Mac iMessages immediately fail to send

I have tried everything I could find

Such as?

Hi,

As you have tried everything you will of course already deleted the .plists with the word imessages in them along with the IMAgent one and restarted Messages afterwards.

8:47 pm Wednesday; September 25, 2013

 iMac 2.5Ghz 5i 2011 (Mountain Lion 10.8.4)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad
"Limit the Logs to the Bits above Binary Images."  No, Seriously

HI,

So have you tried adding Public DNS server to the System Preference > Network Settings ?

Or making sure your router is allowing the Messages app or rather the ports it uses ?

The Mac Firewall is Allowing Messages and IMAgent if it is On ?

You have tried setting up iMessages in a Different Mac User Account ?

9:11 pm Monday; September 30, 2013

 iMac 2.5Ghz 5i 2011 (Mountain Lion 10.8.4)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad
"Limit the Logs to the Bits above Binary Images."  No, Seriously

Hi,

This is not a Beta install "roll on" issue.

The Beta worked around the layout of the various support files in OS X 10.7.x and there were changes in the position of some of these in OS X 10.8.x

Basically Messages is a completely fresh Install of the app at the Upgrade to OS X 10.8 point.

It does make use however of the com.apple.ichat.*. plists that you may have been using with iChat through a series of Upgrades.

If setting up Messages in a "test" Mac User Account works then the issue is normally with the .plists involved on you normal Mac User Account.

AS a Start open a Finder window

Then use the Go Menu > Go to Folder and then Paste the following into the Dialogue box that appears

~/Library/Preferences

In the Preferences folder find the item called com.apple.ichat.plist

Drag it to the Trash

Restart Messages.

8:28 pm Tuesday; October 1, 2013

 iMac 2.5Ghz 5i 2011 (Mountain Lion 10.8.4)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad
"Limit the Logs to the Bits above Binary Images."  No, Seriously

Hi,

So you have deleted the com.apple.imservice.imessages.plist along with com.apple.imessages.bag.plist around the first post, along with the IMAgent one (com.apple.imagent.plist)

Later you have deleted com.apple.ichat.plist

You imply the firewall on the Mac is either Off or Messages is an Allowed item.

You said you would check adding a Public DNS server to System Preferences > Network > Advanced Button > DNS tab.

And also imply you have checked the router is allowing Messages such as being set to use UPnP to allow ports to be open.

I would consider doing PRAM reset at this point.

Shut down the computer.

Restart it holding down Apple/CMD ( or ⌘)+ALT( ⌥)+P+R Keys until you have heard three Start Up Bongs.

7:43 pm Wednesday; October 2, 2013

 iMac 2.5Ghz 5i 2011 (Mountain Lion 10.8.4)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad
"Limit the Logs to the Bits above Binary Images."  No, Seriously

Hi,

I posted this:-

So have you tried adding Public DNS server to the System Preference > Network Settings ?

Or making sure your router is allowing the Messages app or rather the ports it uses ?

The Mac Firewall is Allowing Messages and IMAgent if it is On ?

You have tried setting up iMessages in a Different Mac User Account ?

I am not sure you answered on the firewall issue (I have bolded the question above)

7:35 pm Wednesday; October 9, 2013

 iMac 2.5Ghz 5i 2011 (Mountain Lion 10.8.4)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad
"Limit the Logs to the Bits above Binary Images."  No, Seriously

Hi,

I take it the iPhone and the Mac on on the same network and therefore have no real issue with sending data over the ports iMessages uses through the router ?

Did you try the Public DNS ?

Can I make sure I have this straight ?

If the Mac is Logged in the iPhone sometimes seems unable to Send Messages ?

On the 25th Sept I wrote (with some sarcasm)

As you have tried everything you will of course already deleted the .plists with the word imessages in them along with the IMAgent one and restarted Messages afterwards.

