Message Pic Transfer Failure

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Level 4

1,397 points

Message Pic Transfer Failure

Over the last two days, the Messages Application on both my iMac and MacBook Pro is experiencing a problem.

Specifically, when a jpeg file is sent from an iPhone, it is not received by either my iMac or MacBook Pro. I can send jpegs from my computers via Message, but after one is sent, the ability of the Messages App to receive subsequent texts or iMessages is reduced (seems like something is "clogging the pipeline..."). Simple text messages appear to be received without any problem, that I am noticing...

When I check Messages file transfers on either computer, (Window>File Transfers), I can see that any jpegs recently sent from an iPhone, are either in a hung process of downloading, or if they have been sitting long enough, there is a message that the "Vendor request failed." A couple of other jpeg file transfer failure messages read, "The server returned HTTP status code: 401."

I have signed out of, and re-signed back into iCloud on both computers, but this has not solved the problem. I though it was an interesting coincidence that both computers experienced the same problem at the same time, and am wondering if there is some type of external network problem...

Thanks for any thoughts...

Bob

iMac, OS X Yosemite (10.10.5), Mac Plus, MacBook Pro

Posted on Jul 16, 2016 12:12 PM

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Answer 1

Bob Gold Author

Level 4

1,397 points

Jul 16, 2016 12:35 PM in response to Bob Gold

I am also seeing a new message under file transfers, "NSURL Session error: The operations couldn't be compleded. (NSURLErrorDomain error - 1003.) ((null))

I got the above message after resetting my router...

Bob

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Answer 2

Jul 17, 2016 11:48 AM in response to Bob Gold

Hi,

What were the changes achieved by resetting the router ?

7:48 pm Sunday; July 17, 2016

 iMac 2.5Ghz i5 2011 (El Capitan)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 iPhone and an iPad (2)

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Answer 3

Bob Gold Author

Level 4

1,397 points

Jul 17, 2016 2:40 PM in response to Ralph-Johns-UK

No real changes that I can discern. Still unable to receive jpeg files on my laptop and iMac.

I've been doing a bit of experimenting, and have been able to send and receive pdf files... I'm going to convert a jpeg to a pdf and see if it can be sent and/or received... Don't know if the issue has to do with the type of file, or perhaps its size...

Bob

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Answer 4

Jul 18, 2016 11:58 AM in response to Bob Gold

Hi,

I meant what were the changes to the router ?

Routers allow ports to be open by different methods which are mostly defined by what you want the computer to do behind the router.

What method was the router using before ?

What is it using now ?

If it is now listing apps and the ports they use by name which ports have you got open for Messages ?

It sounds if not much was changed on the Router.

Whilst not a fix - either placing the pic in a folder or Zipping it first tends to see it delivered even if it cannot be In line.

7:58 pm Monday; July 18, 2016

 iMac 2.5Ghz i5 2011 (El Capitan)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 iPhone and an iPad (2)

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Answer 5

Bob Gold Author

Level 4

1,397 points

Jul 19, 2016 10:41 AM in response to Ralph-Johns-UK

Other than forcing the router to reset, I have made no changes to it... I don't know how to change the various ports, nor do I know what ports Messages is using.

Messages on my laptop was working normally while I was on a trip, and using different networks...pics were transferred to and from the laptop, via Messages, normally.

It was after I returned home, that I noticed both of my Macs were having the above-mentioned problem with picture transfers, prompting me to suspect that something on my DSL modem, and/or Time Capsule Airport router had changed.

I'm not sure where to go from here...thanks for any thoughts...

Bob

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Answer 6

Bob Gold Author

Level 4

1,397 points

Jul 19, 2016 11:00 AM in response to Bob Gold

According to If you use FaceTime and iMessage behind a firewall - Apple Support, the ports that Messages uses are 80, 443, and 5223. A check of those ports indicates that they are "stealth" (https://www.grc.com/x/ne.dll?rh1dkyd2)

Text traffic is successfully transferred to/from Messages... Pics are not. Tried to receive a large pdf file, and it failed to come over to the Mac...

Bob

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Answer 7

Bob Gold Author

Level 4

1,397 points

Jul 19, 2016 11:58 PM in response to Bob Gold

And another thing... It seems that, since this problem started, when someone attempts to send me (for instance) a jpeg, messages is treating the incoming jpeg as a "file transfer." That is to say, anything actually received, is downloaded into my downloads folder... I don't believe that is the behavior of incoming jpegs I've seen in the past... I'm assuming that any message attachments are stored in a messages (or ichat) folder, somewhere in the bowels of OS X...

Additionally, a file that fails to display in Messages, appears to be renamed (as viewed in the file transfer window). For example, a file, IMG_7130.mov, attached to a message and sent, appears in the file transfer window as IMG_7130.MOV.mov (and it's a hung transfer, that times out coming to my computer).

Bob

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Answer 8

Jul 20, 2016 1:35 PM in response to Bob Gold

Hi,

Pics-in-line have always been File Transfers since iChat 1

Sometimes that come as Files and can be seen in the File Transfer window (See Window Menu)

I had not noticed any file renaming when I have had this issue.

