I ran into the same problem and got it resolved. To put simply, there are several common causes of the issue.
Why Digest Authentication Fails in Windows 7 Mini-redirector
JUN 2ND, 2014
Here is the problem: you have a WebDAV server, it works with
almost all WebDAV clients except Windows 7 mini-redirector when using
Admittedly, why choosing Digest Authentication and sticking with
Windows 7 mini-redirector in itself might be a debate. This article
does not discuss about design options such as this. It only aims to
share what I’ve learned struggling with the Microsoft’s WebDAV client
so that other folks won’t pay the price in the future.
The usual way to connect to a WebDAV server from Win7 is to open up a
Windows Explorer window, map a net drive to the url of the server. If
the server is protected by Digest Authentication, you will be prompted
to enter your username and password. You type in, submit, and it pops
up another box, asking you for credentials again. You keep typing the
correct credentials 3 times, and Windows will not allow you keep
This is the problem I was facing. Making things more interesting, the
problem could be masked when Fiddler the web debugger is present. That
is to say, whenever Fiddler is the man in the middle, it works;
otherwise, it stops working.
I tried to approach this problem from many directions which I will
cover later in this post, but all didn’t solve the problem.
I was a big step forward when I discovered that Fiddler has two
connection related options: “Reuse client connection” and “Reuse
server connection”, both are turned on by default for peformance
reason I suppose. The working/not working scenarios I described
earlier could be reproduced by toggle “Reuse client connection”
on/off, without shutting down the Fiddler completely.
By comparing the connection patterns of my session with the session
between Win 7 client and Apache, the difference turned out to be that
my WebDAV server always drops the connection, especially upon
returning 400 series of HTTP status code, for example, 401
Unauthorized. The fix is simple, keeping the connection alive upon 401
solves the problem immediately.
My coworker, a seasoned developer, told me this is an ancient bug of
Microsoft, which existed for over 12 years but they never fixed it.
The client starts a TCP connection, C, and then sends a plain HTTP
request, the server will generate a 401 response together with
“WWW-Authenicate” header, including the Digest information, sends it
back to the client. At this particular moment, the server has the
choices to either keep the connection alive, or drops it, regardless
of what the “Connection”, “Keep-Alive” header says earlier. Say the
server decided to drop the connection, when the 401 response get to
the win 7 client, it will compute an “Authorization” header needed for
Digest Authentication, however, win 7 client insists to send this
header along through the connection C created earlier, if C is broken,
it will start a new connection, C’, send a plain request WITHOUT the
“Authorization” header. At this point, you should be able to predict
what is going to happen next and to explain why the multiple login
problems exist ever.
To summary the above process, the Win 7 client will ONLY send the
“Authorization” header upon two conditions: 1. right after you submit
the credentials, i.e. when “Authorization” header was created the
first time; 2. the connection was the same connection through which it
sent the original plain request and got the 401 response.
HTTP is a stateless protocol, neither client nor server should rely on
any states such as the connection status. A robust server such as
Apache with WebDAV module enabled or a robust client such as Cadaver
is able to cope with a rigid client such as win 7 client, or a rigid
server such as my server.
WebDAV with Digest is hard to get right, I only saw two servers made
it right so far, one is the popular Apache DAV module, the other is my
server after fixing this bug.
Win 7 WebDAV support is indeed crappy. There are many other choices
for your customers. Cadaver is an excellent open source WebDAV client
on Linux/Unix platforms, Mac has build-in WebDAV support, and third
party clients such as Cyber Duck, BitKinex, etc. are all good choices.
However, if a large portion of your customers are still relying on
Windows platform thus Win7 mini-redirector is still their most
convenient way to access their WebDAV server, you may still need to
make it work for the customers. Here are some other possible causes
that the Digest Authentication that does not work.
- Your authentication logic is implemented wrong so it won’t accept even
- The DAV response body uses default namespace,
refer to the links below for further details:
- If you are sending “Authentication-Info” header, be sure to make it work If > all sending “Authentication-Info” header, be sure to make it work
of these does not help you, here are some approaches I found useful
when hunting for the root cause: 1. Use Fiddler, ngrep to capture and
study the traffic 2. Use open source clients and servers as base
reference. You could know the machinery of process by reading the
code; the code is well tested and reliable 3. Expand your
perspectives. If HTTP communication does not work, the reason might be
the traffic (content), timeout (timing), connection (context),etc.
4. Remember the old fact: HTTP is stateless. No assumptions should be made based on any states added 5. Read the RFC carefully and do not
hesitate to ask questions online
To wrap up, Digest Authentication is a scheme stronger than Basic.
Basic literally provides no protection in terms of today’s security
technologies and Digest is inherently vulnerable to man in the middle
attack. Please think carefully which security context are you using