iMessage in Mavericks "Your message has not been sent"

Hi

Finder > Go Menu whilst hold ALT key > LIbrary > Preferences

Find and move to the Trash com.apple.ichat.plist and restart Messages

10:32 pm Friday; October 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

HI,

In the Mac version of Messages Sign Out of the iMessages account and Quit the app.

On the iPhone remove the Apple ID in Settings > Messages.

Place the iPhone in Airplane mode for 5 mins (break with server)

On coming out of Airplane Mode check Messages has the iPhone number ticked before re-adding the Apple ID.

Check both are ticked as Receive At and Send From options. (also reset your Send From choice).

Now restart Messages on the Mac.

Re-add the Apple ID

Accept the pop up(s) that tell you the iPhone is using it's number and Apple ID.

Realistically it's a Basic Reset everything.

8:02 pm Saturday; October 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

for the Points

7:01 pm Sunday; October 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

This fix worked great. Thank You :-)

You are welcome.

Thanks for letting us know.

7:56 pm Friday; April 11, 2014

I'm having the same issue - i can't send imessages from my macbook pro to iphones using imessage. the names of people i'm trying to message show up as blue (not red) and seem to try to go through, then within a few minutes i get this message:

Your message could not be sent. There was an error sending the previous message. Would you like to try to send it again?

I followed all your steps Ralph in this thread and a few others - including trashing the madrid.plist prefs and logging out of iMessage. going into airplane mode for 5 minutes. i tried to do everything in order, but where i'm getting stuck in following the above directions is when i try to remove my primary email address from imessage on my iphone - the one tied to my icloud account - i get a pop-up error saying "This email address could not be removed"

any ideas?

thanks!!

Hi,

The Apple ID on the iPhone has to be removed and not just trying to isolate it as a Send and Receive Address.

The Pic also looks a little odd.

If you read older info about the iChat App it refers to Chats (AIM, Jabber, Bonjour and Yahoo) on the type of accounts that have Buddy lists.

Whether you display Buddy List in Messages is optional.

If you read info on iMessages (which is mostly iOS device based admittedly) the documents tend to take about Conversations.

Whilst the alert is somewhat see though it only appears to have the Pink Panther pic (possibly a Top Cat character) behind it and I can't tell if it is sending an iMessage or not.

8:12 pm Thursday; July 17, 2014

yes - sorry for the confusion - i thought twice about using that screenshot - and hoped it wouldn't create more questions. the issue happens when i use iMessage to message anyone with an iphone on imessage, including all the contacts I'd previously mentioned. the background in that particular chat window was from a conversation days ago that went through just fine. the character is actually Snagglepuss (not sure if he ever made it to the UK) - my 8 year old discovered him on YouTube while on vacation with my parents and has been chatting with me on iMessage about him for the past week, hence the background image.

today when i tried to use my mac to iMessage the phones of my brother, my parents, my coworker, and my wife - all of whom use iMessage on their iphones - I got that same error. it would try for a few minutes then pop-up with that message, asking me to try again.

To your point - The Apple ID on the iPhone has to be removed and not just trying to isolate it as a Send and Receive Address.

should i try removing the ID from Settings:iTunes & App Store

or iCloud? or somewhere else on my phone? and then try to remove it from Settings:Messages?

thanks a million.

Hi,

Snagglepuss did make it here. My son (now 30 something used to watch it)

Just remove the ID from the Message app on the iPhone.

I take these particular iPhones are getting iMessages (blue sends in iOS) from other devices ?

Your Mac version can send any colour you choose but it will only appear as a "white" balloon on the iOS device when it is an incoming Message.

Outgoing messages can be blue for iMessages or Green of SMS on an iOS device.

The non delivery messages are never clear if the iPhone is out of WiFi or good enough Carrier service range or if it is Off line for some other reason or if you are not fully logged in.

8:38 pm Thursday; July 17, 2014

Thanks so much Ralph. My problem is I'm unable to remove that ID from the messages app on my phone. I get this error when I try:

Hi,

You should be able to click the Apple ID in the Messages settings and it should offer you the Sign Out option.

9:48 pm Thursday; July 17, 2014

excellent - i was able to do that. thanks again, i'll try the steps once more.

i misconstrued "remove the ID from your account" to mean actually removing the account, not signing out. and i wasn't aware of the click and hold option - that worked perfectly.

and yes, to answer your question from earlier, the phones i mentioned previously were all getting iMessages (blue sends in iOS) from other devices - just not imessage.

thanks again! I'll let you know how I make out.

so no dice. iMessage on my mac won't send anything to anyone - on iPhones or on Messages. I can use Messages to message people using AIM or Google Talk, but if I try doing it through iMessage, the send fails. any ideas?