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Two things concerning iMessages. I’ve yet to see anything on security. The old way iMessages worked was end to end encryption with a message composed for each Apple device. How does the new method keep messages secure both in transit and when stored?

Also, do you have to turn on the message archiving to get messages to delete across devices? Or can you just turn on the deleting across device feature. I really only want messages to be deleted. I don’t want Apple to archive all my messages.

Messages don't just lose encryption because they are stored.
 
I don’t think my understanding of the old way was flawed. Messages are encrypted end to end. The sender creates one message per device the recipient uses. It suffers from a man in the middle weakness. So you are right you have to trust Apple. If they inserted a bogus Apple or NSA device as a recipient I’d never know.

I don’t think the new way is as simple as just deleting the encrypted message stored in Apple’s servers. If that were the case then you couldn’t get old messages for a new device since messages are created and encrypted when sent for each device. The sender wouldn’t have knowledge of an iMessage device that doesn’t yet exist.

You are imagining the sender has all of your public keys and sends to each one. This isn't true. Apple sends to each one. You adding a device or three doesn't send the public keys to everyone on your contact list.

I get that you aren't comfortable contemplating the consequences of this design. But it is true.
 
Holy moly how have you managed to fill up 256 GB? I’m impressed!

176gb of music, 20gb of photos (that I'm hoping is due to a screw up with Google Photos, and will correct itself once I'm on wifi), 10gb of apps or so.

I was actually hoping Apple would have done a 512gb X. Then maybe I could have my movies, too.
 
https://m.imore.com/how-to-back-up-icloud-photo-library
“Apple's iCloud Photo Libary service works flawlessly to sync and back up your images and video to iCloud”

Yes, iMore says all sorts of silly things, as opposed to what Apple says themselves:

Back up your photos and videos
When you turn on iCloud Photo Library, your photos and videos automatically upload to iCloud. They're not duplicated in your iCloud backup. But we always recommend that you keep back up copies of your library. You can download your photos and videos from iCloud.com to your computer and store them as a separate library, transfer them to another computer with Image Capture or Photos, or store them on a separate drive.
 
Waiting for macOS 10.13.5 to get the most out of Messages in iCloud.
And I just saw iTunes gets an update as well.
 
What happens when you have different units. Iphones, computers, Ipads when syncing iMessages to iCloud? My units aren't perfectly synced today. Will the missing messages on each unit merge and sync into one complete version or will it sync the least complete unit and consider the missing messages as deleted? Im scared to turn it on if that could mean that I lose a lot of iMessages???

I have several iPhones, computers and Ipads with numbers in different countries. Hence the sync problems between units.

I have years of iMessages on my units and I definitely dont want to lose any of them.
 
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Messages don't just lose encryption because they are stored.

Right. The old system stored encrypted messages on Apple’s server. But the old iMessages had per device end to end encryption. How is the encryption handled now?

You are imagining the sender has all of your public keys and sends to each one. This isn't true. Apple sends to each one. You adding a device or three doesn't send the public keys to everyone on your contact list.

I get that you aren't comfortable contemplating the consequences of this design. But it is true.

The sender creates an encrypted message for each device. Yes Apple sends it in terms of the communication all occurs over Apple’s network. Yes, you adding a device does cause Apple to send every public key you have to the sender’s device. It doesn’t send it to everyone on your contact list. It does send them to everyone who iMessages you.

From Apple’s security document:

How iMessage sends and receives messages

Users start a new iMessage conversation by entering an address or name. If they enter a phone number or email address, the device contacts the IDS to retrieve the public keys and APNs addresses for all of the devices associated with the addressee. If the user enters a name, the device first utilizes the user’s Contacts app to gather the phone numbers and email addresses associated with that name, then gets the public keys and APNs addresses from the IDS.

The user’s outgoing message is individually encrypted for each of the receiver’s devices. The public RSA encryption keys of the receiving devices are retrieved from IDS. For each receiving device, the sending device generates a random 88-bit value and uses it as an HMAC-SHA256 key to construct a 40-bit value derived from the sender and receiver...
 
It’s irritating that airplay 1 is able to play to multiple devices on macOS, but with airplay 2 I can’t send to multiple airplay 1 devices from my iPhone. Some of us have $100+ speakers that are a few years old and probably won’t be updated for airplay 2 *cough*iHome*cough*.

It’s not a huge deal since I usually stream from my Mac, but it’s just a money grab.
Yeah, what the hell. I'd hoped to be able to stream to my new Apple TV and AirPort Express simultaneously from my phone the way I can with iTunes. Lame.
 
Yes, iMore says all sorts of silly things, as opposed to what Apple says themselves:

Back up your photos and videos
When you turn on iCloud Photo Library, your photos and videos automatically upload to iCloud. They're not duplicated in your iCloud backup. But we always recommend that you keep back up copies of your library. You can download your photos and videos from iCloud.com to your computer and store them as a separate library, transfer them to another computer with Image Capture or Photos, or store them on a separate drive.
As I said before, it’s better than not having it on. If my phone breaks or gets lost, I still have access to my photos.
 
messages in iCloud though has been tied to having two factor authentication enabled which is a total pain in the ass so no thanks. i'm not interested in having to enter a passcode every time i pick up my ipod touch or ipad mini at home every 10 minutes or whatever. this whole hyper security era is quite annoying.
 
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