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Privacy Tool Recommendations Should Come with Caveats

03 Jun, 2026

This post was last edited 0 minutes ago .

A few years ago, my enthusiastic recommendation of Tuta Mail to a friend new to privacy tools backfired. He struggled with the user interface, found the constant updates annoying and was not happy with Tuta's limited search capabilities. He dropped Tuta and transferred to Outlook. I interviewed him about his reasons in Why my Friend Quit Tuta Mail.

While I chat to my friend on Signal, I imagine he'll think twice about adopting any new privacy tools on my advice. Looking back on this, I should have

advised my friend about Tuta

explained why Tuta has superior privacy and security

warned him about potential frustrations and pitfalls

It's this third part I want to highlight today. We can advocate for privacy and realistic at the same time; evangelism can backfire , and it's a simple truth that many small frustrations in my digital workflow are a direct result of my decision to use privacy tools. It doesn't hurt to warn others when we advise them to switch.

I'll use the steelman approach I used in Privacy Tools Are Not Worth the Hassle and not pull punches in describing these issues.

Here they are:

Encryption makes things difficult<br>Just last week, Tuta published their blog article Easier inbox rules, Faster Sync, & Search! (+More). While this is good news—I still need to test these improvements—it's worth noting that I've been dealing with Tuta Mail's frustratingly difficult and slow search function for nearly 8 years now.

Enabling the search for your mailbox consumes memory on your device and might consume additional traffic.

(warning on Tuta Mail when you initiate a search)

Up until now, doing a search on the desktop application involved setting the date parameters for your search, reading the warning above and waiting a long time. I was told that encryption makes seemingly simple things, like searching all your mails, hard.

Managing your own encryption keys is scary<br>When setting up an encrypted service like Ente Photos or Standard Notes, you are responsible for storing your password. If you lose it, you lose your photos, your notes. It can be hard to get that point across today, where everyone is used to recovery options for lost passwords.

Compartmentalisation can be tedious<br>I used Firefox's container option when browsing. I like the idea but it's an extra step when logging in (I get asked how I want to open the site). I also get the feeling that if I log in after I've engaged with a given website, I usually have to start over once logged in via the Firefox container.

I use different devices for work, and different users on devices for different purposes. To get to my work email, I have to start up a dedicated laptop or reboot into another operating system on this PC.

On GrapheneOS, when I want to check my bank account, I have to switch to my Google environment user. Sending information between different users can be difficult too. I'll take a screenshot in one GrapheneOS user and have to then upload that to my Nextcloud server in order to access it on my main user. There are solutions for this, but they have not worked for me.

Using a password manager and 2FA introduces annoying extra steps<br>I use KeePass for everything. I also close apps, like browsers, when I'm done with them, and I like to turn my PC off at night sometimes to give myself a break from my digital life. As a result, I have to open my KeePass data base regularly, type in the master password, find the relevant entry and execute an auto-fill with a keyboard shortcut (which sometimes 'misfires') whenever I want to do anything account related. I save passwords in desktop apps but don't like to do this in my browser.

For two-factor authentication I use he open source phone app Aegis Authenticator. Using 2FA when logging in to important services is essential for security, but it is an annoying to have to find my smartphone, type in the Aegis password and copy the temporary number in order to access a website. I worry that these little 2FA tasks will accumulate over time.

Alternative search tools can be puzzling<br>My last article was an interview with Bruno, the software engineer of Uruky, a privacy search engine that you have to pay for. I'm a fan of Uruky and have started paying for it, but have also been honest with Bruno about my frustrations.

If you leave the Settings as the default, then you end up with quite unexpected search results, as Uruky puts the most privacy-focused Web Search Providers at the top. Only when I reordered the search providers did I get expected results. I also had to jump through a few hoops in order to not have to add my account number each time I started my browser, something Bruno helped me with. Lastly, image search was non-existent when I started, though it's in beta now.

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