> If I set MAC SC 7.4 r27274 to "Automatically start server at login"  
> (default) the server does not start on a system reboot.

You need to log in to your system. Rebooting and leaving it at the login  
prompt will not start it. This is working for me.

Do you have exact steps how you proceed to see this failure? Can you  
reproduce on any system or just some/one?

I will investigate further

I haven't seen this issue in a while now, closing it as fixed

This happens from an Upgrade Install from 7.3.3

While the Control Panel states that SC will 'auto start' it never does.

Install 7.3.3
Set for 'Automatically start at login'
Reboot and Login to MAC to verify that 7.3.3 starts
Upgrade to 7.4-nightly
Launch Control Panel & verify that 'Automatically start at login' has been set by default (do not change anything on this page)
Reboot and Login to the MAC, notice that any player previously attached to the MAC will not reconnect.
Open the Control Panel, notice that Server Status is set to 'start server' The server is stopped

Note: to 'fix' this, I have to:

Select Never start...
Reboot
Select Automatically start at login...
Reboot

now it starts as expected

change 27775 - we need to update startup items during installation/upgrades, as the installation folder might have changed (due to the product renaming)

This bug has been marked as fixed in the 7.4.0 release version of SqueezeBox Server!
    * SqueezeCenter: 28672
    * Squeezebox 2 and 3: 130
    * Transporter: 80
    * Receiver: 65
    * Boom: 50
    * Controller: 7790
    * Radio: 7790  

Please see the Release Notes for all the details: http://wiki.slimdevices.com/index.php/Release_Notes

If you haven't already, please download and install the new version from http://www.logitechsqueezebox.com/support/download-squeezebox-server.html

If you are still experiencing this problem, feel free to reopen the bug with your new comments and we'll have another look.