alert if application isn't running
IMO your best bet would be to use launchd to make sure that OneDrive is always running no matter what.

(launchd is a bit like cron but much more powerful.)

Save this file as ~/Library/LaunchAgents/com.tjluoma.keep-onedrive-alive.plist (where ~ is the home directory on the secretary's computer):

&lt;?xml version="1.0" encoding="UTF-8"?&gt;
&lt;!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd"&gt;
&lt;plist version="1.0"&gt;
&lt;dict&gt;
    &lt;key&gt;KeepAlive&lt;/key&gt;
    &lt;true/&gt;
    &lt;key&gt;Label&lt;/key&gt;
    &lt;string&gt;com.tjluoma.keep-onedrive-alive&lt;/string&gt;
    &lt;key&gt;Program&lt;/key&gt;
    &lt;string&gt;/Applications/OneDrive.app/Contents/MacOS/OneDrive&lt;/string&gt;
    &lt;key&gt;RunAtLoad&lt;/key&gt;
    &lt;true/&gt;
&lt;/dict&gt;
&lt;/plist&gt;


Then load it in launchd using this command:

launchctl load ~/Library/LaunchAgents/com.tjluoma.keep-onedrive-alive.plist


That will:

a) Launch OneDrive

b) Re-Launch OneDrive if it is quit or crashes. Basically anytime it stops running, it will automatically start again.

Note that you should UN-check the option in OneDrive's preferences to open at login, because launchd will be in charge of running it.