Not sure why, but really seems like another Apple bug. It seems like this is some issue with really poor iCloud syncing behavior. I will try to report back after this is done to let everyone know if this worked. Sadly I can't completely verify that the images I knew weren't syncing are there until the iMessage Search function finishes indexing my messages. The local storage for iMessages now shows at roughly 20GB (which is expected), and after a few tests, it seems like images are showing up. macOS 12 or earlier: Choose Messages > Preferences, click iMessage, then select Enable Messages in iCloud. Today, I erased the new phone, and set it up using the Direct Transfer function instead of iCloud Backup Restore. Set up iCloud for Messages on your Mac In the Messages app on your Mac, do one of the following: macOS Ventura: Choose Messages > Settings, click iMessage, then select Enable Messages in iCloud. However some images were still empty chat bubbles. This also lead to some images showing as 'Download Image' (I forget the exact text) buttons in the conversation instead of empty chat bubbles, and tapping that downloaded and displayed the image. Which seemed like an improvement, but still lower than I expected (considering that local storage was like 20GB for messages). The next morning this caused the iCloud Messages storage to increase to about 6GB. On my iPad (which had all the data), I toggled the Messages toggle off then on under the iCloud sync settings. 2010-2017 Macbook Air/Pro/Touchbar Efi Firmware Bios Unlock Reset. On a Mac (macOS 10.14 or earlier) or a Windows PC: Open the iTunes app, click the button resembling an iPhone near the top left of the iTunes window, click Summary, then click Restore Backup. I realized that in iCloud it was showing that Messages was only taking up roughly 1GB of storage (which seemed incredibly low). We permanently unlock and remove EFI Firmware and iCloud Passwords on all Apple Mac Computers. Do one of the following: On a Mac (macOS 10.15 or later): In the Finder sidebar, select your iPhone, click Trust, then click Restore from this backup.

Restore imessages from icloud on mac