I updated my profile picture quite a while ago, and it shows my new image on all of my devices, yet when it gets sent to others via contacts or iMessage it shows up as the image I first put in there. Why is this?
How can I ensure that is actually is updated, even though from everything on my side, it appears that it already is?
See the article Add or change contact pictures in Contacts on Mac - Apple Support
The iCloud profile picture Select your Apple ID picture on Mac - Apple Support is from Mac system preferences it can be edited and changed also if you edit from iCloud.com Change your Apple ID profile picture on iCloud.com - Apple Support and its quite different and confined and will not match the picture you uploaded in contact card ( your card ) Set up your My Card in Contacts on Mac - Apple Support
It depends on you to save same picture on both .
Right. I've set all of those already. As I said in the OP, all of my devices (as well as My iCloud ID, Family Sharing, My Card in Contacts...) show the updated picture. But my wife just reset her iPhone recently, and when redownloading her contacts, it updated to my old iCloud image (which she's never even had on her phone to manually set herself). I've also seen my old image in an iMessage chat screenshot from a friend.
I set my profile image on my phone, and it updated automatically when I got my new Mac, so I know it's in the cloud. Yet for other people it still seems to show the old image.
I also have this problem. When i send messages, it shows my profile picture as the last one I set, not the current one. I noticed that my current profile pic is on my gmail.com account, but it is my cloud profile picture I need to change.
This is my problem as well. Apple sold out to Google after iOS 6, and it’s still there. Actually, Apple is now just a google slave.
I set my profile image on my phone, and it updated automatically when I got my new Mac, so I know it's in the cloud. Yet for other people it still seems to show the old image.
When same Apple ID and password say example1@icloud.com is signed in between iPhone and Mac on the same network , if you update the profile pic on iCloud.com or Mac it is mirrored in iPhone .
The other people have different mail address with different account credentials and they can't use your Apple ID account credentials , however in contacts / messages when you edit them the pic is saved in it and other people chat with you view your contact image and not profile image .
The function of profile image and contact image are quite different things .
When your wife reset the iPhone all settings are erased , the iCloud account is set and she is using same Apple ID and password of yours the contacts were previously synced with iCloud and saved and the same contact image will appear .
As you mentioned - it updated to my old iCloud image .
Once again the same Apple ID and password is used in iPhone so profile image of Mac will be same as in iPhone .
iCloud profile picture still sending old one to contacts.
