Moving from 1Password to KeePass | #macos | #macsecurity


I’ve been using password managers for a long time, starting with the open-source KeePass in Windows nearly 20 years ago. When I moved back to the Apple world in the late 2000s, I was drawn in by the shininess of 1Password. It was made just for the Mac and looked the part. KeePass was always rough around the edges, while 1Password neatly integrated with the Mac and iPhone. (For evidence of my longtime 1Password loyalty, see “1Password 7 for Mac Offers a Fresh Look… for an Upgrade Price,” 18 June 2018.)

However, I always somewhat regretted switching away from KeePass, which stores its encrypted database in a standardized, open format. The original KeePass has always been Windows-only, but there are multiple KeePass-compatible apps for all platforms and you’re free to pick whichever one is right for you. With KeePass, I always felt like I had complete control of my password database. I was somewhat uncomfortable with 1Password’s proprietary database format, and later with how AgileBits pushed 1Password users to store passwords on 1Password.com, but I felt the tradeoff for less friction was worthwhile.

Unfortunately, 1Password developer AgileBits seems to be moving away from its Apple-centric roots. The upcoming 1Password 8, currently in early access, shifts the password manager to the cross-platform Electron development framework. In essence, Electron packages a Web app in such a way that it acts like a native Mac app, which is great for cross-platform compatibility but seldom results in an app that feels like it was designed for the Mac. Electron is widely criticized, and deservedly so, but there are many apps that might not have been ported to the Mac without it.

The other notable change is that 1Password 8 will no longer let you store your password database locally. Instead, you have to use 1Password.com, which some people are not comfortable with. I have successfully used 1Password.com for a few years now (the company gave me a free subscription) but would prefer to have my password database under my direct control.

Along with my philosophical dislike of having my essential data locked into a single provider, I’ve also been running into more annoyances with 1Password. For example, the 1Password browser extension used the Command-\ shortcut to autofill passwords—but recently the extension has changed to Command-Shift-X to be consistent across all platforms. That’s just one small example of AgileBits changing something on the Mac to promote cross-platform compatibility. Overall, both the desktop and mobile apps have gotten clunkier and slower. Even my non-technical wife, to whom I introduced to 1Password years ago, made a comment about how it wasn’t as smooth as it used to be.

I still think 1Password is a great product, and you are far, far better off with any password manager than none at all. But I decided some time ago to switch from 1Password back to KeePass. It’s less about being unhappy with 1Password’s direction than preferring my data in open formats, and AgileBits’ recent changes have made me decide that the tradeoff between convenience and openness was no longer worth it.

I also wanted more local control over my data. Recent iCloud outages have made me much leerier of relying on the cloud. I recently purchased a Synology NAS and several hard drives to store more of my data locally. I’ll write about that experience soon, but for now I mention it only because that’s where I’m now storing my passwords.

So if you’re fed up with proprietary, cloud-based password managers, read on! But understand that going your own way, while empowering, isn’t as easy or necessarily as secure. There’s been a lot of talk lately about “sovereignty” in regards to software. Specifically, ownership and control of your own data, free of big tech’s cloud. But tech companies like Apple and Google are big for a reason: control comes with a cost. As Spider-Man says, “With great power comes great responsibility.”

If you want total control over your data and have the time and skills to securely maintain it, KeePass may be a good option for you. If what I describe below sounds like too much trouble but you still want an open-source solution, check out Bitwarden, which offers both a cloud service and a self-hosted option (though the self-hosted option is a total pain to set up). I tried it but had trouble importing my 1Password vault.

Understanding the Tradeoffs of KeePass

The big selling point of cloud-based password managers like 1Password and LastPass is convenience. You don’t have to worry about securing, syncing, and backing up your password database, and there’s nothing wrong with making that choice. There’s far less risk of data loss than if you’re doing it yourself, syncing setup and maintenance is far easier, and you don’t have the headaches of system administration and security maintenance.

