[...] I feel like there's probably a solution for whatever setup you have.
There is a simple solution to my issue: Don't forget to plug in the external drive before synchronizing the iPhone.
My iTunes library files reside on the system drive, as does all my music, but TV shows and movies are on an external drive because there's not enough room for them on the laptop's internal storage. To add them to iTunes I just unselected "Copy files to iTunes media folder when adding to library" and dragged them in from the external drive. That way I have only one iTunes library, which opens even if the external drive is not connected. Music and cloud-based content play fine without the external drive, it's only a problem if I forget to connect it before synchronizing the phone.
Yeah just tried the Apple Script work around and it makes no difference - iTunes still points to an iTunes folder on the local drive, so I have to go to Advanced and change it to the external drive.
Soli said: I used Automator to delay the start up of every app that needs to connect to data on my external RAID. The apps will still launch if the external RAID doesn't show up and I have to give it 2 minutes, just to be safe. It works and I rarely have to restart my headless Mac mini, but it's not as slick as I'd like it be. Ideally I'd like to be able to have those apps not launch at all until the external RAID is ready and then launch those apps right away.
Do you know if Startupizer 2 has that option? [edit: I just downloaded and ran the app. Adding an external drive as a conditional item isn't an option].
PS: Do you also know of any apps that will stop other apps as soon as a network change is detected? Specifically, I'd like for all of Apple's services to not try to sync when I'm at, say, a coffee shop and need to connect my VPN. I'd like that the local network be allowed to send me a splash screen to authenticate to let me out, then allow my VPN to connect, and then my Mac can let all those other services do their thing.
Also, if anyone knows of a way to stop macOS from delaying for Spotlight or file-dialogs until the external spins up... this has driven me nearly mad for years (some might say it has). Even if it needs the information on the external drive, it shouldn't just hang there until it is online. This seems especially true of Spotlight, which *should* be referencing an index.
Yes, the VPN thing is quite annoying and a security hole.
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My iTunes library files reside on the system drive, as does all my music, but TV shows and movies are on an external drive because there's not enough room for them on the laptop's internal storage. To add them to iTunes I just unselected "Copy files to iTunes media folder when adding to library" and dragged them in from the external drive. That way I have only one iTunes library, which opens even if the external drive is not connected. Music and cloud-based content play fine without the external drive, it's only a problem if I forget to connect it before synchronizing the phone.
Yes, the VPN thing is quite annoying and a security hole.