diff --git a/GitLab/custom-executor.md b/GitLab/custom-executor.md
index ec33803..90d4549 100644
--- a/GitLab/custom-executor.md
+++ b/GitLab/custom-executor.md
@@ -65,6 +65,7 @@ The provided scripts expect the following environment variables to be set:
 - `CUSTOM_ENV_ORKA_VM_NAME_PREFIX` - The prefix of the generated VM name. Defaults to `gl-runner`.
 - `CUSTOM_ENV_ORKA_VM_USER` - User used to SSH to the VM.
 - `CUSTOM_ENV_ORKA_SSH_KEY_FILE` - The private SSH key contents to use when connecting to the VM. This key was created earlier during the Orka base image setup.
+- `CUSTOM_ENV_VM_DEPLOYMENT_ATTEMPTS` - The number of attempts the executor tries to deploy a VM before it fails. Defaults to `1`. Note - GitLab automatically retries 3 times. This env var allows additional retry attempts.
 
 For more information about GitLab CI/CD environment variables, see [here][env-variables].
 
diff --git a/GitLab/scripts/prepare.sh b/GitLab/scripts/prepare.sh
index 3274ce2..8f43a91 100755
--- a/GitLab/scripts/prepare.sh
+++ b/GitLab/scripts/prepare.sh
@@ -6,19 +6,83 @@ currentDir="$( cd "$( dirname "${BASH_SOURCE[0]}" )" >/dev/null 2>&1 && pwd )"
 
 source "${currentDir}/base.sh"
 
+VM_DEPLOYMENT_ATTEMPTS=${CUSTOM_ENV_VM_DEPLOYMENT_ATTEMPTS:-1}
+
 function cleanup_on_failure {
     if [ -f "$BUILD_ID" ]; then
         vm_name=$(<"$BUILD_ID")
-        echo "Failure detected. Cleaning up VM '$vm_name'..."
+        echo "Failure detected. Cleaning up VM '$vm_name'..." >&2
         
-        orka3 vm delete "$vm_name" || echo "Failed to delete VM '$vm_name'"
+        orka3 vm delete "$vm_name" || echo "Failed to delete VM '$vm_name'" >&2
         
-        echo "VM cleanup completed."
+        echo "VM cleanup completed." >&2
     fi
     
     system_failure
 }
 
+function delete_vm_and_cleanup {
+    if [ -f "$BUILD_ID" ]; then
+        vm_name=$(<"$BUILD_ID")
+        echo "Deleting VM '$vm_name'..." >&2
+        orka3 vm delete "$vm_name" || echo "Failed to delete VM '$vm_name'" >&2
+        rm -f "$BUILD_ID"
+        rm -f "$CONNECTION_INFO_ID"
+    fi
+}
+
+function attempt_deployment {
+    local vm_name=$1
+    
+    echo "Deploying VM with name '$vm_name'..."
+    
+    if ! vm_info=$(orka3 vm deploy "$vm_name" --config "$ORKA_CONFIG_NAME" -o json); then
+        echo "VM deployment failed" >&2
+        return 1
+    fi
+    
+    echo "VM deployed successfully."
+    
+    vm_ip=$(echo "$vm_info" | jq -r '.[0]|.ip')
+    vm_ip=$(map_ip "$vm_ip")
+    vm_ssh_port=$(echo "$vm_info" | jq -r '.[0]|.ssh')
+    
+    if ! valid_ip "$vm_ip"; then
+        echo "Invalid ip: $vm_ip" >&2
+        return 1
+    fi
+    
+    if [ -z "$vm_ssh_port" ]; then
+        echo "Invalid port: $vm_ssh_port" >&2
+        return 1
+    fi
+    
+    echo "$vm_ip;$vm_ssh_port" > "$CONNECTION_INFO_ID"
+    
+    echo "Connecting to '$vm_name' ($vm_ip:$vm_ssh_port)"
+    
+    echo "Waiting for SSH access to be available..."
+    local ssh_ready=false
+    for i in $(seq 1 30); do
+        if ssh -i "$ORKA_SSH_KEY_FILE" -o ConnectTimeout=60 -o StrictHostKeyChecking=no -o UserKnownHostsFile=/dev/null "$ORKA_VM_USER@$vm_ip" -p "$vm_ssh_port" "echo ok" >/dev/null 2>&1; then
+            ssh_ready=true
+            break
+        fi
+        sleep 1s
+    done
+    
+    if [ "$ssh_ready" = false ]; then
+        echo 'Waited 30 seconds for sshd to start, exiting...' >&2
+        return 1
+    fi
+    
+    touch ~/.ssh/known_hosts
+    ssh-keygen -R "[$vm_ip]:$vm_ssh_port"
+    ssh-keyscan -t rsa -p "$vm_ssh_port" "$vm_ip" >> ~/.ssh/known_hosts
+    
+    return 0
+}
+
 trap cleanup_on_failure ERR
 
