iMessages won't send pictures after high sierra update

I recently updated a number of my Macs to High Sierra. One of them now won't successfully send pictures via iMessage to an iPhone. I have tried multiple iPhones with the same result. The iPhone user sees a "downloading" icon like the one pictures below, but never receives actual image. The iPhone has the latest iOS. Any suggestions?User uploaded file

MacBook Air (13-INCH, MID 2011)

Posted on Oct 17, 2017 6:57 AM

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Posted on Jan 3, 2018 9:55 PM

After spending over 5 hours with Apple Support and literally reinstalled everything over, we narrowed it down to a corrupt database within the Library Preferences. So the fix that worked for me was:


1. From your desktop, hold down "Option" and click the Go tab.

2. Scroll down to Library

3. Go down to the Messages folder

4. Take all of the files ending with .db and pull them out of the folder onto the desktop.

5. Restart computer and see if it works. Your messages should generate new files and if it does work, you can trash the old .db files.

22 replies

Oct 31, 2017 1:31 PM in response to devmodenull

Hi,


It can be Little Snitch if this process is not allowed:-

User uploaded file

This tends to pop up if there is a sync around where you have sent something from an iPhone or another device.


Not to be confused with:-

User uploaded file

IMRemoteURLConnectionAgent is the process for Logging the account into the iMessages server.


IMRemoteURLTransferAgent is the actual one for the allowing of sending pictures and files and also seems to be the name of the process in older versions


It can be a block or not allowed in Little Snitch or other Firewall apps.

It can also be down to the DNS servers listed not finding the server.







User uploaded file

8:31 pm Tuesday; October 31, 2017


 iMac 2.5Ghz i5 2011 (Sierra)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 iPhone 6 iOS 11.x and an iPad (2)

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iMessages won't send pictures after high sierra update

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