Q: Messages fails to send first time, resending the message works….  This happens every time I send a message...

Hi,

This issue never seems to go fully away but does drop the number of people complaining about it.

Can you confirm which version of Messages you are using and which version of the OS ?

In addition to that can you tell us what you have tried ?

9:37 pm      Friday; August 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 ralph,

sure... Mac OS X 10.8.5 and previous this year.

current Messages version says 7.0.1.

only happens when sending an iMessage to another iMessage/iCloud user. does 'not' happen during a conversation except for the first time. but after any significant amount of time passes by, or if screensaver engages, or if system sleeps - then, the next/first message i send, i know i have to wait a minute for the red exclamation point icon to appear, so i can click on it to "try again". as soon as the "delivered" notice appears under it, then i know i'm good for a while. it's crazy. & frustrating. especially if you're in a hurry & need to shoot off a quick message to someone.

it's been a consistent issue, no matter who i'm communicating with. no matter if the other person is on mountain lion or lion (not sure about earlier), or iphone or ipad; always the same.

it also happens with everyone i know!!! my wife, my friends, my business associates - it's not just me.

heard a rumor today that it's not any better in Mavericks either :-(

and since we're on the topic, another issue is, if i'm chatting with someone in Messages via a different service (like Gtalk), and then either one of us tries to facetime with each other (using icloud of course), it won't connect. it will only connect if we switch services & type a message, have it deliver (after the above issue occurs), and THEN try the facetime option; then it always connects.

crazy!

HI,

Last bit first.

Messages is built on thre iChat engine.

In iChat any Account can Video Chat (except the Yahoo one in iChat 6).

There are several ways to start a chat but I used th Buddy list green Video icon for each Buddy.

To be clear this means Jabber (including GoogleTalk) and AIM Logins  can Video or Audio Only chat plus to the Screen Sharing thing for within the App.

This transfers to Messages.
By Default the Buddy lists are hidden (See Window Menu for "Buddies" - CMD + 1)

They are also joined together (See the General Section of the Preferences to Unlink them) This includes the Bonjour account as well as any AIM valid Logins and Jabber logins.

Only the iMessages account will use the Video icon to Invoke FaceTime.

(It expects that you are using the same Apple ID in both Messages for the iMessages account and FaceTime)

You are right in that you cannot just change the Contact ID from Google (or AIM) to iMessages but have to send at least one iMessages as well.

Back to the original problem.

There is this Document by Apple on the Ports FaceTime and iMessages use.

It was originally written for iPhones. (and does not mention the "iChat" type ports)

If you compare that to the Document about iChat 3 and it's ports you will see that only the range " 3478 through 3497 (UDP) " is really any different.

Now the router you have should be using UPnP to open the ports.

It is simpler in that it is effectively an ON/Off setting.

It allows Multiple computers (And/or other devices) to use the same ports.

It is needed to the Screen Sharing using AIM and Jabber accounts.

In most cases the number of ports required for Messages with AIM, Jabber, Yahoo and iMessages along with the ports needed to Audio Only or Video chat generally exceeds any table in the Port Forwarding section.

On my Modem/Router combined unit the UPnP section has  two adjustment items

The Time to Live (How Long a port is open after you last use it).

And the Number of Hops. (one Hop is router to computer)

I have changed mine to 15 mins and 2 hops.

Now and AIM and Jabber login will send text IMs on the same port as the Login.

However from the details in the FaceTime /iMessages doc it seems that the Apple ID  and iMessages logins are spread over ports 80, 433 and 5223 and the Video (FaceTime) in the bottom two groups but effectively port 16384-16402 which is the same as the iChat Video ports.

That would leave us presuming that iMessages text chats are on the  " 3478 through 3497 (UDP) " group.

My thought is that the text route, if you like, is not always open the same way an AIM or Jabber account works.

From there I am wondering if any UPnP setting is "Closing" a port if there has not been any data sent for a while.

Now I realise that this may be a case of Fuzzy Logic but I can't really see any other way you can be logged in but unable to send the first message.

8:21 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

wow, thanks for the input ralph!

tho, your "fuzzy" logic is a bit fuzzy for me ;-)

i went ahead and disabled gtalk in messages accounts. we'll see if that helps as far as when i'm communicating with someone and we wanna "facetime".

geeze, i wish there was ONE awesome app that can do it all (imessage, hangout, skype, etc).

now, about the actual issue - not sure i understand UPnP; but just in case any of this info would help 'you' understand and in case you feel up to replying again, here's some screenshots with info.

one is the UPnP page of the modem/router.

then my Messages main account window.

then some System Preferences windows.

THANKS!

Hi,

UPnP works a little like the Mac Firewall does.

That is to say that the Mac Firewall if On, then requires you to list the apps you want to allow but then any port by the app is allowed.

It is this bit about any port the app is using that is similar to UPnP.

Also control is "given" over to the app Itself or rather the data coming from the computer which tells the router which ports it needs to have open.

The Advertisement Period is referred to as the Time to Live period on some routers meaning that the router tells other nearby devices that the port is open.

Which nearby devices is controlled by the number of Hops (or how many steps) away from the router this information is past to.

Router to computer is one hop.

Router to ISP is also one hop

Router to computer via a Airport Base Station in Bridge Mode  is still one hop.

Lets say you have a router/Modem combined and then another router that cannot do Bridge mode. This would be two hops.

So is the one hop up to the ISP server and down one to the next in line end user. (it's a third step/hop to their computer).

Information about how much of the advertising data is actually seen at other end users is not clear.

Your picture seems to show the Advertising time set at 1 minute.

If this does have some relationship with how long the port is open after non use then it would appear that the port would close.

If I am right that iMessage texts are sent to the server on a different port to the Login then  even relatively small breaks in a chat are likely to result in the port closing.

