New MBP won't load keychain items from old Mac

[Builds]

I have a new MBR, would like to transfer all passwords and WiFi's from old one.
In the keychains folder, I have 5 files:

• login.keychain-db
• login2.keychain-db
• login3.keychain
• login3.keychain-db
• metadata.keychain-db

I have transferred the first 4 files to a USB drive, renamed them, and added them to Keychain in the new MBR. When I go to list of WiFis in network preferences, I only see the one I connected to after installing the new mac. When I try to connect to a server using my FTP client, I get an error that the password is incorrect.

The passwords and WiFis are there for sure, since when I look for them in the imported keychain, I see it's there (I actually took my FTP password from there and used it manually to connect to a server), however for some reason it is not "loaded" onto the new mac in a way that it is being used. I tried deleting and importing again, as well as restarting, nothing works.

Any ideas?

 

[ferrarr]

Keychain syncs through iCloud, are you using the same iCloud account on both Macs? What is the version of OS X on the older Mac?

 

[Builds]

Keychain syncs through iCloud, are you using the same iCloud account on both Macs? What is the version of OS X on the older Mac?

Both Macs have latest Mojave. When I restart the new Mac, I get a notification that iCloud password must be updated to log in. I then input it, and see that Keychain is not activated under its settings. I set it on, confirm using my other device, but still nothing. I went through this process twice in the last 10 minutes.

When I open keychain on my old Mac and choose "iCloud" I see a lot of entires, however on the new one I see only few under iCloud...

Edit: I logged out of iCloud completely and logged back in. It seems to be synced now, meaning I see the names of all the WiFis I connected to in the past, but when I go to the list of WiFis in the network preferences, there's still no listed networks other than the one I am connected to.

 

[MacInWin]

Two different areas. The keychain holds the passwords for when you go to those networks, the list of networks in the network preferences is populated as you use the network. So when you go to those other networks and keychain provides the password, they will appear in network preferences. I don't know of any way to pre-populate that history list in Network preferences.

 

[ferrarr]

Maybe log out of iCloud on the other Mac? Then back in?