Messages cannot send files

Hi,

I have been doing it since 2004 actually.

Re:-

Ensuring ports 443 (for Messages), 5190 (UDP for Messages), 5297, 5298 (UDP for Bonjour) and 5298 (TCP for Bonjour) are all open.

The iMessages Login uses port 443 (so does the AIM Login nowadays and Yahoo if you have the Account set up)

AIM Swaps to use port 5190 (UDP when it File Transfers).

The other three ports lists are listed as being needed by Bonjour but using Little Snitch myself I have never been able to prove it does a similar thing to the AIM account and swap port when moving from basic IM chat to ones that contain pics-in-chats.

Re:-

Making sure no-one has Little Snitch active.

Little Snitch will block (if you tell it) processes that you may not associate with Messages as such.

This is the pop up you should see if you are doing File Transfers with the iMessages Account. (note the Server and port).

Why they set up a different Process instead of the using the same one the AIM, Jabber and Bonjour ones use. It has a slightly different name.

I have tried sending pics over AIM to my MacBook Pro which is using iChat 5.0.3

I have also tried sending using Bonjour from iMac to MacBook Pro and cannot get it to work.

However the Bonjour From the MacBook Pro to the iMac strangely works.

The version of iChat says the File Transfer window is waiting fro me (in the iMac) to Respond to start sending when trying to use AIM.

However, separately the Chat window in iChat 5.x.x shows a message from the AIM servers saying the AIM Proxy has not worked and to try again and this make no changes to the File Transfer window.

2nd attempt to use Bonjour from iChat 5.x.x have also failed.

There appears to be no clear reason why it fails.

Re:-

Making sure the usernames are not overly long (there was a suggestion Bonjour has an internal limit that could result in cut off names being identical).

Bonjour items in the Finders Side Bar tend to take the name for System Preferences > Sharing

The Bonjour Buddy ID then becomes User's My Card on the remote computer@the Computer's Name

Possibly naming conventions have changed over time but I don't normally have issues (the MacBook Pro did not seem to like spaces or apostrophes when I named it where as the iMac running a much later OS version when named allows them).

However as I have had them connected it should not be the issue.

What can be an issue is naming them all Macintosh or Admin depending on the naming process you might use and whether a Diskimage is used to make them all have the same apps and settings.

UPnP came about as iChat 3 and 4 used so many ports you could not open them all in Port Forwarding set ups.

Video and Audio Only chats used 22 ports

AIM had three

Bonjour claimed to use 3 in the Apple Documentation

Jabber claimed to need at least one but was in fact 2 to cover non SSL Logins.

See Using iChat with a firewall or NAT router - Apple Support

Two things you don't mention that you have tried.

NVRAM (PRAM) resets How to Reset NVRAM on your Mac - Apple Support

and a Safe Boot

Repairing Permissions has not appeared in Disk Utility in El Capitan and was always decried as useful in many quarters although others swore by it.

Lastly you might want to look and Read and Write permissions.

This has become much more complicated with some apps like Messages being able to be Sandboxed which adds several layers of Read and Write folders that you also need to have access to be able to Write even to the .plists

I would take a look at this Thread and the Helpful (Orange) marked test post and the Solved Green one if required.

The Original post is followed by the Solved one but the Helpful one you should start with appears next.

9:42 pm Thursday; July 21, 2016

Hi,

Sorry for the delay I was away for the week end watching motorbikes.

Have repaired permissions on the older OS machines, did not help.

On older machines that have Disk Utility with the Repair Option you are only checking and repairing the System Side stuff. It does not touch the User's folders at all.

The Helpful and Solved posts from this thread Try safe mode if your Mac doesn't finish starting up - Apple Support are the way to go.

Linc Davis replied with a test Terminal Instruction in the orange Helpful post.

Later he post the Green Solved correction Instruction. (but it is joined to the Original Post so you see it first)

Whenever you test you will get some file showing and having lost either Ownership or Permissions.

However you may have lots more then Linc's suggested 41 if you have never run such an instruction.

I just noticed I have already linked to that thread.

Ok,
Paths.

The ~/ is quite important as it denote the User's folder.

~/Library/Messages Attachments is the "History" of what has transferred already.

It could be you have lost Permission to Write to it.

However it gets written to via ~/Library/Containers/com.apple.iChat/Data/Library/Messages and then an Alias pointing to the Attachments folder.

Again you have to have permissions and Ownership of all the containing folders. (Hence in this case the Terminal test is realistically faster although it can take some time)

I would not delete the end Attachments folder (you have to remake the Alias as well and drag it to the other location)

I also would not delete ~/Library/Containers/com.apple.iChat/Data/Library/Messages/Archive (or in some cases that is an Alias to ~/Library/Messages/Archive which I think you might have).

~/Library/Caches/com.apple.iChat holds stuff for Jabber (up to you if you delete or not)

~/Library/Caches/com.apple.Messages holds the Pictures folder (all the Buddy pics that are incoming from the AIM and Jabber servers you use). (Again up to you the server you login to will send them again).

Also see these:-

You can see the Path Bar across the bottom for the Location.

The highlighted ones have one called FileTransferController.

It is unreadable in Quick Look and also in Xcode

Deleting it will remove all items from the history of the File Transfer window (Window Menu > File Transfer)

Other than the fact it does hold all the info on File (and pic) transfers it is not clear exactly how much of the History is held here or whether it will re-survey the Attachments folder (I don't think it will do this last but I have not tried it)

As you can see the items that now link to the Messages app and many and wide spread and tracing down an issue like this can become endless.

I would try the resetting of the Ownership and Permission first. (from the other thread)

9:51 pm Monday; July 25, 2016

Hi,

I understand your frustration as I often find now Messages does not do things that were clear in iChat and often not in the same way.

The additional Read and Write routes through ~/Library/Containers/com.apple.iChat/Data/Library and the addition on SOAgent into the Containers route as well.

The Server version is not really my thing and there used to be a Poster I would recommend to people to read and Post to (Tim Harris) but it appears he has not posted for a long time.

From what I do remember for many of his posts was sorting out reverse DNS settings to do with the server name.

I sometimes feel Apple have iOS-ed Messages to death.

for the Points

9:28 pm Thursday; July 28, 2016