diff --git a/deployment_scripts/deploy_linux.sh b/deployment_scripts/deploy_linux.sh
index 072e14af8..7e9debba2 100755
--- a/deployment_scripts/deploy_linux.sh
+++ b/deployment_scripts/deploy_linux.sh
@@ -139,14 +139,22 @@ fi
 ${python_cmd} get-pip.py
 rm get-pip.py
 
+log_message "Installing pipenv"
+${python_cmd} -m pip install --user -U pipx
+${python_cmd} -m pipx ensurepath
+source ~/.profile
+pipx install pipenv
+
 log_message "Installing island requirements"
-requirements_island="$ISLAND_PATH/requirements.txt"
-${python_cmd} -m pip install -r "${requirements_island}" --user --upgrade || handle_error
+pushd $ISLAND_PATH
+pipenv install --dev
+popd
 
 log_message "Installing monkey requirements"
 sudo apt-get install -y libffi-dev upx libssl-dev libc++1
-requirements_monkey="$INFECTION_MONKEY_DIR/requirements.txt"
-${python_cmd} -m pip install -r "${requirements_monkey}" --user --upgrade || handle_error
+pushd $INFECTION_MONKEY_DIR
+pipenv install --dev
+popd
 
 agents=${3:-true}
 # Download binaries
diff --git a/deployment_scripts/deploy_windows.ps1 b/deployment_scripts/deploy_windows.ps1
index 3438c554b..20f600f51 100644
--- a/deployment_scripts/deploy_windows.ps1
+++ b/deployment_scripts/deploy_windows.ps1
@@ -126,15 +126,19 @@ function Deploy-Windows([String] $monkey_home = (Get-Item -Path ".\").FullName,
         return
     }
 
+    "Installing pipx"
+    pip install --user -U pipx
+    pipx ensurepath
+    pipx install pipenv
+
     "Installing python packages for island"
-    $islandRequirements = Join-Path -Path $monkey_home -ChildPath $MONKEY_ISLAND_DIR | Join-Path -ChildPath "\requirements.txt" -ErrorAction Stop
-    & python -m pip install --user -r $islandRequirements
+    Push-Location -Path (Join-Path -Path $monkey_home -ChildPath $MONKEY_ISLAND_DIR) -ErrorAction Stop
+    pipenv install --dev
+    Pop-Location
     "Installing python packages for monkey"
-    $monkeyRequirements = Join-Path -Path $monkey_home -ChildPath $MONKEY_DIR | Join-Path -ChildPath "\requirements.txt"
-    & python -m pip install --user -r $monkeyRequirements
-    "Installing python packages for ScoutSuite"
-    $scoutsuiteRequirements = Join-Path -Path $monkey_home -ChildPath $SCOUTSUITE_DIR | Join-Path -ChildPath "\requirements.txt"
-    & python -m pip install --user -r $scoutsuiteRequirements
+    Push-Location -Path (Join-Path -Path $monkey_home -ChildPath $MONKEY_DIR) -ErrorAction Stop
+    pipenv install --dev
+    Pop-Location
 
     Configure-precommit($monkey_home)