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Penetration Testing O365 to/from Azure .Net Services

Posted on 2016-10-27
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Last Modified: 2016-10-31
I have a planned release (multi-product deployment) that might be derailed because some one hasn't got "penetration testing" done (so may not get security clearance) in one important part of the solution.

The only details I have about the scope of this testing is:

Vulnerability Testing will cover Azure/SharePoint for web jobs.

Source O365 (SharePoint) ... Destination Azure .Net Services
Source Azure .Net Services ... Destination o365 (SharePoint)

I suspect that the quality of the .net code may be the biggest issue here, but assume this is written to stringent enterprise standards.

How risky can the "pen testing" be? Is it likely to result in a "no go" decision?
Should I be greatly concerned? or only moderately? or just a little? (explain why if you can)

(nb: I do not know what penetration testing actually does, nor do I know much about .net or Azure)

Thanks.
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Question by:PortletPaul
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btan earned 400 total points
ID: 41863379
Some quick background to set the stage. The idea for security testing is to sieve out known vulnerability in the system and application before commission of the deliverables in production. It normally covers vulnerability scanning and penetration testing.

Vulnerability testing
> Network vulnerability scan - Scan a set list of IP addresses to determine what services are listening across the network, and also what software (including versions of the software) are running. Check for as weak spots such as unsecured services or unnecessary ports that can be further be exploited
> Application vulnerability scanning - Covers mainly two approaches:
>>>Static Code Analysis - Adopt whitebox approach.  If you have the codebase of your application, this will be reviewed against a set of secure coding practices (based on programming language). It is code review in your software development process.
>>>Dynamic Code Analysis - Adopt  black box approach. It probes and scan appl with tools similar to scanners to conduct injections and attempt to crash or bypass appl controls .

Penetration testing can include vulnerability scan and normally that is the case for a preview of the target weak spots. The scan findings will then be used to penetrate into the target to  uncover more flaws in an application or computer system. The objective is to exploit one flaw and further intrude into the appl/system to assess the damage extend possibility. It is not so much tool driven besides for the scanning. A manual process will drive this testing primarily. However, there is caveat to the depth of testing, i.e.
> Not to jeopardise the target being tested causing production unavailability or outage of services.
> Not to include actions such as installing a back door, launching DDoS attacks, or siphon and tamper sensitive real live production data.

Instead the testing should in best practice have consider the engagement as follows
> Verify till the "damage" can be done like retrieve some data will suffice as proof to remediate.
> Use of non-production data such as “flag” in place of “real” data
> Stop when the actual ethical attack has met the concurred target for penetrating into the network or application, w/o further damages.
> Perform these tests against a test or pre-production environment
> Seek expertise from experienced professional

You may want to check out this azure penetration request - https://security-forms.azure.com/penetration-testing/terms
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Author Comment

by:PortletPaul
ID: 41863402
Thank you btan

I am  trying to reach a risk assessment (in particular likelihood of a "no go")

Testing of .Net in Azure talking to SPO365  isn't uncommon is it?
Does it take a long time to conduct?
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Assisted Solution

by:btan
btan earned 400 total points
ID: 41863410
You can have .NET app to "talk" to SP0365, but typically it is via API that is authorized to be interfaced by the appl. There is gateway to inspect the legit calls and ideally comes from a proxy sitting in the middle of the two. They like to use cloud access security broker otherwise the .net appl need to check too, of course.. it does take time but it should be transparent if you have such gateway to get the evidence to check, otherwise you need to see that such check is done at appl and 0365 end.
- audit & track every user activity
- detect & identify account breaches and malicious use
- enforce granular control over all activity and uses
- prevent and detect threats in real time to/from OneDrive, SharePoint and Mail
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by:David Johnson, CD, MVP
David Johnson, CD, MVP earned 100 total points
ID: 41864410
FYI, Azure and Office365 have dedicated RED (attack) and Blue (defend) teams that are continually pen-testing their platforms.
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