diff --git a/cli/app/undeploy.go b/cli/app/undeploy.go
index 469682b9..79836d24 100644
--- a/cli/app/undeploy.go
+++ b/cli/app/undeploy.go
@@ -3,6 +3,7 @@ package app
 import (
 	"context"
 	"fmt"
+	"time"
 
 	"coopcloud.tech/abra/cli/internal"
 	"coopcloud.tech/abra/pkg/autocomplete"
@@ -18,7 +19,51 @@ var prune bool
 var pruneFlag = &cli.BoolFlag{
 	Name:        "prune, p",
 	Destination: &prune,
-	Usage:       "Prunes unused containers, networks, and dangling images for stack",
+	Usage:       "Prunes unused containers, networks, and dangling images for an app",
+}
+
+func cleanup(c *cli.Context) 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()
+
+		pruneFilters := filters.NewArgs()
+		stackSearch := fmt.Sprintf("%s*", stackName)
+		pruneFilters.Add("label", stackSearch)
+		cr, err := cl.ContainersPrune(ctx, pruneFilters)
+		if err != nil {
+			logrus.Errorf(err.Error())
+			time.Sleep(time.Second)
+			continue
+		}
+		logrus.Infof("Containers deleted: %s; Space reclaimed: %v", cr.ContainersDeleted, cr.SpaceReclaimed)
+
+		nr, err := cl.NetworksPrune(ctx, pruneFilters)
+		if err != nil {
+			logrus.Errorf(err.Error())
+			time.Sleep(time.Second)
+			continue
+		}
+		logrus.Infof("Networks deleted %s", nr.NetworksDeleted)
+
+		ir, err := cl.ImagesPrune(ctx, pruneFilters)
+		if err != nil {
+			logrus.Errorf(err.Error())
+			time.Sleep(time.Second)
+			continue
+		}
+		logrus.Infof("Images deleted: %s; Space reclaimed: %v", ir.ImagesDeleted, ir.SpaceReclaimed)
+		break
+	}
+	return nil
 }
 
 var appUndeployCommand = cli.Command{
@@ -64,41 +109,7 @@ volumes as eligible for pruning once undeployed.
 		if err := stack.RunRemove(context.Background(), cl, rmOpts); err != nil {
 			logrus.Fatal(err)
 		}
-
-		return nil
-	},
-	After: func(c *cli.Context) error {
-		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()
-
-		pruneFilters := filters.NewArgs()
-		stackSearch := fmt.Sprintf("%s*", stackName)
-		pruneFilters.Add("label", stackSearch)
-		cr, err := cl.ContainersPrune(ctx, pruneFilters)
-		if err != nil {
-			return err
-		}
-		logrus.Infof("Containers deleted: %s; Space reclaimed: %v", cr.ContainersDeleted, cr.SpaceReclaimed)
-
-		nr, err := cl.NetworksPrune(ctx, pruneFilters)
-		if err != nil {
-			return err
-		}
-		logrus.Infof("Networks deleted %s", nr.NetworksDeleted)
-
-		ir, err := cl.ImagesPrune(ctx, pruneFilters)
-		if err != nil {
-			return err
-		}
-		logrus.Infof("Images deleted: %s; Space reclaimed: %v", ir.ImagesDeleted, ir.SpaceReclaimed)
+		cleanup(c)
 		return nil
 	},
 	BashComplete: autocomplete.AppNameComplete,
diff --git a/cli/server/prune.go b/cli/server/prune.go
index 49b2084a..2d59947f 100644
--- a/cli/server/prune.go
+++ b/cli/server/prune.go
@@ -27,13 +27,11 @@ var volumesFilterFlag = &cli.BoolFlag{
 }
 
 var serverPruneCommand = cli.Command{
-	Name:    "prune",
-	Aliases: []string{"p"},
-	Usage:   "Prune a managed server; Runs a docker system prune",
-	Description: `
-	Prunes unused containers, networks, and dangling images
-	`,
-	ArgsUsage: "[<server>]",
+	Name:        "prune",
+	Aliases:     []string{"p"},
+	Usage:       "Prune a managed server; Runs a docker system prune",
+	Description: "Prunes unused containers, networks, and dangling images",
+	ArgsUsage:   "[<server>]",
 	Flags: []cli.Flag{
 		allFilterFlag,
 		volumesFilterFlag,
@@ -47,18 +45,18 @@ var serverPruneCommand = cli.Command{
 
 		cl, err := client.New(serverName)
 		if err != nil {
-			return err
+			logrus.Fatal(err)
 		}
 		ctx := context.Background()
 		cr, err := cl.ContainersPrune(ctx, args)
 		if err != nil {
-			return err
+			logrus.Fatal(err)
 		}
 		logrus.Infof("Containers deleted: %s; Space reclaimed: %v", cr.ContainersDeleted, cr.SpaceReclaimed)
 
 		nr, err := cl.NetworksPrune(ctx, args)
 		if err != nil {
-			return err
+			logrus.Fatal(err)
 		}
 		logrus.Infof("Networks deleted %s", nr.NetworksDeleted)
 
@@ -68,14 +66,14 @@ var serverPruneCommand = cli.Command{
 		}
 		ir, err := cl.ImagesPrune(ctx, pruneFilters)
 		if err != nil {
-			return err
+			logrus.Fatal(err)
 		}
 		logrus.Infof("Images deleted: %s; Space reclaimed: %v", ir.ImagesDeleted, ir.SpaceReclaimed)
 
 		if volunesFilter {
 			vr, err := cl.VolumesPrune(ctx, args)
 			if err != nil {
-				return err
+				logrus.Fatal(err)
 			}
 			logrus.Infof("Volumes deleted: %s; Space reclaimed: %v", vr.VolumesDeleted, vr.SpaceReclaimed)
 		}