With KeePass, there is no cloud service. You are given an encrypted database in the open KDBX format, and you choose where to store it. That could be on your Mac, on a NAS, or in a cloud service like Dropbox, Google Drive, or iCloud. You can sync your password database directly between a Mac and your mobile devices, but it would be a hassle. A NAS or a cloud service helps you fluidly sync your passwords between platforms and devices. It’s also your responsibility to back up that file and maintain revisions in case you screw something up.

Because of this open approach, you can choose from many KeePass-compatible apps to choose from, across multiple platforms. I’ve recently used:

For many, choosing an app can be overwhelming, but I enjoy being able to try different approaches. And I’ve had no trouble sharing my KeePass database among multiple apps.

Whatever app you choose, be certain that you trust the developer completely—it’s not inconceivable that a malicious app could masquerade as a KeePass-compatible app and be silently stealing your passwords in the background. There has been at least one instance of a site modifying the KeePass code for Windows and injecting adware, though I’m not aware of passwords ever being compromised. (This is part of the tradeoff between open and closed platforms. See “Apple’s App Store Stubbornness May Be iOS’s Greatest Security Vulnerability,” 8 April 2022.)

Transferring from 1Password to KeePass

It took me a while to figure out how to switch from 1Password to KeePass. In addition to my passwords, I also maintain my two-factor authentication TOTP codes in 1Password and I was unsure of how KeePass would handle them. Thankfully, none of this turned out to be a problem.

The developer of the iOS KeePassium app has written excellent documentation for making the switch, explaining how to export your 1Password vault locally and then import it into KeePassXC on the desktop. (KeePassium is not available on the Mac.) The main limitation is that 1Password doesn’t export attachments, so you’ll have to add them back to the corresponding KeePassXC entries manually. The KeePassium method looks long, but it only took me a few minutes to complete, and that’s how I made the switch.

If you want a KeePass solution that is more coherent between Mac and iOS, Strongbox offers apps for both macOS and iOS. Its transfer process is simpler than KeePassium’s, but there is a major omission in Strongbox’s instructions: you can’t export an online database from 1Password, so you must first follow KeePassium’s instructions for transferring your 1Password database to a local vault, after which you can export from the local vault.

I tried both methods, and both worked well, with all of my TOTP codes intact. Strongbox’s import actually worked a little better, since it preserved my favorite entries. However, I had already moved my 1Password vault to KeePass and had made some changes, so it wasn’t worth going through all of that again. I’m also not currently using Strongbox on the Mac for reasons I’ll explain below.

Syncing KeePass Between Devices

It’s easy enough to export from 1Password on your Mac, but how do you get that database onto your iPhone and other devices, and keep that database in sync between them? The easy answer is to use a cloud service, and that’s what most people do. But I explicitly wanted to store my passwords on my own hardware on my local network.

Apple now relies on SMB as the standard file-sharing protocol for macOS, and you can even access SMB servers from the iOS Files app. Unfortunately, you cannot access your password database file from an SMB server via the Files app when you’re not connected to the server—there’s no offline caching—which renders it useless when you’re not on your local network. I have a VPN connection to my Synology so I can use it remotely, but I don’t want to have to activate the VPN just to access my passwords when I’m away from home.

I also tried Synology Drive, which is similar to Dropbox and Google Drive but hosted on your own Synology NAS. Synology Drive provides two apps for iOS, and both integrate with the Files app, but unfortunately using them for syncing KeePass-compatible iOS apps is problematic.

I found the most reliable local syncing method to be an old-fashioned WebDAV server (you may remember WebDAV from the days of Apple’s iDrive). Thankfully, Synology makes it easy to set up a WebDAV server in a few clicks. The iOS Strongbox app can connect to WebDAV servers without relying on a third-party app, so that’s what I’m using on my iPhone, and it’s doing a great job of staying in sync without additional complications. I’ve even made changes to my database on Strongbox while away from the house and seen it sync when I get home. When I eventually switch my wife over from 1Password, I’ll set her up with Strongbox.

My Preferred KeePass-Compatible Apps

I’ve settled on KeePassXC for the Mac and Strongbox for the iPhone. Both apps are open source. The beauty of KeePass is I can mix and match apps how I see fit.