As I said Zipping (Click on hold and Pic and choose Compress) a pic first or sticking in a folder (which is then automatically zipped) get around the issue of not being delivered.

Technically Messages uses these ports as the AIM and Jabber accounts can also do Video Using iChat with a firewall or NAT router - Apple Support

iMessages itself does use just the three ports.

Port 443 is a secure (SSL) login to the server.

The 5223 is also using SSL but is the feedback whether a person is on iMessages

The Port 80 is used to check on your Apple ID.

IF you were using AIM then that would login on port 443 and then File transfers move port to 5190 using the Internet Protocol UDP (Same sort of things as HTTPS and FTP - just the manner of the internet connection).

You only seem to be talking about iPhone and Macs using iMessages.

Messages is made up of many different Processes.

These two are the ones for logging in iMessages

There is a separate one for iMessages File Sends (As opposed to AIM or Jabber) that can be blocked by apps like the one shown.

This is called Little Snitch and is a firewall with tweaks that show you every connection all apps try to make, either incoming or outgoing.

You have pops ups like this:-

Any chance you have an app like this ?

9:31 pm Wednesday; July 20, 2016

 iMac 2.5Ghz i5 2011 (El Capitan)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 iPhone and an iPad (2)

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Answer 9

Bob Gold Author

Level 4

1,397 points

Jul 21, 2016 9:13 AM in response to Ralph-Johns-UK

No...I don't have an application like Little Snitch...

I discovered something rather interesting this morning... A relative sent some jpegs via his iPhone, and they were received on my iPhone (as expected), as well as my iMac and MacBook (which surprised me a bit, given their recent history not to receive jpeg files...)

I checked the downloads folder on my MacBook Pro, and the jpeg files were not there. I then opened Messages File-Transfer window, and saw those jpeg files listed. Clicking the magnifying glass symbol to the right of each file, then caused the respective jpeg file to be moved to my computer's download folder.

So, my impression of what the file transfer window does apparently has been incorrect... It doesn't show where files have been stored...rather it takes those received files, and places them in the download folder. I don't know if they are copied or moved.

Also, it appears that my problem may be more of a synchronization problem between my home computers and iPhone, since it appears that files sent from a third-party via iMessage can be received by my iPhone and computers, while similar files sent from my iPhone, via iMessage, will not show up on my computers (as used to be the case until recently)...

More sleuthing to do, I suppose...

Bob

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Answer 10

Jul 22, 2016 11:49 AM in response to Bob Gold

Hi,

The File Transfer window will "point" to the location of the pics and file Sent by you.

If it downloaded the files/pics then it should also point to them in the downloads folder.

It should possibly show you the ~/Library/Messages/Attachments folder if it is showing the pics in-line in the chat.

The issue is looking like the File Transfer is stopping where the old Accept/Deny pop up window for the first item from that Buddy or Contact used to be.

The trouble with iOS-ing everything is that you lose detail in some areas.

Now that might be a Read and Write issue to do with the Attachments Folder.

You would need to access the folder and do a Get Info (Right click and select Get Info) and check the info Panel at the bottom.

you have to unlock the padlock and check the cogwheel type icon after selecting your Name (me) account.

10:08 pm Thursday; July 21, 2016

 iMac 2.5Ghz i5 2011 (El Capitan)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 iPhone and an iPad (2)

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Answer 11

Bob Gold Author

Level 4

1,397 points

Jul 22, 2016 11:49 AM in response to Ralph-Johns-UK

Ralph,

Thanks for your input...

Interestingly, my MacBook Pro looks like it has begun to sync it's messages with the messages received on my iPhone. Pictures are showing up as they ought to, on the MacBook... I'm not sure I changed anything on this system over the past 24 hours...

My iMac is still not syncing properly... I took a look at the ~/Library/Messages/Attachments folder on both machines, and as of the last week, pics aren't showing up (being saved?) to this folder on the iMac...

I checked the permissions on the above folder (on the iMac), and they appear to be correct. I repaired permissions, on the iMac, but this odd behavior (no pic received) has not changed. In fact, right now, the Message app on the iMac appears to be hung... Nothing received at all (text or pics), for the last 12-or-so hours...

Update: I just sent a jpeg and text from my MacBook Pro to my iPhone, and my iMac just synced it properly... Texts for the last 12 hours, are not syncing...somewhere in limbo, I guess... I'll keep monitoring the iMac.

"Curiouser and curiouser...."

Bob

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Answer 12

Jul 25, 2016 1:06 PM in response to Bob Gold

Hi,

The Disk Utility > Repair Permissions does everything but the Users folder so it will not have changed anything.

Also although Files and Pic are store in ~/Library/Messages/Attachments and then a folder linked to that specific chat, the Read and Write route is more complicated.

It is placed there via ~/Library/Containers/com.apple.iChat/Data/Library/Messages and an Alias called Attachments that points to the location ~/Library/Messages

Use this Thread Try safe mode if your Mac doesn't finish starting up - Apple Support

Start with the orange Helpful marked on by Linc Davis

If you have some files or folders that have "lost" Ownership or Permissions use the green/Solved marks post to correct them.

9:06 pm Monday; July 25, 2016

 iMac 2.5Ghz i5 2011 (El Capitan)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 iPhone and an iPad (2)

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