 echo "Authenticating with Orka..."
@@ -28,52 +92,28 @@ orka3 user set-token "$ORKA_TOKEN"
 
 echo "Authenticated."
 
-echo "Generating VM name..."
-
-vm_name=$(generate_vm_name)
-
-echo "Generated VM name: '$vm_name'"
-
-echo "$vm_name" > "$BUILD_ID"
-
-echo "Deploying VM with name '$vm_name'..."
-
-vm_info=$(orka3 vm deploy "$vm_name" --config "$ORKA_CONFIG_NAME" -o json)
-
-echo "VM deployed successfully."
-
-vm_ip=$(echo "$vm_info" | jq -r '.[0]|.ip')
-vm_ip=$(map_ip "$vm_ip")
-vm_ssh_port=$(echo "$vm_info" | jq -r '.[0]|.ssh')
-
-if ! valid_ip "$vm_ip"; then
-    echo "Invalid ip: $vm_ip" 1>&2
-    exit "$SYSTEM_FAILURE_EXIT_CODE"
-fi
-
-if [ -z "$vm_ssh_port" ]; then
-    echo "Invalid port: $vm_ssh_port" 1>&2
-    exit "$SYSTEM_FAILURE_EXIT_CODE"
-fi
-
-echo "$vm_ip;$vm_ssh_port" > "$CONNECTION_INFO_ID"
-
-echo "Connecting to '$vm_name' ($vm_ip:$vm_ssh_port)"
-
-echo "Waiting for SSH access to be available..."
-for i in $(seq 1 30); do
-    if ssh -i "$ORKA_SSH_KEY_FILE" -o ConnectTimeout=60 -o StrictHostKeyChecking=no -o UserKnownHostsFile=/dev/null "$ORKA_VM_USER@$vm_ip" -p "$vm_ssh_port" "echo ok" >/dev/null 2>&1; then
+for attempt in $(seq 1 "$VM_DEPLOYMENT_ATTEMPTS"); do
+    echo "Deployment attempt $attempt of $VM_DEPLOYMENT_ATTEMPTS"
+    
+    echo "Generating VM name..."
+    vm_name=$(generate_vm_name)
+    echo "Generated VM name: '$vm_name'"
+    echo "$vm_name" > "$BUILD_ID"
+    
+    if attempt_deployment "$vm_name"; then
+        echo "Deployment successful on attempt $attempt"
         break
+    else
+        echo "Deployment attempt $attempt failed"
+        
+        delete_vm_and_cleanup
+        
+        if [ "$attempt" -eq "$VM_DEPLOYMENT_ATTEMPTS" ]; then
+            echo "All deployment attempts failed. Exiting..." >&2
+            exit "$SYSTEM_FAILURE_EXIT_CODE"
+        else
+            echo "Retrying deployment..."
+            sleep 2
+        fi
     fi
-
-    if [ "$i" == "30" ]; then
-        echo 'Waited 30 seconds for sshd to start, exiting...' 1>&2
-        exit "$SYSTEM_FAILURE_EXIT_CODE"
-    fi
-
-    sleep 1s
 done
-
-touch ~/.ssh/known_hosts
-ssh-keygen -R "[$vm_ip]:$vm_ssh_port"
-ssh-keyscan -t rsa -p "$vm_ssh_port" "$vm_ip" >> ~/.ssh/known_hosts