diff --git a/home-manager/services/neverssl-keepalive/keepalive.sh b/home-manager/services/neverssl-keepalive/keepalive.sh
index d18f3bc41..68a805666 100755
--- a/home-manager/services/neverssl-keepalive/keepalive.sh
+++ b/home-manager/services/neverssl-keepalive/keepalive.sh
@@ -6,3 +6,15 @@ set -euo pipefail
 
 # Silently ping neverssl.com - ignore failures (network may be unavailable)
 curl -fsS --max-time 10 http://neverssl.com >/dev/null 2>&1 || true
+
+# macOS-specific: Open captive portal for Starbucks WiFi if connectivity is lost
+if [[ $OSTYPE == "darwin"* ]]; then
+  SSID=$(networksetup -getairportnetwork en0 2>/dev/null | awk -F": " '{print $2}' || echo "")
+
+  # Check for Starbucks networks (e.g., at_STARBUCKS_Wi2)
+  if [[ $SSID == *"STARBUCKS"* ]]; then
+    if ! ping -c 1 -W 2 1.1.1.1 >/dev/null 2>&1; then
+      open "http://captive.apple.com" 2>/dev/null || true
+    fi
+  fi
+fi
diff --git a/spec/keepalive_spec.sh b/spec/keepalive_spec.sh
index e95e8c757..c2c3fcdd6 100644
--- a/spec/keepalive_spec.sh
+++ b/spec/keepalive_spec.sh
@@ -83,4 +83,27 @@ The output should include 'captive portal'
 End
 End
 
+Describe 'Starbucks WiFi detection (macOS)'
+It 'checks for macOS via OSTYPE'
+When run bash -c "cat '$SCRIPT'"
+The output should include 'OSTYPE'
+The output should include 'darwin'
+End
+
+It 'uses networksetup to get SSID'
+When run bash -c "cat '$SCRIPT'"
+The output should include 'networksetup -getairportnetwork'
+End
+
+It 'checks for STARBUCKS SSID pattern'
+When run bash -c "cat '$SCRIPT'"
+The output should include '*"STARBUCKS"*'
+End
+
+It 'opens captive portal when connectivity fails'
+When run bash -c "cat '$SCRIPT'"
+The output should include 'captive.apple.com'
+End
+End
+
 End