Several years ago I put an OpenBSD system in as a firewall and mail server at a 
small charity that I volunteer at (kwaccessablility.ca)
that fixed nearly all the problems that they had with viruses, spam etc.

Last year I talked them in to switching to VOIP (on the OpenBSD server using 
Asterisk). Their phone costs dropped from over $250
per month to less than $30 per month (I used the service from unlimitel.ca). 
The change is costs per month made up for the costs 
of the new telephone equipment within the year.

Nearly all their communication that was done by fax is now done by email, 
except for one organization. That organization which is 
run by the city supplies transportation for physically handicapped. That 
organization is insisting on faxes. They will not take email.
The charity currently has an analog fax just for the purpose of arranging 
transportation, and that line is costing over $60 per month.

I looked at email to fax services, but I believe those queue the faxes up and 
send them as time is available.  The charity and
the transportation organization need immediate sending and receiving.  They 
carry out a conversation with hand written
notes (requiring the charity to type the responses would not be a problem).

Asterisk has a fax service, so I thought I could use that. But the Asterisk fax 
sending service requires TIFF in a directory
and receiving service puts a TIFF file in a directory. 

 The charity operates in a Windows environment. To the problem is: how does a 
person (probably a volunteer)
 on a Windows machine put a TIFF file into a directory on an OpenBSD, and in 
addition send the information 
as to where send the fax and get back a status on success or failure of sending 
a fax.

 I don't think receiving the fax will be that much of a problem; it should be 
easy to take the fax out the directory 
and send it as an email to a group mailbox. 

What I don't have is a good to solution for is how the person sitting at the 
Windows machine is to send a fax.
 There are some commercial solutions for Linux, but I have no idea if they 
operate OpenBSD. 
 The commercial solutions are generally of the format that an email gets sent 
and fax is extracted from the text of the message.

I would like to know if anyone has done something similar or any good 
suggestions on what I should do to
get faxing to work

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