diff --git a/cli/app/undeploy.go b/cli/app/undeploy.go
index 79836d24..3abf5304 100644
--- a/cli/app/undeploy.go
+++ b/cli/app/undeploy.go
@@ -8,8 +8,10 @@ import (
 	"coopcloud.tech/abra/cli/internal"
 	"coopcloud.tech/abra/pkg/autocomplete"
 	"coopcloud.tech/abra/pkg/client"
+	"coopcloud.tech/abra/pkg/config"
 	stack "coopcloud.tech/abra/pkg/upstream/stack"
 	"github.com/docker/docker/api/types/filters"
+	dockerClient "github.com/docker/docker/client"
 	"github.com/sirupsen/logrus"
 	"github.com/urfave/cli"
 )
@@ -22,19 +24,19 @@ var pruneFlag = &cli.BoolFlag{
 	Usage:       "Prunes unused containers, networks, and dangling images for an app",
 }
 
-func cleanup(c *cli.Context) error {
+// pruneSystem runs the equivalent of a "docker system prune" after undeploying
+// in order to clean up left over state related to the deployment. We must run
+// this logic inside a loop as it may take some time for the undeployed to come
+// down.
+func pruneSystem(c *cli.Context, cl *dockerClient.Client, app config.App) error {
 	for {
 		if !prune {
 			return nil
 		}
-		app := internal.ValidateApp(c)
-		stackName := app.StackName()
-		cl, err := client.New(app.Server)
-		if err != nil {
-			logrus.Fatal(err)
-		}
-		ctx := context.Background()
 
+		stackName := app.StackName()
+
+		ctx := context.Background()
 		pruneFilters := filters.NewArgs()
 		stackSearch := fmt.Sprintf("%s*", stackName)
 		pruneFilters.Add("label", stackSearch)
@@ -44,7 +46,8 @@ func cleanup(c *cli.Context) error {
 			time.Sleep(time.Second)
 			continue
 		}
-		logrus.Infof("Containers deleted: %s; Space reclaimed: %v", cr.ContainersDeleted, cr.SpaceReclaimed)
+
+		logrus.Infof("containers deleted: %s; space reclaimed: %v", cr.ContainersDeleted, cr.SpaceReclaimed)
 
 		nr, err := cl.NetworksPrune(ctx, pruneFilters)
 		if err != nil {
@@ -52,7 +55,8 @@ func cleanup(c *cli.Context) error {
 			time.Sleep(time.Second)
 			continue
 		}
-		logrus.Infof("Networks deleted %s", nr.NetworksDeleted)
+
+		logrus.Infof("networks deleted %s", nr.NetworksDeleted)
 
 		ir, err := cl.ImagesPrune(ctx, pruneFilters)
 		if err != nil {
@@ -60,9 +64,12 @@ func cleanup(c *cli.Context) error {
 			time.Sleep(time.Second)
 			continue
 		}
-		logrus.Infof("Images deleted: %s; Space reclaimed: %v", ir.ImagesDeleted, ir.SpaceReclaimed)
+
+		logrus.Infof("images deleted: %s; space reclaimed: %v", ir.ImagesDeleted, ir.SpaceReclaimed)
+
 		break
 	}
+
 	return nil
 }
 
@@ -75,8 +82,9 @@ var appUndeployCommand = cli.Command{
 		internal.NoInputFlag,
 		pruneFlag,
 	},
-	Before: internal.SubCommandBefore,
-	Usage:  "Undeploy an app",
+	Before:       internal.SubCommandBefore,
+	Usage:        "Undeploy an app",
+	BashComplete: autocomplete.AppNameComplete,
 	Description: `
 This does not destroy any of the application data. However, you should remain
 vigilant, as your swarm installation will consider any previously attached
@@ -109,8 +117,11 @@ volumes as eligible for pruning once undeployed.
 		if err := stack.RunRemove(context.Background(), cl, rmOpts); err != nil {
 			logrus.Fatal(err)
 		}
-		cleanup(c)
+
+		if err := pruneSystem(c, cl, app); err != nil {
+			logrus.Fatal(err)
+		}
+
 		return nil
 	},
-	BashComplete: autocomplete.AppNameComplete,
 }