Q: Messages won't send images or files

Any news on this? I still have this problem, and it is not random for me but very persistent, making Messages more or less unusable.

hi,

No new news on this.

Anecdotal evidence points to the Security Update 2015-001 that came out in January.

For some reason this seems to block the switch to the UDP port in the AIM account.

9:55 pm      Tuesday; March 24, 2015

We have two 10.8.6 OS Macs in different cities and another 10.10. Mac in the local network (Bonjour). We have AiM accounts and the local Macs can also chat via Bonjour. We cannot send pics (=jpg, png, TIFF) between any of them with any port settting (i.e. SSL and port 443 or port 5190 without SSL), meaning locally (Bonjour) and remotely (through our router and WWW) . However we can send any file if it is ZIPped and most of the time PDFs (sometimes we have to send the file twice and then it goes through once.

So this would in my opinion exclude any router port setting problem, since files go though the same port?

For screenshots which we exchange on an hourly basis we have changed the default format of OS X Grab application to "PDF" instead of PNG, so now we have something we can send. Unfortunately the PDF setting for screenshots does not apply for screenshots saved to clipboard (e.g. Command + Alt + Shift + 3) which we had always pasted directly into the chat window previously. Meaning we do regualr screenshots which appear as PDF files on Desktop and then drag those into the chat window. Maybe this helps someone

We will upgrade all macs to 10.10. soon, did anybody get this to work with all OS 10.10. and AiM Accounts?

Regards,

p.

Hi,

Just to be clear.

Early versions of iChat logged in to AIM on port 5190 using the TCP protocol.

To do certain Chats, Groups and Direct IMs, plus Sending Files including Pics-in-Chats it moved to port 5190 using the UDP Protocol.

Messages now logs in on port 443.

It still changes to port 5190 with the UDP protocol.

This Document relates to this and the Bonjour info

https://support.apple.com/en-us/HT201578

This states Bonjour needs port 5353 (It uses this even if you don't use iChat or Messages to display Bonjour "Shares"/"Servers" in the finder's Side Bar.

From the Document it lists ports 5297 and 5298 both on UDP and 5298 on the TCP Protocol as well.

As Rendezvous/Bonjour has been present since iChat 1 it would appear it follows the AIM way of switching Ports and Protocols.

Whilst I use Little Snitch that will tell you about external IPs and ports that apps are using It does not relate the Local ports so I don't have any direct info that the Bonjour Account actually does this.

Most routers will allow local traffic with the need to open the ports involved.

Between two AIM Accounts on my iMac in Yosemite I get this in the File Transfer window

I tried sending the same pic from each of the two accounts and got separate entries in the transfer window but nothing in the individual chats  (they show on the outgoing side but not on the Receiving in the other account)

The File Transfer Window indicates no issue and records them as Sent.

The Zipped item (same pic) shows and sent from one account and received on the other and the app played the sound for this  (well actually it played the Messages Received sound) which it did not for the other two attempts.

I no longer have AIM for Mac so I can't check if it is something about how it passes through the AIM servers (although it is supposed to be a Direct IM and bypass the servers).

7:54 pm      Tuesday; April 14, 2015

I finally found some relief. The steps in this link to quit Messages, then use Activity Monitor to quit/force quit (quit worked for me) imagent finally let me send Jabber picture.

http://www.mcelhearn.com/fix-a-problem-sending-screenshots-in-os-xs-messages/

Hopefully this won't be a daily thing to do, but at least it works.

Laz