diff --git a/homebrew/Brewfile b/homebrew/Brewfile
index 2e0af1e..1f43fff 100644
--- a/homebrew/Brewfile
+++ b/homebrew/Brewfile
@@ -22,8 +22,8 @@ brew "prettyping"           # Better ping
 brew "httpie"               # Better curl
 brew "nushell"              # Data manipulation shell
 brew "shellcheck"           # Lint for bash
-brew "pyenv"                # Python installations
-brew "pyenv-virtualenv"     # Python virtualenvs
+brew "python"               # Latest version of Python
+brew "poetry"               # Project-based Python dependencies
 brew "ruby"                 # Newer than default ruby
 brew "ansible"              # Deploy to local server
 brew "terraform"            # Deploy cloud infra
@@ -43,6 +43,9 @@ brew "nmasur/repo/update-ssh-config"  # Update .ssh/config
 # Experimental
 tap "cjbassi/ytop"          # Fancy system performance
 brew "cjbassi/ytop/ytop"
+brew "haskell-stack"        # Latest version of Haskell
+brew "noti"                 # Create system notifications
+brew "kakoune"              # Modal editor
 
 # Not Installed
 # pulumi
diff --git a/homebrew/Caskfile b/homebrew/Caskfile
index 08f7f5f..221274d 100644
--- a/homebrew/Caskfile
+++ b/homebrew/Caskfile
@@ -1,35 +1,39 @@
 tap "homebrew/cask"
 
 # Core Applications
-cask "alacritty"
-cask "google-chrome"
-cask "slack"
-cask "zoomus"
-cask "1password"
-cask "1password-cli"
-cask "lastpass"
-cask "dropbox"
+cask "alacritty"            # My terminal
+cask "firefox"              # My browser
+cask "slack"                # Work chat
+cask "zoomus"               # Video conference
+cask "1password"            # Work pwm
+cask "1password-cli"        # Pwm for tmux
+cask "dropbox"              # File sharing
+cask "docker"               # Containers
+
+# Helpful Applications
+cask "obsidian"             # Notes
+cask "github-desktop"       # Git GUI
+cask "google-chrome"        # Alt browser
+cask "postman"              # API testing
+cask "drawio"               # Diagrams
+
+# Auxiliary Tools
+cask "scroll-reverser"      # Mouse vs. trackpad
+cask "meetingbar"           # Scheduling
+cask "gitify"               # GitHub notifications
 
 # Fonts
 tap "homebrew/cask-fonts"
 cask "font-fira-mono-for-powerline"
 
-# Auxiliary Tools
-cask "docker"
-cask "github-desktop"
-cask "keybase"
-cask "scroll-reverser"
-cask "authy"
-cask "postman"
-cask "drawio"
-cask "meetingbar"
-
 # Personal
-cask "discord"
-cask "steam"
-cask "vlc"
-cask "calibre"
-cask "firefox"
+cask "lastpass"             # My pwm
+cask "authy"                # Authentication
+cask "keybase"              # Encryption
+cask "discord"              # My chat
+cask "steam"                # Games
+cask "vlc"                  # Video player
+cask "calibre"              # Ebook manager
 
 # Don't bother
 # cask "skype"