diff --git a/Makefile b/Makefile
index e433bdb..aeab7c2 100644
--- a/Makefile
+++ b/Makefile
@@ -20,7 +20,29 @@ help:
 	@printf "  make clean         Remove build artifacts\n"
 
 deps:
-	$(PIP) install -e ".[build]"
+	@set -eu; \
+	PIP_CMD="$(PIP)"; \
+	if ! $$PIP_CMD --version >/dev/null 2>&1; then \
+		if command -v pip3 >/dev/null 2>&1; then \
+			PIP_CMD="pip3"; \
+		elif $(PYTHON) -m ensurepip --version >/dev/null 2>&1; then \
+			$(PYTHON) -m ensurepip --upgrade; \
+		elif command -v apt-get >/dev/null 2>&1; then \
+			echo "pip missing; installing python3-pip via apt-get (sudo required)"; \
+			sudo apt-get update; \
+			sudo apt-get install -y python3-pip; \
+		elif command -v dnf >/dev/null 2>&1; then \
+			echo "pip missing; installing python3-pip via dnf (sudo required)"; \
+			sudo dnf install -y python3-pip; \
+		elif command -v brew >/dev/null 2>&1; then \
+			echo "pip missing; installing python via Homebrew"; \
+			brew install python; \
+		else \
+			echo "Unable to bootstrap pip automatically. Install pip for $(PYTHON) and rerun make deps."; \
+			exit 1; \
+		fi; \
+	fi; \
+	$$PIP_CMD install -e ".[build]"
 
 build: deps
 	$(PYTHON) -m PyInstaller --noconfirm --clean --onefile --name flow --paths "$(SRC_DIR)" "$(ENTRYPOINT)"