Software⏱️ 3 min read📅 2026-06-15

How to Fix: Python (pyenv) Compile error - missing OpenSSL on mac os x

Fixing Python compile errors with missing OpenSSL on macOS Mojave.

Quick Answer: Install the correct version of OpenSSL and ensure pkg-config is installed to resolve the issue.

📋 Table of Contents

  1. ⚠️ Common Causes
  2. 🚀 How to Resolve This Issue
  3. ✨ Wrapping Up

Python (pyenv) Compile error - missing OpenSSL on mac os x: This issue affects users trying to install AWS EB-CLI on macOS Mojave 10.14 and encountering an error when compiling Python.

This error can be frustrating, especially for those migrating from Windows to Mac. However, with the right steps, you can resolve this issue and successfully install AWS EB-CLI.

⚠️ Common Causes

  • The primary reason for this error is that LibreSSL 2.6.4 and earlier versions do not provide the necessary APIs required by Python. This is due to a compatibility issue between LibreSSL and Python.
  • An alternative cause could be related to the installation of additional SDK headers or the version of OpenSSL being used.

🚀 How to Resolve This Issue

Installing OpenSSL using Homebrew

  1. Step 1: Install OpenSSL via Homebrew by running the command 'brew install openssl' in your terminal.
  2. Step 2: Once installed, you may need to link the OpenSSL library to the correct location. Run 'brew link openssl --force' to do so.

Installing additional SDK headers and checking OpenSSL version

  1. Step 1: Install additional SDK headers by running 'sudo xcode-select --install' in your terminal.
  2. Step 2: Check the version of OpenSSL installed on your system. If it's compatible with Python, you can proceed to install AWS EB-CLI.

✨ Wrapping Up

To resolve this issue, first ensure that you have installed OpenSSL using Homebrew and linked the library correctly. Alternatively, check if additional SDK headers are required and verify the version of OpenSSL being used. By following these steps, you should be able to successfully compile Python and install AWS EB-CLI on your Mac.

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