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 My Controversial Tech Picks:

Mint over Ubuntu
LibreWolf over Brave
MPV over VLC
AnonAddy over SimpleLogin
Session over Telegram/Briar
MetaGer over Duckduckgo
SimpleX over Signal
Gossip over Iris
onlyOffice over LibreWriter
KeePassXC over all mobile 2FA
XMPP over Matrix
Monocles over Conversations
AntennaPod over iTunes
Trocador over exchanges with accounts
Feather over official GUI
Farside over LibRedirect
scp command over NextCloud
KVM Virtmanager over Oracle VirtualBox
And of course, Nostr over Mastodon

Add on to my list with your picks in the comments!
(Or dispute/ask why I made a choice) 
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 Yeah, why session over briar? You've brought up publicly the problems with session and big rooms, briar is p2p with forward secrecy.

Trocador... I like trocador. But there's nothing stopping them from logging everything, they could be a honeypot. Their monero bridge is great, unless theyre using it to make themselves valuable to people who want to know what you're doing.

I've never liked libredirect, I found it cumbersome. I use Redirector, a web extension for ff and chromium that automatically changes URLs based on predefined patterns written in regex. On desktop I use my own tool with qutebrowser that does something similar to be found here https://codeberg.org/mister_monster/qutebrowser-url-mutator 
 Briar requires both parties to be online and both to add each other to even begin talking.  This makes it extremely likely that you’ll have to use out of band, or non-Briar communication to coordinate when you’ll be doing Briar.  On the other hand, Session has a model similar to Nostr with nodes for offline communication and you can initiate first contact on Session.

The main difference between Nostr and Session is that Session’s nodes are darkweb onion routed and with Session it goes to the receiver's node while as Nostr the poster picks the node.  Session is not good for forward secrecy that’s correct, but it’s #1 for censorship.

Regarding the 2 browser extensions.  I will check it out.   I see your codeberg here, looks good.  When you visit websites with Qutebrowser, does it show up to the website fingerprinting you as Chrome?
 
 So the rendering engine is qtwebkit, it should look like safari or epiphany browser to everyone. I forget what the user agent string says by default, I've changed it. 
 Why Mint over Ubuntu? I've only ever used Ubuntu...but I'm not married to it. 
 Mint is basically Ubuntu without snaps.  Snaps are universal cross-platform, but at the expense of being slower to open.  The majority of Ubuntu software works on Mint.  There's other reasons but this would turn into a novel.  Maybe we can make an article on this topic?  Would that interest you?
 
 Definitely! 
 Mint is faster than Ubuntu, it's running like a dog on any hardware.  
 can you do a one sentence on why for each 😅 
 Yes, I can on another post.  It would be a good article more so.  A lot of them would require 2-3 sentences though 
 Doesn't mention LibreOffice, Mint over Ubuntu... Debian, Gentoo, Fedora there's plenty options an a never ending discussion so use what you like. MPV on Linux is the only option since there's no MPC-HC lol. LibreWolf and Thorium over Brave and others. 
 You can put VLC on anything, even windows.
I meant Mint over Ubuntu as they are close competitors for the same niche of new users.  Gentoo and others are targeting a different demo for different purposes.  LibreWriter is LibreOffice, sorry if this was confusing.
 
 Mpv or mpv.net can be used on windows too but still prefer mpc-hc since is still maintained in a repo also why I prefer mpc easy has better clarity and colors when displays a video this is very technical but that's what it is 😆 
 Why annonady over simple login? 
 SimpleLogin is hosted with Protonmail and should be viewed as an extension of it.  Proton cooperates with thousands of law enforcement requests and should be viewed as a corporation and not a just open source software that’s just code.

On the other hand, AnonAddy has a better UI, better reputation, seems like just 1 developer which is more hipster, Greenhost is a more trusted host by me, and is more representative of a FOSS project.  You can self host it, and F-Droid has apps for it by different random developers.  SimpleLogin uses Coinbase as a crypto payment provider, which blocks Tor and is going to get the transaction run through an anti-fraud (and therefore anti-privacy) surveillance tool.  

I do not support crime, I but do support a decentralized internet.  Protonmail & Coinbase are more centralized than a lone hipster with Greenhost and Globee.
 
 That's a great explanation and gave me some things to research 🙏 
 You should really use rsync instead of scp. Or if you want some syncing automation, use syncthing, it's very easy to setup.

Your choices over messaging apps are a bit all over the place. You need to meet people where they are, otherwise you'll talk to no one. What you can have is a ranking of preferences.

I could nit pick more, but most picks are solid! 
 Rsync is whole software , not 1 file to send someone.   Syncthing is good for among your PCs, again not sending someone 1 file 
 What do you mean with "whole software"?
You can and should use rsync to send just 1 file, the command syntax is exactly the same. rsync is a drop-in replacement for scp. scp is just objectively worse in every way. 
 Oh ok thanks. I'm happy you spoke up. I thought rsync was just like timeshift for whole disc backup 
 Graphene over Calyx 
 XMPP protocol is almost abandonware. Basic specification is pretty poor, everything what you expect from messenger is a part of some extension. Not supported by particular server or not supported by particular client. Or built on extension still in "draft" past 15 years. Even the most used "pidgin" client is not supporting "must have" basic set of extensions. 
 Have you tried Conversations(Android) or Gajim(desktop)? 
 Tried Gajim 3y ago, put on "something is missing" list. Don't remember exactly.
There is a lot of jabber features not included in basic specification but via XEPs. Did not find a client that has all required XEPs implemented. 
 I cannot agree.

Just try Conversations  on Android and Gajim on desktop.

xmpp is a solid and reliable protocol.  
 1. XMPP is solid. But without XEP is very limited. Client based on pure XMPP is almost unusable for people.
2. Tried to get list of supported XEPs for gajim. https://gajim.org/support/extensions is dead link - bad way to persuade me.
After spending some time of googling, I have got list of supported XEPs. Will give it a chance again. 
 Pidjin is old mate.  See our video for newer ones that all all interconnected 
 Any multiplatform (Linux/Windows) jabber client not still in aloha phase on github? Seeking 3 years already.
(What video do you mean?) 
 Why Gossip>Iris and LibreWolf>Brave?

Also, Session removing PFS is not really a problem at all: https://maglit.me/session-pfs 
 Librewolf has stronger anti finger and isn't pinging Amazon brave at startup.  Reject google chrome changes  
 Many good choices 👏👏👏 
 Why mpv over vlc? Maybe I should make a transition. 
 Higher quality graphics.  Watch something cinematic side by side 
 I can confirm, mpv is much better option. VLC is already purged. 
 dd over any other Backup Solution 
 Why anonaddy over simplelogin? 
 Keet over SimpleX and Signal? Haven’t heard much about Keet lately. 
 Simplex has great forward privacy.
Keet is a different category imo but a great video chat & file sharing tool. (File sharing could use better UI)  
 Why SimpleX over SphinxChat or CipherChat?