diff --git a/saas/exe/stripe-dev b/saas/exe/stripe-dev
index 820264766..c2aea61a4 100755
--- a/saas/exe/stripe-dev
+++ b/saas/exe/stripe-dev
@@ -1,10 +1,30 @@
 #!/usr/bin/env ruby
 #
-# Fetches Stripe development environment variables from 1Password.
+# Fetches Stripe development environment variables from 1Password and starts
+# the Stripe CLI webhook listener.
+#
 # Usage: eval "$(bundle exec stripe-dev)"
 
 require "json"
+require "fileutils"
 
+LOG_FILE = "log/stripe.development.log"
+PID_FILE = "tmp/stripe.tunnel.pid"
+
+# Ensure directories exist
+FileUtils.mkdir_p("log")
+FileUtils.mkdir_p("tmp")
+
+# Kill any existing stripe tunnel process
+if File.exist?(PID_FILE)
+  old_pid = File.read(PID_FILE).strip.to_i
+  if old_pid > 0
+    Process.kill("TERM", old_pid) rescue nil
+  end
+  File.delete(PID_FILE)
+end
+
+# Fetch secrets from 1Password
 secrets_escaped = `kamal secrets fetch \
   --adapter 1password \
   --account basecamp \
@@ -12,12 +32,49 @@ secrets_escaped = `kamal secrets fetch \
   "Development/STRIPE_SECRET_KEY" \
   "Development/STRIPE_MONTHLY_V1_PRICE_ID" 2>/dev/null`
 
-# kamal outputs shell-escaped JSON, unescape it
 secrets_json = secrets_escaped.gsub(/\\(.)/, '\1')
 secrets = JSON.parse(secrets_json)
 
 stripe_secret_key = secrets["Deploy/Fizzy/Development/STRIPE_SECRET_KEY"]
 stripe_price_id = secrets["Deploy/Fizzy/Development/STRIPE_MONTHLY_V1_PRICE_ID"]
 
+# Clear previous log file
+File.write(LOG_FILE, "")
+
+# Start stripe listen in background
+pid = spawn(
+  "stripe", "listen", "--forward-to", "localhost:3006/stripe/webhooks",
+  out: [LOG_FILE, "a"],
+  err: [LOG_FILE, "a"]
+)
+Process.detach(pid)
+
+# Save PID for cleanup
+File.write(PID_FILE, pid.to_s)
+
+# Wait for the webhook secret to appear in logs
+webhook_secret = nil
+20.times do
+  sleep 0.5
+  if File.exist?(LOG_FILE)
+    content = File.read(LOG_FILE)
+    if match = content.match(/webhook signing secret is (whsec_\w+)/)
+      webhook_secret = match[1]
+      break
+    end
+  end
+end
+
+if webhook_secret.nil?
+  warn "Warning: Could not capture webhook secret from stripe listen"
+end
+
+# Output export statements
 puts %Q(export STRIPE_SECRET_KEY="#{stripe_secret_key}")
 puts %Q(export STRIPE_MONTHLY_V1_PRICE_ID="#{stripe_price_id}")
+puts %Q(export STRIPE_WEBHOOK_SECRET="#{webhook_secret}") if webhook_secret
+
+# Informational message to stderr (won't be eval'd)
+warn ""
+warn "Stripe CLI listening (PID: #{pid})"
+warn "Logs: #{LOG_FILE}"