diff --git a/CHANGELOG.md b/CHANGELOG.md
index dc45674..b777a91 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,13 @@ The format is based on [Keep a Changelog][1], and this project adheres to
 
 ## [Unreleased]
 
+### Added
+
+- Add `--openssl-path` option when initializing transcrypt to use a specific
+  openssl version instead of the default version found in `$PATH`. This will be
+  most useful to macOS users who might want to use a newer version of OpenSSL
+  than the one that comes included.
+
 ### Fixed
 
 - Respect Git `core.hooksPath` setting when installing the pre-commit hook. (#104)
diff --git a/README.md b/README.md
index 6f2623b..0c73598 100644
--- a/README.md
+++ b/README.md
@@ -201,6 +201,11 @@ directory.
              the password to derive the key from;
              defaults to 30 random base64 characters
 
+      --openssl-path=PATH_TO_OPENSSL
+             use OpenSSL at this path; defaults to 'openssl' in $PATH.
+             To change after initialization:
+                 git config transcrypt.openssl-path NEW_PATH
+
       -y, --yes
              assume yes and accept defaults for non-specified options
 
diff --git a/man/transcrypt.1.ronn b/man/transcrypt.1.ronn
index d9c3df0..50d9757 100644
--- a/man/transcrypt.1.ronn
+++ b/man/transcrypt.1.ronn
@@ -25,6 +25,11 @@ The transcrypt source code and full documentation may be downloaded from
     the password to derive the key from;
     defaults to 30 random base64 characters
 
+  * `--openssl-path`=<path_to_openssl>:
+    use OpenSSL at this path; defaults to 'openssl' in $PATH.
+    To change after initialization:
+        git config transcrypt.openssl-path NEW_PATH
+
   * `-y`, `--yes`:
     assume yes and accept defaults for non-specified options