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On 27 September 2020, conflict reignited over the semi-autonomous region of Nagorno-Karabakh. It is stated that this most recent fighting was instigated by Azerbaijan (Source).

Furthermore, Armenia is most definitely protected by the Collective Security Treaty Organization, the foremost power of which is Russia, which maintains a strong military. While Azerbaijan originally was also part of this organization, it left in 1999.

As it turns out, Putin ruled that the conflict did not trigger a obligation of defence, as the fighting was technically taking place outside of Armenia, despite the direct engagement of Armenian forces. However, this does not seems like a forgone conclusion. Putin could have imaginably sided quite differently, leaving Azerbaijan to face the wrath of Russia.

Is there anything to clarify this seemingly risky maneuver?

One possibility is that Azerbaijan simply was willing to face the consequences, even Russia did intervene.

Another possibility is that Azerbaijan was confident it could prosecute the conflict because of Turkey's support for their cause.

One final possibility is that Azerbaijan received some sort of tacit indication from Putin that Russia would not intervene ahead of time, leaving them free to move.

It is worth noting that these can all be combined, they that were willing to begin with, emboldened by Turkey's aid, and received some indication that Russia would not intervene. But perhaps someone has better sources indicating these speculations?

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    Re: "most definitely protected by the Collective Security Treaty Organization" — Member states of this "treaty" are happily fighting each other. A so-so protection, to say the least.
    – bytebuster
    Jun 4 at 21:38
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    Russia was less than 100% happy with the Armenian government following the 2018 "velvet revolution", so that may have been a factor, probably not decisive though. We should also check a common motivation for eurasian conflicts. The contested region lies on a potential westward pipeline route (bypassing Georgia, saving some money for Azerbaijan and Turkey).
    – Pete W
    Jun 4 at 23:45
  • @bytebuster that sounds like the start of an answer :) Jun 5 at 18:06
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Article 4 of CSTO:

In case of aggression commission (armed attack menacing to safety, stability, territorial integrity and sovereignty) to any of the Member States, all the other Member States at request of this Member State shall immediately provide the latter with the necessary help, including military one, as well as provide support by the means at their disposal in accordance with the right to collective defence pursuant to article 51 of the UN Charter.

Karabakh is not recognized as Armenian territory, nor an independent republic for that matter. Since it is considered Azerbajan territory, no aggression to Armenia happened in the scope of CSTO. Individual attacks against Armenian armed forces on Armenian territory DID take place, however, Article 4 also states that intervention can happen at the request of an attacked member state. Other member states do not reserve the right to independently decide to intervene. However, Russia issued statements multiple times, that there are grounds for Armenia to invoke Article 4, and request military intervention, but has not done so.

This particular behavior is one of the accusations levied against Pashinyan by his opposition as proof of conspiracy and betrayal. If proven to be true, it may also be the reason that Azerbaijan attacked (i.e. struck a deal with Pashinyan)

One possibility is that Azerbaijan simply was willing to face the consequences, even Russia did intervene.

Unlikely. No one is suicidal. No country would take such a risk.

Another possibility is that Azerbaijan was confident it could prosecute the conflict because of Turkey's support for their cause.

More likely, and Turkey did in fact intervene. However, this is still very risky. My opinion may be biased, so I will not start comparing Turkey's military to Russia's, however, one thing is certain: Even with Turkey's support, if Russia attacked Azerbaijan, most of the conflict would have taken place in Azerbaijan and they would have suffered the most damage and losses.

One final possibility is that Azerbaijan received some sort of tacit indication from Putin that Russia would not intervene ahead of time, leaving them free to move.

This is speculation. However, if this had happened, I do not see any reason what Russia would have intervened at all, and prevented Azerbaijan from conquering all of Karabakh. So this now seems highly unlikely.

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    So to summarize, it seems that, rather than the other options in the question, Azerbaijan bet that Armenia wouldn't invoke the alliance, (which because it didn't occur on Armenian territory, didn't autotrigger). Azerbaijan was confident of this because Armenia was attempting to politically move away from Russia (And asking for help would have entailed some sort of political restitution).
    – code11
    Jul 28 at 17:53

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