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It's a deep rabbit hole but here are a few ideas for you 📝

You'll want to have up to date hardware and software, because vulnerabilities will become known and this means it is possible to access your system. Maybe think of it as having a healthy diet for your tech, so it has a strong immune system 🥕

A VPN can help, but you should know that the company behind it can theoretically still see what connections you are opening and analyze Metadata. However, your ISP will have a lot less to work with. They won't see that you are connecting to a trans related server, but only a single connection to your VPN. Just ensure you trust the company and consider the jurisdiction it is in ⚖️

If you want to go the extra mile you might want it give Tails OS a spin. It's free and can run from a DVD or USB drive, and won't leave a trace when switched off. It runs the tor browser out of the box 📀

Don't try to disappear and hide everywhere, this is very noticeable. You'll want to create secondary accounts for your trans related activities. For example you could remember the logins and only use it on Tails, but you would still have your every day stuff like maybe Instagram, so all appears normal 😇

The next step would be to have privacy focused hardware. For example System 76 will disable the IME (Intel Management Engine), which is built in to every Intel CPU and provides a massive vulnerability 💻

As far as I am aware this also applies to phones with a SIM. The sim is like a little computer on its own, just like the chip on your bank card. It has memory and a processor and it runs a special version of Java. It has full access to the hardware and can be trivially patched from the cell network. Personally I have not investigated how to circumvent this, but just be aware that this is a major vulnerability of most phones 💳

Keep in mind that using ANY closed source software is going to pose a beefy vulnerability. Be that Windows or an Nvidia driver. It simply can't be audited for vulnerabilities, which might be left in on purpose. Furthermore, if you are checked by authorities and they take your phone or laptop, you have to assume it is compromised. Many corps will simply get rid of hardware when this happens 🤷🏻‍♀️

It's better not to store sensitive data locally, but rather in an encrypted form online. Encrypted data can attract attention if it is found, such as a harddrive, thumbdrive or dvd. Same considerations as with the VPN company. Think of it as e2ee (end to end encryption, such as matrix and signal), but for your data when it is stored and not actively being used. You can search online how to do this. All in all it is probably best to simply not store any data at all by yourself, and stick to trusted online services only 😌

A little on the internet. Let's say you are royally screwed and the internet is switched off or you are blocked from accessing it entirely. At this point you'll want to understand how to make your own network, perhaps with some gateways that are still connected to the internet. This is a large topic which ranges from HAM radio to satallite connections. There is also a risk in being detected. Just know that there is software that can leverage everyday tech in your hardware such as Bluetooth and Wi-Fi to create a grassroots mesh network. In Berlin there is one day a year where such a network is set up just for fun, and it's good training, so maybe give it a try in your local community 📻

Twice I've mentioned using companies, for a vpn or for storing data. But you should know that it is quite common for people to host all sorts of services on their own from home, just like many instances on Lemmy. You can assign someone in your local community to be responsible for this. It can be entirely local and part of your mesh network, so it does not rely on the internet. Or it could be in another country. Just know that it's possible and it's flexible 🏡

As you can see, there is endless stuff to keep in mind, and you will always be taking risks. It's a full time job for many people. I am certain I forgot something. And I haven't even mentioned the social aspect, for example how to handle strangers. But as long as we remain connected and have a few people who invest effort into this, we can stay reasonably safe, even if your area turns into Uganda 🫣

And lastly, keep in mind that all good people are friends and you are not alone ❤️