diff --git a/poetry.lock b/poetry.lock
index e7065cc..afad2e6 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -605,7 +605,7 @@ python-versions = ">=3.7"
 
 [[package]]
 name = "urllib3"
-version = "1.26.14"
+version = "1.26.15"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
 category = "main"
 optional = false
@@ -1020,8 +1020,8 @@ typing-extensions = [
     {file = "typing_extensions-4.5.0.tar.gz", hash = "sha256:5cb5f4a79139d699607b3ef622a1dedafa84e115ab0024e0d9c044a9479ca7cb"},
 ]
 urllib3 = [
-    {file = "urllib3-1.26.14-py2.py3-none-any.whl", hash = "sha256:75edcdc2f7d85b137124a6c3c9fc3933cdeaa12ecb9a6a959f22797a0feca7e1"},
-    {file = "urllib3-1.26.14.tar.gz", hash = "sha256:076907bf8fd355cde77728471316625a4d2f7e713c125f51953bb5b3eecf4f72"},
+    {file = "urllib3-1.26.15-py2.py3-none-any.whl", hash = "sha256:aa751d169e23c7479ce47a0cb0da579e3ede798f994f5816a74e4f4500dcea42"},
+    {file = "urllib3-1.26.15.tar.gz", hash = "sha256:8a388717b9476f934a21484e8c8e61875ab60644d29b9b39e11e4b9dc1c6b305"},
 ]
 watchdog = [
     {file = "watchdog-2.3.1-cp310-cp310-macosx_10_9_universal2.whl", hash = "sha256:d1f1200d4ec53b88bf04ab636f9133cb703eb19768a39351cee649de21a33697"},
diff --git a/site/source/user-manual/connecting/connecting-tor/tor-os/tor-mac.rst b/site/source/user-manual/connecting/connecting-tor/tor-os/tor-mac.rst
index 0f5c552..bcbabaf 100644
--- a/site/source/user-manual/connecting/connecting-tor/tor-os/tor-mac.rst
+++ b/site/source/user-manual/connecting/connecting-tor/tor-os/tor-mac.rst
@@ -38,7 +38,15 @@ Install Tor
 
 .. caution:: If you have the Tor Browser open, close it and quit the application.
 
-#. In the command line, install Tor:
+.. note:: If you are on a very old version of macOS, such as High Sierra (10.13) or below, first execute this command in a Terminal window:
+
+    .. code-block::
+
+        echo 'export PATH="/usr/local/bin:$PATH"' >> ~/.bash_profile
+    
+    Then close the Terminal.
+
+#. Open a new Terminal and install Tor using the following command:
 
     .. code-block::