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Level 1

4 points

Mail 4.5 corrupts PDF attachments from gmail (while outlook 2011 doesnt)

I have a gmail account with scanned documents.

I add this account to in Mail and then some of the PDFs are damaged and can not be corrected. The interesting matter is that via web-access and Outlook 2011 there is not a problem.

I have tried many different solutions I could find on the web incl. here. From deleting the mailboxes to deleting the cache-files. Ultimately I deleted the whole mail app (incl. lib files with CleanMyMac), reinstalling and reinstalling the combo.

After adding the account the last time, I minimized the window, till all activity was finished and everything cashed etc.

I opened mail and again the same problem.

Additional remarks: There are many attachments with the same name, because they were send by a HP Office machine. Some have a problem most don't I would estimate the problem is in 10% of the mails.

Again via Web-access and Outlook 2011 all attachments are correct.

I could use Outlook, their calendar doesn't sync with gmail and I also don't like how outlook is handling (and messing-up) my v.cards .

Any help would be highly appreciated.

MacBookPro3,1, Mac OS X (10.6.7)

Posted on Apr 6, 2011 10:57 AM

43 replies

WilfredR Author

Level 1

4 points

Apr 7, 2011 11:46 PM in response to etresoft

etresoft wrote:
One of your e-mail messages had a good and apparently original e-mail from the HP device. I was able to send that back and forth to myself with no problems.

I'm glad you have to basics to do your analyses.

The Apple Mail setting for "All messages, omit attachments" seems a bit strange. I really couldn't get it to work.

I do not really care about this setting anymore. I just wanted to save some GBs, call it spring cleaning.

I say leave it at the default setting of "All messages and attachments" and rebuild your mailbox.

Maybe my remark about the different setting set you of in the wrong direction. I meant the before I started fiddling with that setting I also did not have a problem with apple Mail.

The reason for posting here is that since then I can not get to back to my original state (All message + attachments in Mail without damaged files).

I already did rebuild the mailbox, deleted cashed folders etc. When that all did not work, I decided to go for a complete clean start: I deleted the whole Application including hidden folders by using CleanMyMac.

I then re-installed it, run the combo update. Started the newly installed Mail and created a new account (with default setting). Left the computer alone, to prevent any glitches/interruptions till ALL Activity was finished. However still 10% attachments are damaged (looks like that the older the messages the higher the change that they get corrupted.

I tested with my own server, not gmail. I may by the only person left who doesn't use gmail. Perhaps their servers are getting overloaded.

It might be that it is due to server overload, little glitches etc. when re-downloading the whole mail box. However Outlook 2011, does not have any problem, I just create my account, it gets the messages and the are ALL ok.

The conclusion I can get to is that Mail somehow chokes when having to download a whole account even though this one is only 383MB

Any thoughts how to fix it?

etresoft

Level 8

46,488 points

Apr 8, 2011 6:26 AM in response to WilfredR

WilfredR wrote:
I already did rebuild the mailbox, deleted cashed folders etc. When that all did not work, I decided to go for a complete clean start: I deleted the whole Application including hidden folders by using CleanMyMac.

I then re-installed it, run the combo update. Started the newly installed Mail and created a new account (with default setting). Left the computer alone, to prevent any glitches/interruptions till ALL Activity was finished. However still 10% attachments are damaged (looks like that the older the messages the higher the change that they get corrupted.

Deleting the application won't help anything. If you deleted (or better, moved) the old mail folder from ~/Library/Mail, you should be able to re-download all of the messages with attachments.

Still, that may be what you have done. Those messages could be corrupt on the server itself.

It might be that it is due to server overload, little glitches etc. when re-downloading the whole mail box. However Outlook 2011, does not have any problem, I just create my account, it gets the messages and the are ALL ok.

I think I'm out of options. If I can reproduce the problem independently, I could file a bug report. If a problem is specific to your entire account, there is no way to debug that.

My only suggestion would be to delete or move your old mailbox folder in ~/Library/Mail for this account. Delete your Apple Mail preferences in ~/Library/Preferences. Run Disk Utility and Repair Permissions. Then run Apple Mail again, import your old accounts. Recreate this account and download all of the messages. I'm not entirely sure how easy it would be to import one set of accounts and create another set from fresh. You might have to recreate all of your e-mail accounts. You could always import the old accounts into old mailbox folders. It is good to do that anyway from time to time.

WilfredR Author

Level 1

4 points

Apr 10, 2011 10:44 AM in response to etresoft

All you said I've done unfortunately without success.

I have narrowed the problem down, just a little bit more. I recreated the account as a POP account and it downloaded all mail + attachment without a problem. All attachments that came in corrupted on the IMAP account, came in perfect via POP!?

Unfortunately it is not possible to first download it as POP and then change the settings of the account to IMAP.

