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Working for me on all my encrypted drives.

Did have some wonkiness at first. Disk Utility to mount, get the prompt for password/key, click the "save to Keychain" box. Second time mounting, got the Keychain prompt for "xxxx needs to access your Keychain": if do a enter/return after typing account password, will do a simple "Allow". The next time this happened, made sure to click "Always Allow" and has been working perfectly since.

So, might want to pull up Keychain Access, find the entry in login keychain, then click on the "Access Control" tab to see what checkboxes are on/off and if Disk Utility is in the list of who can use the entry (can add Disk Utility via same dialog).
 

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So, might want to pull up Keychain Access, find the entry in login keychain, then click on the "Access Control" tab to see what checkboxes are on/off and if Disk Utility is in the list of who can use the entry (can add Disk Utility via same dialog).

What are the apps that are listed for you as 'always have access'?
 
CS and APFS are stock Apple processes for Core Storage (aka HFS+ encrypted volumes) and APFS encryption respectively.

If not there, delete the Keychain item and try again.

Disk Utility does not need to be there, just makes for life easier when using Disk Utility.
 
CS and APFS are stock Apple processes for Core Storage (aka HFS+ encrypted volumes) and APFS encryption respectively.

If not there, delete the Keychain item and try again.

Disk Utility does not need to be there, just makes for life easier when using Disk Utility.
OK cool. Mine did look like that but I've deleted it and will try again later...
 
I have had weird auto mounting issues in the past. I now use Auto-Mounter and haven’t had problems since.
 
I’ve been through a few restarts now and it’s still an issue. The encrypted partition won’t auto mount.
 
Are you using this with USB connected drives or network shares?

Network shares. I have never had a problem with USB connected drives.

I have two Synology diskstations. A couple of major macOS versions ago I was getting problems where mounting was intermittent and then finally wouldn’t auto-mount at all. Reading around it looked like Apple removed a key feature that would allow this to happen, but I could never definitively figure it out. I just got sick the hassle of it all and so purchased AutoMounter, this solved all my problems and I have stuck with it since.
 
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