I use Strongbox on the iPhone because of its built-in WebDAV support, but it’s a powerful app in its own right. It supports autofill, Face ID, security audits, password generation, and all of the modern amenities you expect in a password app.

Strongbox for iPhone

Strongbox has some neat tricks of its own. In addition to Face ID, you can also set a secondary PIN for authentication. Additionally, you can set a “duress PIN,” which is a secondary PIN you would enter if someone were trying to force you to let them access your passwords. You can set the duress PIN to display a dummy password database, a phony error, or even wipe the local copy of your database.

Strongbox's duress PIN

You can even change the app icon to disguise Strongbox as another kind of app, like a calculator. I’m not sure how effective that would be, given that it’s still called Strongbox, but I appreciate the novelty.

Strongbox's app icon disguised as a calculator app

The best features of Strongbox require a subscription of about $15 per year, but I’m more than happy to support this high-quality open source app.

Strongbox for macOS also boasts a well-designed interface that feels Mac-native. It compares favorably to 1Password or any other proprietary password manager. It’s also distributed exclusively via the Mac App Store, so you get Apple’s stamp of approval. Unfortunately, as elegant as Strongbox’s macOS-native desktop version is, it doesn’t include Web browser extensions. Instead, Strongbox recommends the Mac’s built-in autofill function, but that works only in Safari, not in Brave, my browser of choice.Strongbox for the Mac There are several possible workarounds for this. For instance, you could use one of the available standalone KeePass-compatible extensions for Google Chrome and other browsers. My current desktop solution is KeePassXC, which isn’t pretty or particularly Mac-like but does provide browser extensions. It’s also incredibly fast and lightweight. I have some criticisms but bear in mind that KeePassXC is totally free and maintained by volunteers.KeePassXC

I never considered 1Password 7 to be sluggish until I experienced KeePassXC’s speed. On the downside, KeePassXC lacks features that are commonplace in other password managers. Notably, it has no security audit feature like 1Password, nor any way to denote a login as a favorite except by storing entries in a manually created folder.

The KeePassXC browser extension works well, but it’s not as well-integrated as 1Password’s. After you install the browser extension, you must enable it for each browser you want to use. At first, I couldn’t get it to work with just Brave selected, but after I also selected Chrome and Chromium (which Brave is based on), it worked. You also have to click an authorization prompt to allow autofill on each site, which makes sense from a security standpoint but is annoying. Plus, you must select an option for websites that require you to enter your username and password on separate pages, though there’s usually an in-browser prompt for that.

As necessary as browser integration is, the KeePassXC browser extension is far from perfect. It relies on a connection to the KeePassXC desktop app, and sometimes that connection gets interrupted until I refresh it. (In my experience, this problem can crop up with any extension that has to connect to a local app instead of a cloud service. I’ve had similar issues with 1Password.)KeePassXC extension error

Most of the time it works just fine, and it fulfills what I really need in a password manager browser extension: noticing when I add a new password or change a password and offering to update the database.

Data Sovereignty Isn’t for Everyone

If all this sounds like I left a smooth and perfectly functional app for a hodgepodge of cobbled-together solutions, it’s because I did. But now that I’ve hashed out the kinks, it works pretty well. I’ve created and changed several passwords on both my Mac and iPhone since switching from 1Password, and I have experienced no data corruption or loss.

The upside of doing all of this is that I now have total control over my password database. It’s stored in Synology Drive, which keeps revisions and syncs a local copy to my Mac, where Time Machine also stores revisions. Plus, my Synology NAS backs up remotely to IDrive (unrelated to Apple’s old cloud storage offering) and locally to a 14 TB external drive, and they also keep revisions, so my password database is well secured.

It was some trouble to set up, but for me, it was worth it to gain sovereignty over my password database. It’s now held right here in my home, with multiple encrypted backups both here and off-site. I don’t have to worry about a cloud service being taken offline or going out of business.

So, if you’re unhappy with 1Password’s direction and want more control over your data, check out KeePass and its open-source brethren.



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