diff --git a/internal/command/dev/dev.go b/internal/command/dev/dev.go
index 6698954..fa2fb0e 100644
--- a/internal/command/dev/dev.go
+++ b/internal/command/dev/dev.go
@@ -54,10 +54,10 @@ func runDev(cmd *cobra.Command, args []string) error {
 	devController, devWorker, err := CreateDevControllerAndWorker(devDataDirPath,
 		fmt.Sprintf(":%d", netconstants.DefaultControllerPort), resources,
 		nil, nil)
-
 	if err != nil {
 		return err
 	}
+	defer devWorker.Close()
 
 	errChan := make(chan error, 2)
 
diff --git a/internal/command/list/vms.go b/internal/command/list/vms.go
index ac8ac19..0147e13 100644
--- a/internal/command/list/vms.go
+++ b/internal/command/list/vms.go
@@ -40,13 +40,13 @@ func runListVMs(cmd *cobra.Command, args []string) error {
 
 	table := uitable.New()
 
-	table.AddRow("Name", "Created", "Image", "Status", "Restart policy")
+	table.AddRow("Name", "Created", "Image", "Status", "Restart policy", "Assigned worker")
 
 	for _, vm := range vms {
 		restartPolicyInfo := fmt.Sprintf("%s (%d restarts)", vm.RestartPolicy, vm.RestartCount)
 		createdAtInfo := humanize.RelTime(vm.CreatedAt, time.Now(), "ago", "in the future")
 
-		table.AddRow(vm.Name, createdAtInfo, vm.Image, vm.Status, restartPolicyInfo)
+		table.AddRow(vm.Name, createdAtInfo, vm.Image, vm.Status, restartPolicyInfo, vm.Worker)
 	}
 
 	fmt.Println(table)
diff --git a/internal/command/worker/run.go b/internal/command/worker/run.go
index 81be0bd..8a91663 100644
--- a/internal/command/worker/run.go
+++ b/internal/command/worker/run.go
@@ -105,6 +105,7 @@ func runWorker(cmd *cobra.Command, args []string) (err error) {
 	if err != nil {
 		return err
 	}
+	defer workerInstance.Close()
 
 	return workerInstance.Run(cmd.Context())
 }
diff --git a/internal/worker/vmmanager/vm.go b/internal/worker/vmmanager/vm.go
index 54ba2d8..8f4b2ec 100644
--- a/internal/worker/vmmanager/vm.go
+++ b/internal/worker/vmmanager/vm.go
@@ -190,22 +190,23 @@ func (vm *VM) IP(ctx context.Context) (string, error) {
 	return strings.TrimSpace(stdout), nil
 }
 
-func (vm *VM) Stop() error {
+func (vm *VM) Stop() {
 	if !vm.cloned {
-		return nil
+		return
 	}
 
 	vm.logger.Debugf("stopping VM")
 
-	_, _, _ = tart.Tart(context.Background(), vm.logger, "stop", vm.id())
+	_, _, err := tart.Tart(context.Background(), vm.logger, "stop", vm.id())
+	if err != nil {
+		vm.logger.Warnf("failed to stop VM: %v", err)
+	}
 
 	vm.logger.Debugf("VM stopped")
 
 	vm.cancel()
 
 	vm.wg.Wait()
-
-	return nil
 }
 
 func (vm *VM) Delete() error {
diff --git a/internal/worker/worker.go b/internal/worker/worker.go
index 0ed6ed6..7cf1305 100644
--- a/internal/worker/worker.go
+++ b/internal/worker/worker.go
@@ -86,10 +86,7 @@ func (worker *Worker) Run(ctx context.Context) error {
 func (worker *Worker) Close() error {
 	var result error
 	for _, vm := range worker.vmm.List() {
-		err := vm.Stop()
-		if err != nil {
-			result = multierror.Append(result, err)
-		}
+		vm.Stop()
 	}
 	for _, vm := range worker.vmm.List() {
 		err := vm.Delete()
@@ -188,6 +185,7 @@ func (worker *Worker) updateWorker(ctx context.Context) error {
 	return nil
 }
 
+//nolint:nestif // nested "if" complexity is tolerable for now
 func (worker *Worker) syncVMs(ctx context.Context) error {
 	remoteVMs, err := worker.client.VMs().FindForWorker(ctx, worker.name)
 	if err != nil {
@@ -199,8 +197,12 @@ func (worker *Worker) syncVMs(ctx context.Context) error {
 	}
 
 	worker.logger.Infof("syncing %d local VMs against %d remote VMs...",
-		len(remoteVMsIndex), worker.vmm.Len())
+		worker.vmm.Len(), len(remoteVMsIndex))
 