I have just noticed your reply only mentions the IMAgent .plist (whilst talking of plurals)

Yes, I have deleted the .plists with the imagent and restarted, in addition to signing out of iMessage on all my devices, restarting, and signing back in.

I am not sure you have deleted com.apple.imessages.bag.plist and com.apple.imservice.imessages.plist

I find that your replies don't always make it clear if you have done all the things that were suggested.

Hence I have also repeated the question about the DNS server settings ?

8:35 pm Monday; October 28, 2013

 iMac 2.5Ghz 5i 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

Hi,

Thanks for the clarity.

That makes it very clear what you have done.

Ignoring the "- And Now" paragraph I will concentrate for a moment on the actions and results.

Just sometimes with standard ISP DNS servers listed it seems the iMessages account cannot find the iMessages servers.

As the login is not the same port as the text data of iMessages I also suggested adding a Public DNS server.

There are several com.apple.ichat*.plists which do various things.

The ones with AIM, Jabber and Yahoo in the name hold the server and Account info for Logins to those services (So we don't need to touch them)

There are ones for Saved Status Messages (for Buddy Lists)

There is one that is effectively the Recent Items list of previous Chats/iMessages (so again we don't need to touch those)

The Subnet one refers to things for the Bonjour Account (when you have other Macs on Your LAN using iChat or Messages with Bonjour (so you can leave that as well)

That leaves com.apple.ichat.plist itself, the two with imessages in the name and the com.apple.imagent.plist.

com.apple.imagent.plist holds the Account info (the app itself (IMAgent) "Listens" to the various servers when the Mac is On but the app is not launched for Off line Messages and will start the app if one is heard)

This would be the one to delete if the app is not logging in properly.

com.apple.ichat.plist does contain the account info.

However this is more to do with the displaying of any Buddy List windows, and the Sounds set for Alert/Actions both globally and for Specific Buddies in Specific Buddy lists.

It also holds the Font and Colour choices for the Chats and Messages.

It is more about the State and display of Messages than the Login side.

If you migrated some info about an iChat version from another computer it may pay to delete this if the Font Chosen is not on this computer.

Or you could try to change the Font in Messages > Preference > Messages (Change the background colour first)

I don't think it is this as you also don't see incoming messages either and they are set separately in the Preferences > Messages.

On a side note iChat in the past would fail to launch properly if Lucida Grande was "Missing" or turned Off in the Font Book (it the Font for the Buddy Lists).

It would fail completely if Helvetica was Off or Missing.

Both are System Fonts and it would pay to check them out as well.

The two imessages .plist have the server info in one for Logging in and have the User's Apple ID and any "Aliases" such as other emails and iPhones numbers in the other.

Again deleting these can help if the login is the problem.

Safe Mode, PRAM resets and Repair Permissions can clear certain Caches and other settings that can be issues at time bit are generally low level maintenance things.

The fact the App works in Guest mode and presumably any other Mac User account does suggest it is one of the .plists involved.

At this point I would shut down Messages and delete All the .plist containing the word iChat, the IMAgent one and the two iMessages ones.

Returning to this paragraph:-

- And now, for as long as I have had iOS 7 (and I've experimented with this extensively to make sure), when I am signed into iMessage on my MacBook, no matter what network my phone may be on or whether or not my computer is on, iMessages sent from my phone almost immediately return the "message failed to send" warning just like my Mac does.

Unlike my mac, they usually will go through on the retry, or go through anyway even though it says "failed to send." But the second I disable my Mac account and sign it out, this problem completely vanishes from my phone.

This line "... But the second I disable my Mac account and sign it out, this problem completely vanishes from my phone." is about Signing Out of the iMessages account on the Mac version of Messages ?

At this point the iPhone can use either the iPhone Number or the Apple ID to Send iMessages ?

This would tend to point things back to a Login issue rather than a function issue (.plist led).

I will wait to hear the results of the mass .plist deletion and restart of the app.

8:55 pm Tuesday; October 29, 2013

 iMac 2.5Ghz 5i 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad