Doh.  I think this may be what killed me right here.  I had setup tagging on my 
laptop, with the port set to switchport access vlan 101.  In retrospect, what 
you're saying makes perfect sense - I guess I know what I'll be trying tonight. 
 By the way, if anyone has seen a document detailing using PFSense on a 2950 
from scratch, a link would be awesome.

I'm sure I'll have more questions, but everyone's assistance so far is greatly 
appreciated.

~Nathan

-----Original Message-----
From: RB [mailto:aoz....@gmail.com] 
Sent: Monday, February 09, 2009 4:43 AM
To: support@pfsense.com
Subject: Re: [pfSense Support] VLANs/802.1q Trunking

On Mon, Feb 9, 2009 at 02:17, Aarno Aukia <m...@arska.ch> wrote:
> You need to configure the interface on the 2950 to your pfsense box as
> a trunk to send and receive tagged packets.
> e.g.:
>
> Interface fastethernet0/6
>  switchport mode trunk
>  switchport trunk encapsulation dot1q

Ditto, but make sure that if you're tagging packets on the laptop as
well to set it as a trunking interface also.  By using "switchport
access", you're telling the switch to drop tagged packets and place
any untagged ones on VLAN 101.  This is right for end-point ports - it
is unwise to allow your client devices to freely tag however they see
fit.

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