diff --git a/Makefile b/Makefile
index 56fc493d358a7..51e1b6a707371 100644
--- a/Makefile
+++ b/Makefile
@@ -60,8 +60,9 @@ coderd/database/dump.sql: $(wildcard coderd/database/migrations/*.sql)
 coderd/database/querier.go: coderd/database/dump.sql $(wildcard coderd/database/queries/*.sql)
 	coderd/database/generate.sh
 
+# This target is deprecated, as GNU make has issues passing signals to subprocesses.
 dev:
-	./scripts/develop.sh
+	@echo Please run ./scripts/develop.sh manually.
 .PHONY: dev
 
 fmt/prettier:
diff --git a/scripts/develop.sh b/scripts/develop.sh
index 3b4cc5c0d5376..b784cf2ae7634 100755
--- a/scripts/develop.sh
+++ b/scripts/develop.sh
@@ -1,10 +1,21 @@
 #!/usr/bin/env bash
 
+# Allow toggling verbose output
+[[ -n ${VERBOSE:-""} ]] && set -x
 set -euo pipefail
-set -x
 
 SCRIPT_DIR=$(dirname "${BASH_SOURCE[0]}")
+# shellcheck disable=SC1091
+source "${SCRIPT_DIR}/lib.sh"
 PROJECT_ROOT=$(cd "$SCRIPT_DIR" && git rev-parse --show-toplevel)
+set +u
+CODER_DEV_ADMIN_PASSWORD="${CODER_DEV_ADMIN_PASSWORD:-password}"
+set -u
+
+# Preflight checks: ensure we have our required dependencies, and make sure nothing is listening on port 3000 or 8080
+dependencies curl git go make nc yarn
+nc -z 127.0.0.1 3000 >/dev/null 2>&1 && echo '== ERROR: something is listening on port 3000. Kill it and re-run this script.' && exit 1
+nc -z 127.0.0.1 8080 >/dev/null 2>&1 && echo '== ERROR: something is listening on port 8080. Kill it and re-run this script.' && exit 1
 
 echo '== Run "make build" before running this command to build binaries.'
 echo '== Without these binaries, workspaces will fail to start!'
@@ -16,19 +27,20 @@ echo '== Without these binaries, workspaces will fail to start!'
 # to kill both at the same time. For more details, see:
 # https://stackoverflow.com/questions/3004811/how-do-you-run-multiple-programs-in-parallel-from-a-bash-script
 (
+	SCRIPT_PID=$$
 	cd "${PROJECT_ROOT}"
+	CODERV2_HOST=http://127.0.0.1:3000 INSPECT_XSTATE=true yarn --cwd=./site dev || kill -INT -${SCRIPT_PID} &
+	go run -tags embed cmd/coder/main.go server --address 127.0.0.1:3000 --in-memory --tunnel || kill -INT -${SCRIPT_PID} &
 
-	trap 'kill 0' SIGINT
-	CODERV2_HOST=http://127.0.0.1:3000 INSPECT_XSTATE=true yarn --cwd=./site dev &
-	go run -tags embed cmd/coder/main.go server --in-memory --tunnel &
-
-	# Just a minor sleep to ensure the first user was created to make the member.
-	sleep 2
+	echo '== Waiting for Coder to become ready'
+	timeout 60s bash -c 'until curl -s --fail http://localhost:3000 > /dev/null 2>&1; do sleep 0.5; done'
 
 	#  create the first user, the admin
-	go run cmd/coder/main.go login http://127.0.0.1:3000 --username=admin --email=admin@coder.com --password=password || true
+	go run cmd/coder/main.go login http://127.0.0.1:3000 --username=admin --email=admin@coder.com --password="${CODER_DEV_ADMIN_PASSWORD}" ||
+		echo 'Failed to create admin user. To troubleshoot, try running this command manually.'
 
-	# || yes to always exit code 0. If this fails, whelp.
-	go run cmd/coder/main.go users create --email=member@coder.com --username=member --password="${CODER_DEV_ADMIN_PASSWORD}" || true
+	# || true to always exit code 0. If this fails, whelp.
+	go run cmd/coder/main.go users create --email=member@coder.com --username=member --password="${CODER_DEV_ADMIN_PASSWORD}" ||
+		echo 'Failed to create regular user. To troubleshoot, try running this command manually.'
 	wait
 )