You might ask yourself why you would chose sheesy over other tools. The comparisons that follow should be helpful in deciding what's best for you.

Pass

The standard unix pass is a shell script, which requires the presence of various standard unix tools, among which are tree and getopt. The latter are actually not necessarily present, and if they are they may not produce exactly the same results. On OSX for example, the gpg file suffix is shown instead of hidden, and pass goes in an endless loop if getopt is broken, which it is by default when brew reinstall gnu-getopt was not invoked.

sheesy has only one dependency: gpg, and even there it does not depend on the executable, but rather the gpg-agent. It does not invoke the gpg command, and thus will not be confused by a change in the way gpg interprets its arguments between minor version increments.

Besides, as pass just invokes gpg, it suffers from the horrible and hard-to-grok error messages that it produces. Using pass and gpg requires to overcome a significant learning barrier, and you are required to know and understand the 'Web of Trust' and all the error messages that come with not having one big enough to encrypt for the desired recipients.

sheesy is built with great user experience as first class requirement, and even though you will always see the underlying gpg error, it will explain what it means and provide you with hints to solve the issue. When encryption fails, it will list exactly for which recipient you cannot encrypt, and why.

pass even has a few tests, but it's unclear when and where these run. sheesy is developed in a test-driven fashion, and has user-centric tests that model real-world interaction. This is the reason why those interactions are designed to be understandable, consistent and easy to remember.

Gopass

gopass is 'the slightly more awesome standard unix password manager for teams' as claimed on the projects github page. As I have never used it beyond trying it locally, this paragraph might be lacking details. However, a first impression is worth something, and here we go.

As it is a go program, it comes without any dependencies except for the gpg executable. It calls it directly, and thus would be vulnerable to changes to the way gpg parses its arguments.

It's feature-ladden and seems overwhelming at first, it is clearly not centered around user experience. Otherwise the user-journey would be much more streamlined and easier to comprehend. Many advanced features I certainly don't get to enjoy that way.

Somewhat a sybling of the issue above seems to be that it is hell-bent on being a personal password store. Thus it will store meta-data in your home directory and really wants a root-store which is placed in your home by default. So-called 'mounts' are really just a way to let it know about other pass compatible vaults, and I believe that makes it a buzz-word. Nonetheless, this made it hard for me to get started with it, and I still feel highly uncomfortable to use it thanks to it opinionatedness.

Last but not least, and an issue that I find makes the case for not using gopass is that it actually abandons the Web of Trust in favor of simplicity to the user. Even though I understand why one would do that, I think the Web of Trust is an awesome idea, with terrible user experience, which just begs you to make it usable for the masses thanks to better tooling.

Additionally gopass just aims to be a slightly more awesome than pass, which shows as it is basically pass written in go with more features.

Even though it certainly is better than pass, I wouldn't want to use it in its place because it adds so much complexity while entirely removing the 'Web of Trust'. The latter seemed to have happened rather sneakily, which I find problematic.

It should be valued that they actively increase test-coverage, but it also means that they don't do test-driven development, which nourishes my doubt in the quality of the software.