diff --git a/.github/workflows/vagrant.yml b/.github/workflows/vagrant.yml
index bebdcec..9dda974 100644
--- a/.github/workflows/vagrant.yml
+++ b/.github/workflows/vagrant.yml
@@ -8,7 +8,7 @@ on:
 
 jobs:
   homelab-ci:
-    runs-on: macos-latest
+    runs-on: macos-13
 
     steps:
       - uses: actions/checkout@v3
@@ -21,19 +21,59 @@ jobs:
           restore-keys: |
             ${{ runner.os }}-vagrant-
 
+      - name: Install VirtualBox
+        run: brew install --cask virtualbox
+
+      - name: Install Vagrant
+        run: brew install --cask vagrant
+
       - name: Install Ansible
-        run: brew install ansible@7
+        run: brew install ansible
 
       - name: Software Versions
         run: |
-          printf "VirtualBox "
-          vboxmanage --version
+          printf "VirtualBox "; vboxmanage --version
           vagrant --version
-          export PATH="/usr/local/opt/ansible@7/bin:$PATH"
           ansible --version
 
+      - name: Install debugging tools
+        run: brew install nmap tree
+
       - name: Vagrant Up with Dockerbox Playbook
+        env:
+          SSH_AUTH_SOCK: ''
         run: |
-          export PATH="/usr/local/opt/ansible@7/bin:$PATH"
-          PLAYBOOK=dockerbox vagrant up
-          vagrant ssh -c "docker ps"
+          PLAYBOOK=dockerbox vagrant up --debug &
+          VAGRANT_UP_PID=$!
+          DEBUG_ID="[homelab-ci]"
+          echo "$DEBUG_ID Waiting for VM to start..."
+          sleep 60
+          TIMEOUT=600
+          ELAPSED=0
+          SLEEP_DURATION=30
+          SSH_AVAILABLE=0
+          while [[ $ELAPSED -lt $TIMEOUT ]]; do
+            vagrant ssh-config
+            PRIVATE_KEY="$(vagrant ssh-config | grep -E 'IdentityFile.*\.rsa$' | awk '{print $2}')"
+            HOST_IP="$(vagrant ssh-config | grep HostName | awk '{print $2}')"
+            echo "$DEBUG_ID Checking SSH connection availability..."
+            echo "$DEBUG_ID Private Key: $PRIVATE_KEY"
+            echo "$DEBUG_ID Host IP: $HOST_IP"
+            echo "$DEBUG_ID Running nmap to check open ports..."
+            nmap -p 22 "$HOST_IP" | grep "22/tcp open" && SSH_AVAILABLE=1 || SSH_AVAILABLE=0
+            if [[ $SSH_AVAILABLE -eq 1 ]]; then
+              echo "$DEBUG_ID SSH port is open, attempting connection..."
+              ssh -vvv -i "$PRIVATE_KEY" \
+                  -o UserKnownHostsFile=/dev/null \
+                  -o StrictHostKeyChecking=no \
+                  -v vagrant@"$HOST_IP" && break || echo "$DEBUG_ID SSH connection failed, retrying..."
+            else
+              echo "$DEBUG_ID SSH port not open, retrying in $SLEEP_DURATION seconds..."
+            fi
+            sleep $SLEEP_DURATION
+            ((ELAPSED+=SLEEP_DURATION))
+          done
+          if [[ $SSH_AVAILABLE -ne 1 ]]; then
+            echo "$DEBUG_ID Timeout reached without successful SSH connection."
+          fi
+          wait $VAGRANT_UP_PID  # Ensure the Vagrant up process completes
diff --git a/Vagrantfile b/Vagrantfile
index 4da8435..77e5141 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -36,6 +36,7 @@ Vagrant.configure("2") do |config|
   config.vm.provider :virtualbox do |vbox|
     vbox.cpus   = VAGRANT_CPUS
     vbox.memory = VAGRANT_MEM
+    vbox.gui    = true
   end
 
   # Provision with Ansible
@@ -43,6 +44,6 @@ Vagrant.configure("2") do |config|
     ENV['ANSIBLE_ROLES_PATH'] = File.dirname(__FILE__) + "/roles"
     ansible.compatibility_mode = "2.0"
     ansible.playbook = "dev/" + PLAYBOOK + ".yml"
-    ansible.raw_arguments = ["--diff"]
+    ansible.raw_arguments = ["--diff", "-vvv"] 
   end
 end