RE: Anyone Familiar with How Server Farms and SSL Certificates Work?

The odd thing to me is that they seem to be using relatively short term
root and intermediate certificates. I can understand having individual
certs at 3 years or less, but they seem to be doing 2 years on their
root and intermediate. They are the issuing organization, and by only
issuing certs to themselves from those root chains, they can control who
has them and when they have to be updated, but it still seems like they
are making more work for themselves than they have to.




Kevin Bucknum
Senior Programmer Analyst
MEDDATA/MEDTRON
Tel: 985-893-2550

-----Original Message-----
From: MIDRANGE-L [mailto:midrange-l-bounces@xxxxxxxxxxxx] On Behalf Of
Bradley Stone
Sent: Tuesday, December 13, 2016 7:07 PM
To: Midrange Systems Technical Discussion
Subject: Re: Anyone Familiar with How Server Farms and SSL Certificates
Work?

No answer from MS or any other support forums on how or why this is
happening, but I was able to put together a pretty neat little system
using DOS batch files, openssl and the IBM i to constantly log into
their servers with openSSL, saving the Cert retrieved over and over
every 5 seconds. I then compared the certs with one I already had until
I found one that was different and was able to extract the other set of
CAs. It took over 2000 hits for it to finally find the differnent cert.
But I got a few in a row after that.

I'm going to put an article together for it soon just because it was
such a headache. MS... I was always indifferent about them, never
having all these "problems" with Windows like its hip to talk about...
but this was their cloud services... if they can't help paying
customers, I will seriously never recommend their cloud services over
Google's.

Insert in pipe, and smoke. :) Time for a scotch.

Brad
www.bvstools.com

On Tue, Dec 13, 2016 at 8:55 AM, Bradley Stone <bvstone@xxxxxxxxx>
wrote:

I am posting this hear so hopefully someone with some experience can
help me possibly understand what Microsoft's servers are doing.

So, randomly their email servers are presenting different SSL
certificates to clients when they connect. If the certificate used is

one that we haven't imported the Certificate Authorities (CAs) for, we

get an not trusted error on the IBM i.

Normally for this type of thing we simply use openSSL to grab the CAs
and import them using DCM. But because it's random, and the server(s)

that are presenting this odd SSL cert we can't purposely connect to,
it's been a whole day of trying to get this rogue SSL certificate
(hopefully it is only one more!)

The same thing is happening with the RESTful API servers. I got lucky

with openSSL on these and was able to get both certificates so that at

least for those using the API are ok for now.

But the smtp server is another story. I haven't been lucky enough to
get the other certificate.

How and why would this be happening? When they install a new SSL cert

does it get replicated to all the servers in the farm? Or is that
don't manually and it's possible a couple didn't get updated (at

all... or "yet")?

I've tried contacting MS but so far nothing from them. I just want to

know if what I think is happening is in fact happening.

BTW, if you're on the fence between using Google or Outlook 365 for
your corporate email in the future, after dealing with both for a few
years I would pick Google over MS every time. It's faster and much

more stable.

(just a vent there... haha!)

Brad
www.bvstools.com

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