Initially, setting up Vyper (an experimental language, with python-like syntax, for writing smart contracts on ethereum) seemed as simple as following the instructions.

it wasn't.

If you like to skip the details/troubleshooting, head over to TL;DR

pyenv

I've written about why I prefer pyenv earlier

I'm not sure whether my “misfortune” was due to pyenv, but it could be.

To top it off, I also used virtualenv as suggested in the official docs. (I would have done that any way)

So it added to complications, and “simple” instructions did not work.

I had discussion on gitter about this issue, and one person had also faced problems. (But he wasn't using virtualenv)

Problems and Solutions

It seemed that missing requirements.txt is the problem (and the in-progress documentation) Several dependencies are not clearly listed.

First I ran into the following error, but the solution is well documented.

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build/temp.macosx-10.12-x86_64-3.6/_openssl.c:493:10: fatal error: 'openssl/opensslv.h' file not found

So I had to set the CFLAGS and LDFLAGS variable, as mentioned on the official instructions page.

While troubleshooting, I realized that dependencies are badly broken.

I manually installed py-evm because it is listed in setup.py

This installed a whole lot of packages correctly which are required later.

e.g. This troubleshooting guide, asks to install a specific version of pypandoc.

When I did that, I saw several errors of the nature packageA requires pakcageB, which is not installed. Yet, at the end I saw Successfully installed pypandoc-1.4

That does not make sense.

pip install py-evm I think installed whole lot of those missing packages correctly.

(Note: In my latest attempt to verify these instructions, make worked after this)

Then I ran into error related to pytest-runner

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distutils.errors.DistutilsError: Download error for https://files.pythonhosted.org/packages/9e/b7/fe6e8f87f9a756fd06722216f1b6698ccba4d269eac6329d9f0c441d0f93/pytest-runner-4.2.tar.gz#sha256=d23f117be39919f00dd91bffeb4f15e031ec797501b717a245e377aee0f577be: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:748)

Essentially it was trying to download pytest-runner, so first I tried curl using that URL (minus #sha256..) it worked. It dumped binary on the console. So there was no error reaching and downloading the file. So I manually pip install pytest-runner==4.2 After which make worked. (make test still failing, because I'm getting same error, but for ethereum)

I think it may have been “one off” error, cause in later attempts, I did not face this issue.

TL;DR : Steps that worked

As mentioned in the [official documentation] (http://viper.readthedocs.io/en/latest/installing-vyper.html#macos) I already had python 3.6 and gmp installed via brew

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pyenv virtualenv 3.6.2 py362vyper
pip install --upgrade pip
export CFLAGS="-I$(brew --prefix openssl)/include"
export LDFLAGS="-L$(brew --prefix openssl)/lib"
pip install scrypt
pip install py-evm==0.2.0a12
pip install pytest-runner==4.2
git clone https://github.com/ethereum/vyper.git
cd vyper
make
pip install ethereum==2.3.1
pip install pytest-cov==2.5.1
make test
vyper examples/crowdfund.v.py

Note : In the steps above, I've listed a specific versions of various packages I installed manually. Eventually, It was not required. So try without mentioning specific version at first. If that does not lead to success, maybe try specific version - which may differ depending on when you are reading this