+	// It's important to check the remote VMs against local ones first
+	// to stop the failed VMs before we start the new VMs, otherwise we
+	// risk violating the resource constraints (e.g. a maximum of 2 VMs
+	// per host)
 	for _, vm := range worker.vmm.List() {
 		remoteVM, ok := remoteVMsIndex[vm.OnDiskName()]
 		if !ok {
@@ -211,12 +213,22 @@ func (worker *Worker) syncVMs(ctx context.Context) error {
 			if err := worker.deleteVM(vm); err != nil {
 				return err
 			}
-		} else if remoteVM.Status != v1.VMStatusFailed && vm.Err() != nil {
-			// Local VM has failed, update remote VM
-			remoteVM.Status = v1.VMStatusFailed
-			remoteVM.StatusMessage = vm.Err().Error()
-			if _, err := worker.client.VMs().Update(ctx, remoteVM); err != nil {
-				return err
+		} else {
+			if remoteVM.Status == v1.VMStatusFailed {
+				// VM has failed on the remote side, stop it locally to prevent incorrect
+				// worker's resources calculation in the Controller's scheduler
+				vm.Stop()
+			} else if vm.Err() != nil {
+				// VM has failed on the local side, stop it before reporting as failed to prevent incorrect
+				// worker's resources calculation in the Controller's scheduler
+				vm.Stop()
+
+				// Report the VM as failed
+				remoteVM.Status = v1.VMStatusFailed
+				remoteVM.StatusMessage = vm.Err().Error()
+				if _, err := worker.client.VMs().Update(ctx, remoteVM); err != nil {
+					return err
+				}
 			}
 		}
 	}
@@ -238,6 +250,7 @@ func (worker *Worker) syncVMs(ctx context.Context) error {
 	return nil
 }
 
+//nolint:nestif,gocognit // complexity is tolerable for now
 func (worker *Worker) syncOnDiskVMs(ctx context.Context) error {
 	remoteVMs, err := worker.client.VMs().FindForWorker(ctx, worker.name)
 	if err != nil {
@@ -256,10 +269,6 @@ func (worker *Worker) syncOnDiskVMs(ctx context.Context) error {
 	}
 
 	for _, vmInfo := range vmInfos {
-		if vmInfo.Running {
-			continue
-		}
-
 		onDiskName, err := ondiskname.Parse(vmInfo.Name)
 		if err != nil {
 			if errors.Is(err, ondiskname.ErrNotManagedByOrchard) {
@@ -269,22 +278,44 @@ func (worker *Worker) syncOnDiskVMs(ctx context.Context) error {
 			return err
 		}
 
+		// VMs that exist in the Worker's VM manager will be handled in the syncVMs()
+		if worker.vmm.Exists(onDiskName) {
+			continue
+		}
+
 		remoteVM, ok := remoteVMsIndex[onDiskName]
 		if !ok {
-			// On-disk VM doesn't exist on the controller, delete it
+			// On-disk VM doesn't exist on the controller nor in the Worker's VM manager,
+			// stop it (if applicable) and delete it
+			if vmInfo.Running {
+				_, _, err := tart.Tart(ctx, worker.logger, "stop", vmInfo.Name)
+				if err != nil {
+					worker.logger.Warnf("failed to stop")
+				}
+			}
+
 			_, _, err := tart.Tart(ctx, worker.logger, "delete", vmInfo.Name)
 			if err != nil {
 				return err
 			}
-		} else if remoteVM.Status == v1.VMStatusRunning && !worker.vmm.Exists(onDiskName) {
-			// On-disk VM exist on the controller,
-			// but we don't know about it, so
-			// mark it as failed
-			remoteVM.Status = v1.VMStatusFailed
-			remoteVM.StatusMessage = "Worker lost track of VM"
-			_, err := worker.client.VMs().Update(ctx, remoteVM)
-			if err != nil {
-				return err
+		} else if remoteVM.Status != v1.VMStatusPending {
+			// On-disk VM exists on the controller and was acted upon,
+			// but we've lost track of it, so shut it down (if applicable)
+			// and report the error (if not failed yet)
+			if vmInfo.Running {
+				_, _, err := tart.Tart(ctx, worker.logger, "stop", vmInfo.Name)
+				if err != nil {
+					worker.logger.Warnf("failed to stop")
+				}
+			}
+
+			if remoteVM.Status != v1.VMStatusFailed {
+				remoteVM.Status = v1.VMStatusFailed
+				remoteVM.StatusMessage = "Worker lost track of VM"
+				_, err := worker.client.VMs().Update(ctx, remoteVM)
+				if err != nil {
+					return err
+				}
 			}
 		}
 	}
@@ -293,9 +324,7 @@ func (worker *Worker) syncOnDiskVMs(ctx context.Context) error {
 }
 
 func (worker *Worker) deleteVM(vm *vmmanager.VM) error {
-	if err := vm.Stop(); err != nil {
-		return err
-	}
+	vm.Stop()
 
 	if err := vm.Delete(); err != nil {
 		return err