Mac Music and iPhone can't connect

[sluggo]

Thought I'd plug the phone into the Mini this morning and sync things. My iPhone 8 appears under Devices, but I keep getting the spinning icon with a "Couldn't communicate with a helper application" message. Suggestions?

[Xairbusdriver]

Do you have the latest updates to iTunes and your iOS?
What is the label of the left-hand column in iTunes?
   Mine is "Settings".
      The Sync controls are in the "Backups" area. (see image below)
If yours are different, please post a screen shot of that area.

[sluggo]

Do you have the latest updates to iTunes and your iOS?
What is the label of the left-hand column in iTunes?
   Mine is "Settings".
      The Sync controls are in the "Backups" area. (see image below)
If yours are different, please post a screen shot of that area.

If I remember correctly iTunes is long gone. Everything is under Music in OS 10.15.4. The phone has auto updates on, but I looked at it this morning and there is indeed a 13.4.1 update that was not installed. That's taking place now.
In the meantime I'll attach a screenshot of the Music app.

[sluggo]

Everything is up to date now. Same result.
Screen shot shows the Sync button greyed out. I've submitted a question to the Mac Communities. Perhaps someone there has seen the issue.

[Xairbusdriver]

iTunes is still around, it’s the way I Sync my iDevices. Have not yet updated to 10.15 and never looked at Music.

Is that image a capture of Music or Finder?

In Catalina macOS 10.15, iDevice syncing is done in a Finder window. Details here. Hope that helps. Hope I remember, when I finally update to the current 'cat'.

[sluggo]

iTunes is still around, it’s the way I Sync my iDevices. Have not yet updated to 10.15 and never looked at Music.

Is that image a capture of Music or Finder?

In Catalina macOS 10.15, iDevice syncing is done in a Finder window. Details here. Hope that helps. Hope I remember, when I finally update to the current 'cat'.

The screenshot is of Music. There isn't even an iTunes app in my applications folder these days.
I opened a new Finder window and did indeed see my phone in the sidebar. Guess what? Same result. See screenshot.

[Xairbusdriver]

As I said, I don't have Music, nor Catalina.

However, does the "iCloud" System Pref have "Music" in the list of apps that use iCloud? If it does, are there any "Options" for it? And, make sure it (Music) is enabled, of course. Lastly, make sure your iPhone is directly connected to the Mac, not through a charging port of an external USB hub.

That's it, I have no more suggestions and cannot use apps/OSs that I don't have. Sorry.

Only other option I can think of is to re-install Music, probably from your Recovery Drive.

[sluggo]

iCloud backup was turned off on the phone. So when I turned it on I'm told that the phone will no longer automatically backup to my computer.
Not sure if this is part of the problem or not. We'll let it go this way for a day or two and see what happens.

[Xairbusdriver]

Back in iTunes and I assume in Music, they are Radio buttons, which means only one can be used at a time.

Probably before you were born, some radios, usually in cars, actually had buttons to select a station. I think it was Chrysler Corp that first had them. They were actually physical buttons, of course! No "touch screens" back then! When you pushed one, any other one that had been selected would pop out. I suppose it was a bit safer than twirling a dial while driving! The owner could set each button to any station they wanted, or, like me, set all five to the same station and frustrate any passenger who didn't like my choice! At any rate, some one at Apple thought those were a good method of selecting one of several choices and cleverly named them "Radio Buttons".

[sluggo]

Back in iTunes and I assume in Music, they are Radio buttons, which means only one can be used at a time.

Probably before you were born, some radios, usually in cars, actually had buttons to select a station. I think it was Chrysler Corp that first had them. They were actually physical buttons, of course! No "touch screens" back then! When you pushed one, any other one that had been selected would pop out. I suppose it was a bit safer than twirling a dial while driving! The owner could set each button to any station they wanted, or, like me, set all five to the same station and frustrate any passenger who didn't like my choice! At any rate, some one at Apple thought those were a good method of selecting one of several choices and cleverly named them "Radio Buttons".

Actually I've owned several vehicles with the type of radio you mention. My first ride was a 1969 Chevy pickup.
The problem still persists with Music not wanting much to do with the iPhone 8. Today a new iPhone SE should arrive so I'm hoping that I can migrate all my stuff to the new phone via iCloud backup.
Apple has an article about opening a new Finder window and backing up or syncing that way. But the result is the same as trying with the Music app.

[sluggo]

As it turns out I didn't need the iPhones to connect to anything concerning the desktop computer. Took the SIM card out of the old and inserted into new phone. Followed onscreen prompts and the phones did all the rest. They completed the transfer themselves.
I wish everything was that easy.