has something to do with signatures. When sending an email with a signature, attachments (such as PDF) sometime show or don't show up at all to the receiver. When i don't send emails with a signature, all seems to send fine and the receiver is able to see attachments properly.

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