Can't make direct connection w/ iChat no matter what... HELP?

Discussion in 'Mac Basics and Help' started by agentphish, Mar 2, 2008.

  1. agentphish macrumors 65816


    Sep 7, 2004
    "Communications with the AIM proxy timed out. Try Again."
    Is the error that my friend and I get when I try to send him a pic or a file via iChat.

    He is the ONLY user i've ever had this happen with.

    He has a macbook, I have a powerbook.
    He has a Linksys WRT54G, I have a WRT54GS
    We are both on 10.5.2
    We are both DMZ in our routers.
    We are both using LittleSnitch on our systems, but any connection is allowed forever in iChat in the LittleSnitch setup.
    We both have the apple firewall disabled.

    The strange thing is that I can use ARD and connect to and observe or control his computer, but i can't even send a file via ARD's drag and drop file xfer feature.

    I don't get this at all. He claims that when he first got his MacBook he was able to send and receive pics and files with others on his buddy list, but now he can't. He has never been able to w/ me from day one.

    Does anyone have any suggestions on what I could try?
  2. seabass1213 macrumors newbie

    Mar 1, 2008
    I think I might know what to do. Sometimes ichat has a little thing where it wont allow you to send the "original" copy of a file. Sometimes it does it, sometimes it doesn't. It happens to me also. From here, go to finder, find the file you would like to send to the person, the control click, and click duplicate. Now try sending it to your friend, and see what happens. I hope this helps you in the future if it works. If it doesn't reply back. Thanks.
  3. agentphish thread starter macrumors 65816


    Sep 7, 2004
    It seems as though changing the connection port for the AIM server from the standard 5190, over to 443 seemed to solve the issue. It's honestly the ONE thing I didn't even think of trying.

    Quite strange if you ask me because i've never really had any issue w/ 5190 since way back in the day, like 1998.

  4. phiberglass macrumors 6502a


    Oct 3, 2007
    You may try adjusting the ports or opening the ports on your router. I find that I cannot connect to a lot of people, but other people I always can so I know the problem is not on my side.
  5. cooker47 macrumors newbie

    Mar 2, 2008
    iChat V4 firewall and ports

    I had a caller today who was trying to get iChat V4 working on OSX 10.5.1 through his ISP's router, which has custom firmware and built-in NAT firewall.

    I Googled for "iChat port forwarding" and found 2 Apple documents from 7/2007:

    The second one suggested forwarding ports 5060, 5190, 5220, 5222, 5223, 5297, 5298, 5353, 5678, 16384-16403 and we quickly set this up for both TCP and UDP just to try it. It did not work and neither did putting his computer in the router's DMZ. His OSX 10.5.1 firewall was set to "allow all".

    I was a bit concerned that he was only at 10.5.1 and might need 10.5.2 for some firewall change or maybe some iChat V4 update if there is one. He is going to try that and let us know if it works.

    The worst case may be that this just won't work through his particular router, which might explain why it works for some partners and not for others as mentioned in an earlier post. There seem to be various lists out there of what applications do or do not work with various routers and firmware.

    I'll update this post if find out more.

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