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I used the iPhone Migration Tool to move from the X to the 11 Pro.

Summary: Not all user-ids and passwords were migrated over. It appears to be dependent on the app security permissions. Migration was completed in 30 mins. Your mileage will vary depending on the number of apps and photos that have been migrated.

Important: Do not erase your old phone until you verify the migration completed successful.

Here is my feedback:
  1. The first time I attempted the migration, it failed. The software prompted me to do a factory restore on the 11 Pro.
  2. After the 11 Pro factory restore, I attempted the migration again. This time it ran without issues.
  3. Passwords
    1. Non financial app user ids/password were migrated over with no issue.
    2. Financial apps were a pain.
      1. I had to re-enter all user-ids/passwords and re-enable face ids for the financial apps.
  4. Two Factor Authenticator Apps (Lastpass, Google)
    1. I use Lastpass and that was a pain. The two factor authentication settings for the apps did not migrate over. I had to un-enroll all apps from two factor and re-enroll it on the new phone
  5. Email app client
    1. I use Outlook app as my mail client.
      1. My user id/passwords did not migrate over. I had to sign back in.
  6. Google Photo App
    1. I had to sign back in.
 
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No idea how my watch is different. I have the series 4. Once the migration of my phone was complete, it brought up a box and asked if I wanted to migrate my watch. I said yes...it was super easy. It did not do that for my wife’s series 3.
 
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My watch was transferred to my new phone, I did not think it worked, but I got a message on the watch asking me if I wanted to use it on my new iPhone 11 Pro Max. Worked like a charm.

Had to redownload all my pocketcasts, which is a pain, however, everything was in the exact same order and archived like my old phone.
 
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My watch was transferred to my new phone, I did not think it worked, but I got a message on the watch asking me if I wanted to use it on my new iPhone 11 Pro Max. Worked like a charm.

Had to redownload all my pocketcasts, which is a pain, however, everything was in the exact same order and archived like my old phone.

Yeah was a good 10-15 minutes of using my phone after the migration before my watch prompted me to transfer to the new phone.
 
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I did several phones this weekend. I didn't use the data migration tool - I used iCloud and iTunes backup/restore. My results with iCloud were not great - one of the backups was corrupt in some manner and a lot of apps and data were lost. I was able to go back to an earlier iTunes backup and sync most of the lost data from iCloud, which was a lifesaver. I recommend that everyone turn on iCloud sync for everything.

The other thing I wanted to mention is that even with iTunes the results with various apps varied a lot. Some came over totally completely, still logged in. Others weren't logged in but FaceID quickly logged me into the app. But there were some where the user ID and pw had to be manually entered. Because it was so variable I'm assuming it's more an issue of how the app was written than how iOS and/or Apple's backup process functions (but I could be wrong about that).

ETA: HobbesInVA's post is excellent and a lot more detailed than I could regurgitate. I will note that some of the financial apps I use did come over nearly whole - just had to reauthorize FaceID, but the user ID and pw were still in Keychain and were autofilled.
 
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I used the migration tool and it worked fine for me. Your apps get downloaded from the app store while the data gets migrated over. The only gripe I have of the migration tool is that it migrated all my photos and videos even though I use iCloud Photos and it filled up the space on my phone. So ever since 11 am eastern this morning its been re-uploading the photos to icloud (don’t understand the logic of migrating all pictures over then re-uploading to the cloud). If anyone has any idea why it works that way let me know.
Same issue. First time I did using the migration tool, and it seemed like my iPhone was trying to reupload every photo back to iCloud. I got scared that it was duplicating everything, so I wiped and started over doing a backup from iCloud. Now, instead it's stuck saying it's downloading my photos, but the number never moves.
 
I did several phones this weekend. I didn't use the data migration tool - I used iCloud and iTunes backup/restore. My results with iCloud were not great - one of the backups was corrupt in some manner and a lot of apps and data were lost. I was able to go back to an earlier iTunes backup and sync most of the lost data from iCloud, which was a lifesaver. I recommend that everyone turn on iCloud sync for everything.

The other thing I wanted to mention is that even with iTunes the results with various apps varied a lot. Some came over totally completely, still logged in. Others weren't logged in but FaceID quickly logged me into the app. But there were some where the user ID and pw had to be manually entered. Because it was so variable I'm assuming it's more an issue of how the app was written than how iOS and/or Apple's backup process functions (but I could be wrong about that).

ETA: HobbesInVA's post is excellent and a lot more detailed than I could regurgitate. I will note that some of the financial apps I use did come over nearly whole - just had to reauthorize FaceID, but the user ID and pw were still in Keychain and were autofilled.

Thank you for the kind words. I don't use Keychain and that would explain why the user-id/pw didn't come over. Good to know. :)
 
Thank you for the kind words. I don't use Keychain and that would explain why the user-id/pw didn't come over. Good to know. :)

FWIW/FYI, an iTunes backup needs to be encrypted to include Keychain, Health and some of the other security-sensitive data on your phone. In theory iCloud backups do the same but my iCloud backups were corrupt. Thankfully I had a very recent encrypted iTunes backup to use.
 
It took me 12 minutes to transfer 34GB of 64GB to the new phone. I didn't have Wifi and only have one sim card and one cheap lightning to usb adaptor (bought it for piano). Don't select "language" in the new phone screen.
 
It took me 12 minutes to transfer 34GB of 64GB to the new phone. I didn't have Wifi and only have one sim card and one cheap lightning to usb adaptor (bought it for piano). Don't select "language" in the new phone screen.
I’m pretty sure it uses peer-to-peer WiFi so you don’t need a network or cable.
 
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