As you can tell I am not and never was a fan of Session. But if I would be this is probably the question I would have asked too.
In earlier days they several times published about plans to monetize like here Session: The Road To Monetisation And $oxen Value Capture - Oxen | Privacy made simple. Not sure any of that really worked out.
Adds friction and isn’t coherent with the mission.
Thanks for sharing! I did decide to donate since I love the concept of secure messaging without the need for a phone number. Perhaps it’s me, but I’ve been wondering why Session hasn’t received more attention. Even most of my IT savvy acquintances hadn’t heard about Session when I first mentioned it during the years. If they manage to stay in the game, I hope they will be able to attract more attention. In my ideal world, once “everyone” has migrated away from WhatsApp to Signal, I’ll keep in touch using Signal/Session integration while luring them away from Signal to Session. 
Cause it literally lacks the standard reasonably expected feature set discussed earlier in this thread? It was never a product one could fully move to even if they wanted to and had the contacts for it.
We could technically decentralize Signal too - using our own proxies (or others’). It just won’t be onion routed but could still work where it needs to if not many are connected to each proxy (in order to increase your chances to remain hidden from nation states).
That could be part of the problem. Personally I don’t care much for more than the bare minimum, but to each their own. 
Session partners with Silent Donor to accept anonymous donations.
Nice, but I am not planning to donate 50$ (minimum accepted)
Wow! I didn’t realize there was a $50 minimum. That sucks.
Haha holy.. seems Joe Biden’s security agent isn’t the only one shooting themselves in the foot today.
Do we even know how much money they need?
I thought PFS was removed solely for technical reasons. I never heard Session say they don’t believe in PFS. Do you have any public sources of this claim? Or, since you were involved, can you elaborate on what you heard in the discussions?
For the last time. If you read the actual thread. The tweets in which he stated such are not longer visible, but we did write on it here too. Session messenger adds PFS, PQE, and other improvements
The simple fact of the matter is that Session provides protections against these types of threats in other ways — through fully anonymous account creation, onion routing, and metadata minimisation, for example. These protections will prove as effective, or more so, in many real-world scenarios within Session’s scope and threat model.
(Source)
Session has always claimed that their architecture would protect against this in other ways, mostly due to their onion routing. Which I am very skeptic about most because of their control over the network.
Don’t forget Session also had this bug which is such a critical failure for a secure messaging app that I’ve rescinded my will to donate. Signal it is <3
Not sure what you mean. Are you talking about connecting to Signal with a proxy chain?
FYI I did read the thread, thank you very much, but yes I did miss the part about your discussions with them over X/Twitter. I honestly believed you were involved in Session at a deeper level than just as a stranger.
What you cited doesn’t convince me they don’t believe in PFS. AFAIK they had technical issues implementing PFS over an onion-routed network and attempted to use other measures to compensate for the lack of PFS.
Don’t get me wrong, I find the lack of PFS disappointing too. Additional to what they wrote about their v1 protocol, I can’t find the source any more, one of the Session team said users should create/transition accounts regularly to render the lack of PFS a non-issue. To expect users to manage that while maintaining communication with their contacts is hilarious!
I never said they don’t believe in PFS. Don’t misquote me. They said they don’t believe it is needed (in their setup). You can listen to their CTO saying it here too: Private messaging via Session w/ Kee Jefferys | Opt Out Podcast
They said it is good enough without it clearly. And I deeply disagree with this thought they kept sharing. I really wonder why they suddenly now think that it isn’t enough.
Sorry I misread your post. You stated Session don’t believe PFS is needed, not Session don’t believe in PFS.
I haven’t read any of Session’s recent comments about PFS yet. After Session failed to implement it for several years, I hope they’re not saying anonymous user account creation, onion routing and metadata minimization are not enough to justify not implementing PFS.
I’ve chatted with Session team members on many occasions. In my experience, Session has always been a bit stubborn. As an example, see the chat excerpts in my thread on deterministic file encryption.
Defending their positions and steering their ship behind closed doors. The odd survey or user testing (whose results I’ve never seen) seemed haphazard at best. It’s not a good look; but as a user, the lack of influence on this “open source, closed doors” project is something you got used to.
That said, I should at least praise some of the newer recruits, as they certainly did try to work with me. I can’t imagine what the workplace culture is like.
Mishaps that should’ve been caught earlier, persistent bugs, and attention being paid to external partners as opposed to home-grown contributors — it was okay as long as the service was free.
It’s true; a lot of node operator trust was lost in the SESH pivot, and even before that, in the times when the network was choked out there indeed was an exodus of users (whether it was a particular spammer or a client bug triggering the bad server code, I guess we’ll never know). Still, a lot of users stuck around. For the most part, Session did what it needed to do. Even if we had our complaints.
But Session bit off more than it could chew. Technical debt was accumulating and they weren’t meeting their goals. Even monetization has been on the roadmap for a long time. Of course, the paid tier is set to be largely cosmetic; just like you would expect from a tech startup in the 2010’s. (c.f. SimpleX, whose monetization hinges on providing a tangible service to their customers.)
Even now, the donation page is talking to us like we’re investors. The humility to lay out the issues that have led them here hasn’t arrived yet, and I suspect it won’t ever; not under the current leadership.
They’ve spent all this time projecting an image of confidence. I can’t blame them for being afraid of the consequences of a move like that. We’ll see whether it comes to that.
Session’s audience is now bigger than ever. But even if they acknowledged their stubbornness, restructured their development and commited to doing better — I wonder who, after all this time, would actually listen with an open heart?
And — not that it has any particular impact on the PFS argument — but despite having strayed quite far from Signal, Session did indeed start as a Signal fork. It’s easy to forget that fact.
But that’s just my two cents. 
Thanks for sharing this. You mentioned quite some things that had escaped my attention over the years.
UPDATE: Session will shut down on July 8th unless they receive $1 million dollars in funding.
TL;DR: Session has received enough funding ($65K) to survive until July 8th. However, they estimated that they need at least 1 million dollars a year to keep their operation going.
I hope they survive, but I don’t see how they can raise one million dollars in donations by July 8.
How would you guys feel if Session compromised their values by accepting venture capital to reach their goal?
IMHO, that would be a terrible idea. Their best hope seems to be to get affluent donors to donate anonymously with no strings attached.
This is why cultivating a community is so important. Not that Session didn’t, but they could have done a better job at it. If it was Tuta or Proton in the same situation, I think people would be far more likely to donate, because their services already good enough for people to have confidence in them, even if they are not perfect.
