Only one respective recipient shows only partial iMessages on iPhone 8 Plus

old Messages on my MacBook Pro, MacBook Pro 13 early 2011 not syncing on iCloud , please see the attachment from iPhone 8+ and MacBook Pro 2011. Both messages are for the same person!

As you can see that that First Message on MacBook Pro, MacBook Pro 13 early 2011 IS 6/23/12, 11:20AM.

However the first message for same person on iPhone 8 plus is Friday Jan 1, 2021.

For privacy reasons, name and pictures of the subjects have been removed. I random check another user on both devices and this is the result. And as you can see that the date matches for the first messages that tells me that for some odd reason only subject-1 old messages from MacBook Pro early 2011 are not syncing if that make any sense!!!!

result matched, the configuration is same on both devices! iPhone 8 plus restored from latest iCloud backup, MacBook Pro restored from latest time machine backup!

Any ideas?????

I had the home number and iPhone number listed so I deleted the home number now. In addition icloud account was name@Cloud.com. I deleted that too, since the person uses name@gmail.com as Apple ID I deleted name.iCloud.com and listed name@gmail.com as iCloud account Apple ID.

just to reiterate, on may MacBook Pro early 2011 the iMessages app configuration matches with iPhone 8 Plus iMessages app, new messages on either device show up perfectly however old iMessages from a specific date on MacBook Pro early 2011 are not syncing for one specific user on iCloud?

iOS version :14.4

macOS High Sierra Version 10.13.6

sorry about the confusion, the problem, old messages, for one specific user, on my macbook pro early 2011, are not syncing on iCloud only new ones are? baffling issue? I am willing to talk on the phone too!!

Please se my comments below.

Yes.

Yes

its not critical issue but troubling why its happening?

will do, thanks!