On many routers the default period is 30 mins

From the "help"column on my device.

Advertisement Period

The Advertisement Period is how often the Sky Router will advertise (broadcast) its UPnP information. This value can range from 1 to 1440 minutes.  The default period is for 30 minutes. Shorter durations will ensure that control points have current device status at the expense of additional network traffic. Longer durations may compromise the freshness of the device status but can significantly reduce network traffic.

The other pics.

The TCP/IP one is similar to mine and I would not suggest any changes.

The DNS one could do with the ISP number in there as well.

Some routers show these as greyed out numbers as that get picked up from the router.

I have added my ISP's DNS servers manually.

The last pic shows an item generated by the system.

IP address that start 169.245.x.x are self-assigned (the computers issues it to itself - mostly when it can't find a network)  The *.local refers to computer names that the computer may have  (See System Preferences > Sharing - mine reads "Ralphs iMac.local" under the top text entry field.)

8:45 pm      Thursday; September 26, 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

This HAS to be a clue. I live in NYC and have never had a problem with Time Warner Cable and this issue.  I only starting having this issue when i was living at my dad's place in Florida on Comcast.  I'm now in Los Ageles on Time Warner again it not a problem.  Though I DID have a problem for a minute here and the only thing i changed was the wireless security from WPA to WPA2 (Personal).  Is it possible that WPA vs. WPA2 could be causing the problem.  I feel that would be weird but...

Hi,

It does sound a bit weird and is unlikely to have any bearing on the matter.

Unfortunately there are just too many routers out there doing so many different forms of encryption, at various stages of people updating their router's firmware that only a poll would generate the detail required to even hint at checking.

Apple do not allow Polls on these Support Community forums.

9:15 pm      Thursday; September 26, 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

WOW ralph - thanks for all the helpful info!!!

a tad over my head, but i think i grasp it generally.

here, let's see if i do or not... (LOL)... so, given all this, it would seem that we all should change which port messages/ichat uses - no?

does this all mean that the routers or ISP's are having issues with the port messages/ichat is using?

HI,

You don't need to change the ports the Messages app uses.

Most of them you can't change anyway.

Using UPnP in the router requires that for some things there is a constant stream of data to keep a port open.

As soon as that data stops the clock is running as to when the port will close.

The older "iChat Side" has the AIM, Jabber (Google included) Bonjour and in iChat 6, the Yahoo accounts.

It uses ports for login

AIM uses port 5190 on older version of iChat and port 443 in iChat 6 and Messages (Although we have been telling peopl for years to use port 443 anyway as it a port you can change)

Jabber uses port 5222 if not using SSL to login (very few servers do this) and port 5223 if using SSL.

However Google Talk will also accept logins on port 443.

Yahoo also uses port 443 to login to that server.

The AIM account will keep a constant check with the server to say you are logged in.

It will instantly update for your Buddies coming and going On-line.

The Jabber process is slightly different but almost as instant.

I have not played around with a Yahoo account to check it thoroughly but it also seems to respond to changes in the Buddy list relatively instantly.

It is less clear how the iMessages account is keeping logged in with the iMessages server.

If I send a Message to my iPhone  or even back in the other direction, I would not say it was Instant but it does seem to be about the same time delay in either direction.

As iPhones will change networks as you move about and your Mac may not always be On it is likely that the iMessages account does not keep and "Always ON" connection with the server.

You have no way to check whether someone is On Line in iMessages.

It could be as Linc said earlier that there is some form of partial outage problem with the iMessages server.

We are talking about what you could possibly change.

You have UPnP enabled and the most logical thing to change would be the advertisement time to something longer than a minute.

10:09 pm      Thursday; September 26, 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

ah. you bring up another interesting point i've not mentioned because i didn't think it was related, but...

also since my ML upgrade, i've noticed my various accounts in messages go offline'n'back periodically. drives me crazy because i have it set in prefs for a sound to occur whenver i come online or go offline, and i started noticing that sound quite often a while back. so i started keeping my messages window open and the part at the bottom left where it lists the accounts & their status; i would notice one ore all would just spontaneously go offline. they'll usually come back themselves, or sometimes, i go & rechange their status & they come back on.

i just thought it was interruptions in my ISP, but, i notice it at other places too; weird.

i'm just sick of this app. i think it's the first Apple app that i truly dislike.

so, bottom line is, there's nothing anybody can do about any of these behaviors except wait for apple to fix 'em? ugh.

thanks for all your help tho Ralph!

peace.

Hi,

To examine the behaviour more closely you can display the non iMessages accounts by using the "Buddies" option in the Window Menu.

This will display the combined list for any AIM, Jabber, Yahoo and Bonjour accounts that are Enabled and logged in.

The List can be Unlinked in the general Section of the Preferences at the Lines that says "Gather all Accounts into one List"  The default is for this to be ticked.

There is no way to see when you are logged in to an iMessages account or not (you can't tell about Contacts either).

However displaying the Buddy Lists  for AIM, Jabber and Yahoo separately should give us a clue as to what and when the internet connection is failing.

The most common cause for WiFi drop outs is other close by routers also using the same channel.

The routers come from the factory set at a Middle number  (There are normally about 15 to choose from)

Mine  actually has an Auto option and 13 channels

Some utilities like iStumbler can tell the channels nearby devices are using.

In Mountain Lion there is Apple's own version

The iStumbler one was last updated from Lion  but this will work in Mountain Lion.

My iStumbler view

I will probably change mine in the light that many nearby routers are using Channel 1

8:18 pm      Friday; September 27, 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

it can easily be the network you are on.

At my work the ports are either blocked or our ironport (web blocked) is stopping the images from going out or coming in.

Works fine if i tether to my iphone so you might need to enable upnp on your router at home.