Does this help in anyway in solving the problem?

etresoft

Level 8

46,488 points

Apr 10, 2011 5:24 PM in response to WilfredR

I would expect POP to be much more robust with attachments like this. One of the things IMAP is supposed to do is allow you to download attachments separately. In order for this to work, your messages have to be well-formed and your client and server have to be in good agreement. Neither may be true in your case. It could just be a simple network failure 10% of the time. Your connection to gmail times out while downloading a big image so the connection closes and your attachment is truncated. POP just grabs the whole message and parses it on the client side.

GSCBRL

Level 1

0 points

Apr 20, 2011 9:06 AM in response to etresoft

I am experiencing exactly the same problems as described here. I am using GMAIL and apple mail 4.5 (1084) on MAC OS X 10.6.7. My GMAIL mailbox has the size of 1.7 GBytes. I have tried to rebuild the mailbox folders many times but without success. Corrupt attachments appear mainly for old messages with large attachments.

I have installed Thunderbird on a Windows PC in order to see if the folders are downloaded propperly. With Thunderbird there are no corrupt attachments !

I am now thinking of migrating also on my Mac to Thunderbird in case there is no other solution for this problem.

Therefore I would appreciate very much if someone would find a solution for this problem.

Best regards

Jun 15, 2011 9:13 PM in response to WilfredR

+1 from me (or in actual fact a customer of mine).

Scenario is Gmail -> Apple Mail via IMAP and is not particular to my customer's laptop because I have replicated the problem on my own laptop accessing his Gmail account.

In fact it's not particular to the current version of Mail - my test laptop is running OS X 10.5.8 and Mail 3.6 whereas my customer is running 10.6.7 and 4.5.

The broken attachments are seemingly smaller (truncated?) than the originals and are unable to be opened by either Preview or Adobe Reader.

The attachments (all PDFs in this case) seem to be OK when accessed via the Gmail web interface (either viewed via Google Docs or downloaded to the laptop) and they're also OK if forwarded from Gmail to another email account.

Rebuilding the mailbox (in effect re-downloading all the messages from the IMAP server) doesn't seem to make any difference.

So this makes me think that there is some misunderstanding between Google IMAP server and Apple Mail IMAP client for some files.

etresoft

Level 8

46,488 points

Jun 16, 2011 5:54 AM in response to Kiwi Graham

Kiwi Graham wrote:

So this makes me think that there is some misunderstanding between Google IMAP server and Apple Mail IMAP client for some files.

I think you're right on the money. There have been an awful lot of strange Apple Mail problems lately that make no sense and cannot be reproduced. Gmail is always involved.

KTSM

Level 1

0 points

Jul 14, 2011 6:52 AM in response to etresoft

Is there any updates?

I have the same situation...

Thanks.

Jul 14, 2011 6:53 AM in response to etresoft

Hi,

I have the same problem with an old email attachment that can't be opened any more on both, my MBP (10.5.8), and my Mini (10.6.8). Fortunately, I still have the original file around, and diffing the hexdumps showed that the broken file simply got truncated not too far from its original end (see below).

Unfortunately, I cannot reproduce the error, but you can find the original file to play around with here:

Introduction to Random Matrix Theory from An Invitation to Modern ...

Kind regards,

Alex

[MiniMac:~/Desktop/BrokenPDF] prog% diff IntroRMT_Math54.pdf.hexdump IntroRMT_Math54_broken.pdf.hexdump

31261,31321c31261,31262

< 0007a7a0 30 20 6e 20 0a 30 30 30 30 34 39 30 33 31 32 20 |0 n .0000490312 |

< 0007a7b0 30 30 30 30 30 20 6e 20 0a 30 30 30 30 33 38 31 |00000 n .0000381|

< 0007a7c0 36 38 35 20 30 30 30 30 30 20 6e 20 0a 30 30 30 |685 00000 n .000|

< 0007a7d0 30 34 37 38 30 34 31 20 30 30 30 30 30 20 6e 20 |0478041 00000 n |

< 0007a7e0 0a 30 30 30 30 34 37 37 38 35 33 20 30 30 30 30 |.0000477853 0000|

< 0007a7f0 30 20 6e 20 0a 30 30 30 30 33 37 38 38 32 31 20 |0 n .0000378821 |

< 0007a800 30 30 30 30 30 20 6e 20 0a 30 30 30 30 33 37 39 |00000 n .0000379|

< 0007a810 38 30 38 20 30 30 30 30 30 20 6e 20 0a 30 30 30 |808 00000 n .000|

< 0007a820 30 33 38 31 36 31 36 20 30 30 30 30 30 20 6e 20 |0381616 00000 n |

< 0007a830 0a 30 30 30 30 34 39 30 34 32 30 20 30 30 30 30 |.0000490420 0000|

< 0007a840 30 20 6e 20 0a 30 30 30 30 33 38 32 34 37 30 20 |0 n .0000382470 |

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< 0007a8e0 30 20 6e 20 0a 30 30 30 30 34 38 32 34 31 37 20 |0 n .0000482417 |

< 0007a8f0 30 30 30 30 30 20 6e 20 0a 30 30 30 30 34 38 32 |00000 n .0000482|

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< 0007a920 0a 30 30 30 30 34 38 33 30 34 36 20 30 30 30 30 |.0000483046 0000|

< 0007a930 30 20 6e 20 0a 30 30 30 30 34 38 33 37 36 38 20 |0 n .0000483768 |

< 0007a940 30 30 30 30 30 20 6e 20 0a 30 30 30 30 34 38 33 |00000 n .0000483|

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< 0007a9c0 0a 30 30 30 30 34 38 35 38 34 31 20 30 30 30 30 |.0000485841 0000|

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< 0007a9e0 30 30 30 30 30 20 6e 20 0a 30 30 30 30 34 38 36 |00000 n .0000486|

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< 0007aa10 0a 30 30 30 30 34 38 37 38 31 36 20 30 30 30 30 |.0000487816 0000|

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< 0007ab10 30 20 6e 20 0a 74 72 61 69 6c 65 72 0a 3c 3c 0a |0 n .trailer.<<.|

< 0007ab20 2f 53 69 7a 65 20 35 36 34 0a 2f 52 6f 6f 74 20 |/Size 564./Root |

< 0007ab30 32 20 30 20 52 0a 2f 49 6e 66 6f 20 31 20 30 20 |2 0 R./Info 1 0 |

< 0007ab40 52 0a 3e 3e 0a 73 74 61 72 74 78 72 65 66 0a 34 |R.>>.startxref.4|

< 0007ab50 39 31 32 35 38 0a 25 25 45 4f 46 0a |91258.%%EOF.|

< 0007ab5c

---

> 0007a7a0 30 |0|

> 0007a7a1

[MiniMac:~/Desktop/BrokenPDF] prog%

Jul 14, 2011 7:21 AM in response to Alexander Klein

P.s.: Just to be sure, I viewed the message source in Mail.app, and it seems that the attachment is stored properly on the HD, but gets broken at some point during decoding:

--Apple-Mail-10--168891392

Content-Disposition: inline;

filename=IntroRMT_Math54.pdf

Content-Type: application/pdf;

name=IntroRMT_Math54.pdf;

x-unix-mode=0755

Content-Transfer-Encoding: base64

JVBERi0xLjIKNyAwIG9iago8PAovVHlwZS9FbmNvZGluZwovRGlmZmVyZW5jZXNbMS9kb3RhY2Nl

[...Some megs cut here...]

DAwMDAwIG4gCjAwMDA0OTAyMDQg

MDAwMDAgbiAKMDAwMDM3ODc1NyAwMDAwMCBuIAowMDAwMzc3MTkzIDAwMDAwIG4gCjAwMDAzNzg2

NjggMDAwMDA

--Apple-Mail-10--168891392--

Sep 5, 2011 2:08 AM in response to WilfredR

I have the same problem, my mail stored on gmail and for some pdfs i want to open in Mail.app i get an error message saying the file may be corrupted and can't be opened in preview. If i try to open the same file from the webmail it works... very annoying.

I have tried rebuilding mailboxes etc.. does not helps..

GSCBRL

Level 1

0 points

Sep 5, 2011 7:20 AM in response to WilfredR

It would be so nice if someone from Apple would finally take care about this problem which now so many people already reported.

The only solution currently seems to migrate to an other email program (e.g. Thunderbird)... very sad...

Dec 16, 2011 5:42 PM in response to WilfredR

+1 Same problem here! I'm using OS X Lion w/ Mail 5.1

About 15% of my PDF attachments are broken or corrupted...

Apple! Please!!! Do something!!!!

etresoft

Level 8

46,488 points

Dec 16, 2011 7:02 PM in response to martin129

martin129 wrote:

+1 Same problem here! I'm using OS X Lion w/ Mail 5.1

About 15% of my PDF attachments are broken or corrupted...

Apple! Please!!! Do something!!!!

There is nothing Apple can do about Google's e-mail servers.

GSCBRL

Level 1

0 points

Dec 17, 2011 2:54 AM in response to etresoft

The problem can be reproduced only with Apple`s mail application. Thunderbird, Outlook and other email clients do NOT have these problems.

I am using in parallel to Apple Mail also Thunderbird: In Thunderbird there are NO corrupted PDF attachments. So at least there is a kind of incompatibility between GMAIL and Apple Mail !

Very sad that Apple is apparently still ignoring this problem - I am very disappointed about lack Apple`s support... 😟

Mail 4.5 corrupts PDF attachments from gmail (while outlook 2011 doesnt)