diff --git a/nix/better-prompt.nix b/nix/better-prompt.nix
new file mode 100644
--- /dev/null
+++ b/nix/better-prompt.nix
@@ -0,0 +1,31 @@
+{ lib
+, stdenv
+, powerline
+, powerline-fonts
+, shellcheck
+, writeTextFile
+, runtimeShell
+}:
+
+# Normally we would want to use writeShellApplications for scripts, however,
+# since file will be sourced, we do not want to inherit 'set -euo pipefail'
+# as this will cause the development shell to exit for any failed command
+writeTextFile rec {
+  name = "better-prompt";
+  destination = "/bin/${name}";
+  text = ''
+    #!${runtimeShell}
+
+    PATH=${powerline}/bin:$PATH
+    powerline_fonts=${powerline-fonts}
+    powerline_root=${powerline}
+
+    source ${./start-powerline.sh}
+  '';
+
+  checkPhase = ''
+    ${stdenv.shellDryRun} $target
+    # Need to pass -x so that shellcheck will source external files
+    ${shellcheck}/bin/shellcheck -x $target
+  '';
+}
diff --git a/nix/dev-shell.nix b/nix/dev-shell.nix
--- a/nix/dev-shell.nix
+++ b/nix/dev-shell.nix
@@ -4,6 +4,7 @@
 , amqp-cpp
 , arcanist
 , aws-sdk-cpp
+, better-prompt
 , boost
 , cargo
 , cmake
@@ -105,6 +106,9 @@
       export ANDROID_SDK_ROOT=''${ANDROID_SDK_ROOT:-$HOME/Library/Android/sdk}
     fi
 
+    # Provide decent bash prompt
+    source "${better-prompt}/bin/better-prompt"
+
     echo "Welcome to Comm dev environment! :)"
   '';
 }
diff --git a/nix/overlay.nix b/nix/overlay.nix
--- a/nix/overlay.nix
+++ b/nix/overlay.nix
@@ -41,6 +41,8 @@
 
   arcanist = prev.callPackage ./arcanist.nix { };
 
+  better-prompt = prev.callPackage ./better-prompt.nix { };
+
   protobuf_3_15_cmake = prev.callPackage ./protobuf_3_15.nix { };
 
   devShell = final.callPackage ./dev-shell.nix { };
diff --git a/nix/start-powerline.sh b/nix/start-powerline.sh
new file mode 100644
--- /dev/null
+++ b/nix/start-powerline.sh
@@ -0,0 +1,70 @@
+#!/usr/bin/env bash
+
+# Check if shell is using a default BSD or GNU prompt
+if [[ ${PS1} != '\s-\v\$'* ]] && \
+    [[ ${PS1} != '%n@%m %1~ %#'* ]]; then
+  # User already has an opinionated PS1, just leave
+  return 0
+fi
+
+if test "$(uname)" = "Darwin" ; then
+  COMM_CACHE="${XDG_CACHE_HOME:-$HOME/Library/Caches}/app.comm"
+else
+  COMM_CACHE="${XDG_CACHE_HOME:-$HOME/.cache}/comm"
+fi
+
+COMM_EMITTED_WARNING="$COMM_CACHE/powerline_warning"
+# Only emit this the first time, as it's suprising to the user for the prompt
+# to be replaced, but avoid emitting the warning on subsequent invocations
+if [[ ! -f "$COMM_EMITTED_WARNING" ]]; then
+  echo "Default prompt found, attempting to enable powerline" >&2
+
+  # Create file to ensure it exists for next time this is run
+  mkdir -p "$COMM_CACHE"
+  touch "$COMM_EMITTED_WARNING"
+fi
+
+# Check if the powerline fonts are installed
+# If the font is missing then many of the glyphs will render as ?
+# Adapted from https://github.com/powerline/fonts/blob/master/install.sh
+if test "$(uname)" = "Darwin" ; then
+  # MacOS
+  font_dir="$HOME/Library/Fonts"
+else
+  # Linux
+  font_dir="${XDG_DATA_HOME:-$HOME/.local/share}/fonts"
+  mkdir -p "$font_dir"
+fi
+
+if [[ ! -f "$font_dir/Droid Sans Mono for Powerline.otf" ]]; then
+  if [[ ! -d "${powerline_fonts:-/doesnt-exist}" ]]; then
+    echo "Unable to determine powerline fonts location" >&2
+    return 1
+  fi
+
+  echo "Installing powerline fonts" >&2
+  find "$powerline_fonts" \
+    \( -name "*.[ot]tf" -or -name "*.pcf.gz" \) -type f -print0 \
+    | xargs -0 -n1 -I % cp "%" "$font_dir/"
+
+  if test "$(uname)" = "Darwin" ; then
+
+    if [[ "$TERM_PROGRAM" == "Apple_Terminal" ]]; then
+      echo "For glyph support, please:
+  Select Terminal > Preferences > Text > Font > Change > \
+Select font with 'for Powerline' in the name" >&2
+    elif [[ "$TERM_PROGRAM" == "iTerm.app" ]]; then
+      echo "For glyph support, please:
+  Select iTerm2 > Preferences > Profiles > Text > Font > \
+Select font with 'for Powerline' in the name" >&2
+    fi
+
+  elif which fc-cache >/dev/null 2>&1 ; then
+      # Reset font cache on Linux
+      echo "Resetting font cache, this may take a moment..." >&2
+      fc-cache -f "$font_dir"
+  fi
+fi
+
+# shellcheck source=/dev/null
+source "${powerline_root:-.}/share/bash/powerline.sh"