I work from home a lot, and have my work email setup on my home machine with Outlook. Would like to also access my Calendar (in particular) without having to go through webmail interface.
Does Outlook/Exchange Server allow this? Can’t figure it out.
Not likely.
Glance in Outlook under Help/About Microsoft Outlook. If the second line reads “Internet Mail Only”, then Outlook is configured to act as a POP3 client (like most Internet mail readers) rather than an Exchange client (like your computer in the office, most likely).
If that’s not the case, and it says Corporate or Workgroup and you are configured as an Exchange client (from home), then either your company’s network security lacks alot to be desired or you are using a VPN - in either case, you should have access to your calendar already.
As a POP3 client, you cannot get access to your calendar.
Short of using a VPN, the web interface may be your best bet.