Any tips to solve iMessage issues on 10.15.5?

[Donnation]

I have constantly had issues with iMessage on Catalina and honestly I'm pretty much done with using it at this point. Messages don't come through sometimes, contacts don't fully sync, and its just overall very buggy. Does anyone have any tips on how to improve it or am I just stick with it like this with Catalina. I have a different device running Mojave and it never has a single issue. Really frustrating.

 

[0128672]

More details would be helpful. For the messages that don't arrive, are they iMessages or SMS? When you say "contacts don't fully sync," can you explain more about this? What are your Messages settings on this Mac, and what Mac is it?

 

[Honza1]

Your experience is unusual - and poorly described. It is therefore something specific on your system, which can be fixed.
I had similar issues on prior macOS/iOS systems and typically were solved by logging out of iCloud and logging in back. Somehow, the certificates used by the system to authorize connections became invalid for some tools. This can be provoked by system upgrade when more than usual number of things change, but does not need to be.
Try logging out of iCloud - you may need to logout both in system Preferences (which credentials are used for Contacts, which is what Messages are using) as well as Messages and likely FaceTime. You may want to uncheck and recheck various options you have selected there to refresh settings, in case they go corrupted. If it still cannot be sorted out, it may be configuration (plist with configuration) for Messages is corrupted or Keychain is corrupted. There is instructions on like (google it) how to reset those.
In any case, it should be working. Most people have no problems.

 

[Donnation]

Your experience is unusual - and poorly described. It is therefore something specific on your system, which can be fixed.
I had similar issues on prior macOS/iOS systems and typically were solved by logging out of iCloud and logging in back. Somehow, the certificates used by the system to authorize connections became invalid for some tools. This can be provoked by system upgrade when more than usual number of things change, but does not need to be.
Try logging out of iCloud - you may need to logout both in system Preferences (which credentials are used for Contacts, which is what Messages are using) as well as Messages and likely FaceTime. You may want to uncheck and recheck various options you have selected there to refresh settings, in case they go corrupted. If it still cannot be sorted out, it may be configuration (plist with configuration) for Messages is corrupted or Keychain is corrupted. There is instructions on like (google it) how to reset those.
In any case, it should be working. Most people have no problems.

Lol its not my machine, its Catalina. I'm using a 16" MacBook Pro and a iPhone 11 Pro Max. The MacBook Pro was set up as new and I have zero issues on my iMac that runs Mojave.

 

[Honza1]

Lol its not my machine, its Catalina. I'm using a 16" MacBook Pro and a iPhone 11 Pro Max. The MacBook Pro was set up as new and I have zero issues on my iMac that runs Mojave.

You can be laughing as much as you want. If this was common, there would be firestorm by now. So this is not common and something went wrong when setting up your system. Happens occasionally...
Do you want to get it fixed or laugh? If fixed, see if logout and login helps. If not, keep laughing and be happy. Good luck.

 

[macnicol]

I have the same problem which started last week, about 7/22/2020, up until then I was able to send photos and attachments, then after a Catalina crash/restart overnight or an auto update to the system, iMessage would not send attachments when drag and dropped to the iMessage window. Tried copy and paste and that doesn't work either.


I have a 2019 iMac 27" with Catalina MacOS 15.5.6. These are files from an external HD, NOT a NAS drive, which have always worked up until last week. Just hangs at the end of the iMessage send progress bar and then gives error alert that message was not sent. I have restarted which did not fix it. I created a new user and logged in as new user which did not fix it either. SO it is a Catalina 15.5.6 update issue. I got a notice from Drive Genius that system files had been changed from the last log in. One of the was a new apple.com iMessage file: com.apple.installer.osmessagetracing.plist

Tried the suggested workaround of dragging the file to the desktop first and then to the iMessage text box and that worked. So iMessage can't access external HDs apparently. This is unacceptable.

Another example of some Apple software hacker changing software without any configuration control or doing regression testing to see if the change they did broke something. Apparently there is NO Software Engineering Management or discipline at Apple anymore. Seems like a bunch of kids just messing around and making whatever change THEY want without regard to the drastic consequences for the end users who have spent millions of man hours learning and depending on the MacOS GUI and functionality. Someone should be in charge of Requirements and Configuration Management to prevent gratuitous changes to the system.

 

[macnicol]

I have constantly had issues with iMessage on Catalina and honestly I'm pretty much done with using it at this point. Messages don't come through sometimes, contacts don't fully sync, and its just overall very buggy. Does anyone have any tips on how to improve it or am I just stick with it like this with Catalina. I have a different device running Mojave and it never has a single issue. Really frustrating.

Dittoo!

 

[Omega Mac]

Yep updated to 10.15.7 introduces a bonus inability to connect to iMessage! It's software and ill tested updates.