Theory time: Yogg-Saron is the reason that Sylvanas specifically ended up in the Maw after her suicide atop Icecrown Citadel. Moreover, Yogg-Saron may have been the reason behind the Jailer ever being aware of Azeroth and its World Soul.

How does this make sense?
Chronicles Volume 1 states that when the Titanforged began their invasion to cleanse Azeroth of the Old Gods, they began in the Black Empire's Northernmost holdings.
Going off of this map, that suggests that the Titanic invasion began in Yogg-Saron's territory.

Yet, it was not the first of the Old Gods to fall -- and I think there's a good reason as to why this occurred.
Specifically, I think that Yogg-Saron fought back by siphoning off of Death Energy from the Maw. In doing so, I'm willing to bet that it came under the influence (at least partially) of the Jailer, who had now become aware of Azeroth's existence.
What effects would this have had?

First, the power Yogg-Saron siphoned from the Maw is likely what allowed it to gain the ability to kill undead creatures with its blood (Saronite).

Moreover, this is how the vale over Northrend was weakened -- which is how we got Icecrown.
Want more proof?
What form does Yogg-Saron's avatar take place when the God of Death reveals its true form during Phase 2 of the encounter against it?
A Val'kyr. And we know for a fact that this likely wasn't due to it stealing from the Lich King.
Am I saying Yogg-Saron was under the direct control of the Jailer? Probably not.

But it does tie in why Sylvanas ended up directly in the Maw and bypassing judgment by the Arbiter. It also explains the discrepancy with the Titan invasions, and also explains the weakened veil.
It’s also possible that N’Zoth became aware of the Jailer and its plans 10,000 years ago during the Sundering — Azshara was *near* death when N’Zoth rescued her and made the deal that saved her.

I’d be willing to bet that the Jailer would otherwise have tried to claim her.
This would also explain why the Naga (Void affiliated) and the Kvaldir (Death affiliated) seem to fight every chance they get, and also suggests that part of why Death has been so active on Azeroth is because it realises the Void and the Fel are also after the World Soul.
Belated addendum: Rewatching Warbringers Azshara, I almost wonder if Blizzard was trying to provide a silent hint about the aforementioned Azshara-Jailer theory with how the Kaldorei tormenting Azshara are almost explicitly shown to be dead.
While it's possible that this was just a vision N'Zoth inflicted upon Azshara to drive her to despair (prior to offering her bargain), the fact that she *explicitly* references the "darkness" that Sylvanas seeks to unleash makes it sound like she knows about the Maw/Jailer.
On that note, consider when players began hearing *explicit* references to N'Zoth: In Legion.

What else happened in Legion? The machinery of death was broken.

N'Zoth knew about the Jailer's resurgence, and it likely sought to break its bonds specifically out of desperation.

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16 Oct
I will no longer be silent.

If you're curious about why I (and others) are cynical about the WoW team's feedback process, here's a thread about private avenues of feedback that some theorycrafters were/are offered — and why they haven’t made an ounce of difference in a long time
Around early/mid 2013, just before the release of the Throne of Thunder raid, I was invited to a private feedback forum for WoW theorycrafters. This was the first incarnation of the "private forums", which many have speculated about ever since. Image
In its initial stages, this forum was wonderful. Many of the most positive developments in both MoP and even the developmental stages of WoD were the result of the careful, thoughtful feedback that players on this forum provided.
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