diff --git a/tools/ssh_helpers/Usage.md b/tools/ssh_helpers/Usage.md
index 967ca9c1e3..0804ecf7a3 100644
--- a/tools/ssh_helpers/Usage.md
+++ b/tools/ssh_helpers/Usage.md
@@ -1,4 +1,29 @@
+# Prerequisites
+
+These scripts make it easy to connect to running Habitat instances. To use them, you'll need to set up a few things first:
+
+* Make sure you've downloaded the `habitat-srv-admin` key and placed it at at `~/.ssh/`.
+* If you haven't already, create an IAM user for yourself in Habitat AWS. You'll need membership in the `admins` group and programmatic access. Note your generated access key ID and secret.
+* Install [the AWS CLI](https://docs.aws.amazon.com/cli/latest/userguide/cli-install-macos.html) and place it on your PATH.
+* Configure the AWS CLI using your Habitat AWS IAM credentials.
+* Install [jq](https://stedolan.github.io/jq/). (e.g., `brew install jq`)
+* Install [tmux](https://github.com/tmux/tmux/wiki). (e.g., `brew install tmux`)
+* Install [tmuxinator](https://github.com/tmuxinator/tmuxinator). (`gem install tmuxinator`)
+
+# Generating and Updating Configuration
+
+Once you're set up with the prerequisites listed above, you should be able to generate SSH and tmuxinator configurations using the following commands (executed from within this directory):
+
 ```
-update-habitat-ssh acceptance
-hab-env acceptance
+./update-habitat-ssh acceptance
+./update-habitat-ssh live
 ```
+
+And with that, connect to running environments:
+
+```
+./hab-env acceptance
+./hab-env live
+```
+
+Any troubles, ask in #core-dev! Enjoy.
diff --git a/tools/ssh_helpers/hab-env b/tools/ssh_helpers/hab-env
index bffa1e6038..4a8a7de8c5 100755
--- a/tools/ssh_helpers/hab-env
+++ b/tools/ssh_helpers/hab-env
@@ -9,7 +9,7 @@ SESSION="hab_${HAB_ENV}"
 
 # (Re-)generate a tmuxinator session description. This ensures we're
 # always up-to-date
-~/bin/generate-habitat-env-tmuxinator.sh ${HAB_ENV} \
+./generate-habitat-env-tmuxinator.sh ${HAB_ENV} \
     > ~/.tmuxinator/${SESSION}.yml
 
 # TODO: What if the session is already running?