Victor Lyapunov wrote:
Thanks for your answer, olli.

As i send mail not from my freebsd server, but rather from the clients
on the local network, so here's what i did:

my pf.conf:
set loginterface pflog0
set block-policy drop
set skip on lo0
block drop log on em0 all
pass log inet proto tcp from 192.168.0.0/24 to any port {smtp, pop3,
imap, smtps, pop3s} flags S/SA keep state
pass log proto udp from any to any port = domain keep state


# tcpdump -net -i pflog0
Now i went to a windows computer and tried to send an email with
attachment to gmail.com (sending failed at 2%)

here's what i got in my pflog:

rule 4/0(match): pass in on em0: (tos 0x0, ttl 128, id 19860, offset
0, flags [DF], proto TCP (6), length 48) 192.168.0.5.1822 >
209.85.129.111.465: [|tcp]


rule 4/0(match): pass out on em0: (tos 0x0, ttl 127, id 19860, offset
0, flags [DF], proto TCP (6), length 48) 192.168.0.5.1822 >
209.85.129.111.465:  tcp 28 [bad hdr length 0 - too short, < 20]

why is the [DF] bit set?

can you try with the following pf option
scrub all no-df

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