diff --git a/cli/app/deploy.go b/cli/app/deploy.go
index fb72c0ec..87feae8f 100644
--- a/cli/app/deploy.go
+++ b/cli/app/deploy.go
@@ -196,6 +196,7 @@ recipes.
 			Namespace:    stackName,
 			Prune:        false,
 			ResolveImage: stack.ResolveImageAlways,
+			Detach:       false,
 		}
 		compose, err := config.GetAppComposeConfig(app.Name, deployOpts, app.Env)
 		if err != nil {
diff --git a/cli/app/rollback.go b/cli/app/rollback.go
index f39d114b..43b1fbba 100644
--- a/cli/app/rollback.go
+++ b/cli/app/rollback.go
@@ -215,6 +215,7 @@ recipes.
 			Namespace:    stackName,
 			Prune:        false,
 			ResolveImage: stack.ResolveImageAlways,
+			Detach:       false,
 		}
 		compose, err := config.GetAppComposeConfig(app.Name, deployOpts, app.Env)
 		if err != nil {
diff --git a/cli/app/undeploy.go b/cli/app/undeploy.go
index 3a1c2ffa..7b50908d 100644
--- a/cli/app/undeploy.go
+++ b/cli/app/undeploy.go
@@ -122,7 +122,10 @@ Passing "-p/--prune" does not remove those volumes.
 			logrus.Fatal(err)
 		}
 
-		rmOpts := stack.Remove{Namespaces: []string{app.StackName()}}
+		rmOpts := stack.Remove{
+			Namespaces: []string{app.StackName()},
+			Detach:     false,
+		}
 		if err := stack.RunRemove(context.Background(), cl, rmOpts); err != nil {
 			logrus.Fatal(err)
 		}
diff --git a/cli/app/upgrade.go b/cli/app/upgrade.go
index 366a5932..e2f6df6c 100644
--- a/cli/app/upgrade.go
+++ b/cli/app/upgrade.go
@@ -249,6 +249,7 @@ recipes.
 			Namespace:    stackName,
 			Prune:        false,
 			ResolveImage: stack.ResolveImageAlways,
+			Detach:       false,
 		}
 		compose, err := config.GetAppComposeConfig(app.Name, deployOpts, app.Env)
 		if err != nil {
diff --git a/cli/updater/updater.go b/cli/updater/updater.go
index 4b036132..74266d8b 100644
--- a/cli/updater/updater.go
+++ b/cli/updater/updater.go
@@ -362,6 +362,7 @@ func createDeployConfig(recipeName string, stackName string, env config.AppEnv)
 		Namespace:    stackName,
 		Prune:        false,
 		ResolveImage: stack.ResolveImageAlways,
+		Detach:       false,
 	}
 
 	composeFiles, err := config.GetComposeFiles(recipeName, env)
diff --git a/go.mod b/go.mod
index 7347c815..a7e1c3a1 100644
--- a/go.mod
+++ b/go.mod
@@ -7,7 +7,7 @@ require (
 	git.coopcloud.tech/coop-cloud/godotenv v1.5.2-0.20231130100509-01bff8284355
 	github.com/AlecAivazis/survey/v2 v2.3.7
 	github.com/Gurpartap/logrus-stack v0.0.0-20170710170904-89c00d8a28f4
-	github.com/distribution/distribution v2.8.3+incompatible
+	github.com/distribution/reference v0.6.0
 	github.com/docker/cli v26.1.4+incompatible
 	github.com/docker/docker v26.1.4+incompatible
 	github.com/docker/go-units v0.5.0
@@ -36,7 +36,6 @@ require (
 	github.com/cpuguy83/go-md2man/v2 v2.0.4 // indirect
 	github.com/cyphar/filepath-securejoin v0.2.5 // indirect
 	github.com/davecgh/go-spew v1.1.1 // indirect
-	github.com/distribution/reference v0.6.0 // indirect
 	github.com/docker/distribution v2.7.1+incompatible // indirect
 	github.com/docker/go v1.5.1-1.0.20160303222718-d30aec9fd63c // indirect
 	github.com/docker/go-connections v0.5.0 // indirect
diff --git a/go.sum b/go.sum
index be044761..fff7c0bf 100644
--- a/go.sum
+++ b/go.sum
@@ -297,8 +297,6 @@ github.com/denverdino/aliyungo v0.0.0-20190125010748-a747050bb1ba/go.mod h1:dV8l
 github.com/dgrijalva/jwt-go v0.0.0-20170104182250-a601269ab70c/go.mod h1:E3ru+11k8xSBh+hMPgOLZmtrrCbhqsmaPHjLKYnJCaQ=
 github.com/dgrijalva/jwt-go v3.2.0+incompatible/go.mod h1:E3ru+11k8xSBh+hMPgOLZmtrrCbhqsmaPHjLKYnJCaQ=
 github.com/dgryski/go-sip13 v0.0.0-20181026042036-e10d5fee7954/go.mod h1:vAd38F8PWV+bWy6jNmig1y/TA+kYO4g3RSRF0IAv0no=
-github.com/distribution/distribution v2.8.3+incompatible h1:RlpEXBLq/WPXYvBYMDAmBX/SnhD67qwtvW/DzKc8pAo=
-github.com/distribution/distribution v2.8.3+incompatible/go.mod h1:EgLm2NgWtdKgzF9NpMzUKgzmR7AMmb0VQi2B+ZzDRjc=
 github.com/distribution/reference v0.6.0 h1:0IXCQ5g4/QMHHkarYzh5l+u8T3t73zM5QvfrDyIgxBk=
 github.com/distribution/reference v0.6.0/go.mod h1:BbU0aIcezP1/5jX/8MP0YiH4SdvB5Y4f/wlDRiLyi3E=
 github.com/dnaeon/go-vcr v1.0.1/go.mod h1:aBB1+wY4s93YsC3HHjMBMrwTj2R9FHDzUr9KyGc8n1E=
diff --git a/pkg/upstream/stack/options.go b/pkg/upstream/stack/options.go
index 14ca364e..39245eb4 100644
--- a/pkg/upstream/stack/options.go
+++ b/pkg/upstream/stack/options.go
@@ -7,9 +7,12 @@ type Deploy struct {
 	ResolveImage     string
 	SendRegistryAuth bool
 	Prune            bool
+	Detach           bool
+	Quiet            bool
 }
 
 // Remove holds docker stack remove options
 type Remove struct {
 	Namespaces []string
+	Detach     bool
 }
diff --git a/pkg/upstream/stack/remove.go b/pkg/upstream/stack/remove.go
index 6b0f043c..7c211b56 100644
--- a/pkg/upstream/stack/remove.go
+++ b/pkg/upstream/stack/remove.go
@@ -9,6 +9,7 @@ import (
 	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/api/types/swarm"
 	"github.com/docker/docker/api/types/versions"
+	"github.com/docker/docker/client"
 	apiclient "github.com/docker/docker/client"
 	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
@@ -56,6 +57,12 @@ func RunRemove(ctx context.Context, client *apiclient.Client, opts Remove) error
 
 		if hasError {
 			errs = append(errs, fmt.Sprintf("failed to remove some resources from stack: %s", namespace))
+			continue
+		}
+
+		err = waitOnTasks(ctx, client, namespace)
+		if err != nil {
+			errs = append(errs, fmt.Sprintf("failed to wait on tasks of stack: %s: %s", namespace, err))
 		}
 	}
 
@@ -136,3 +143,50 @@ func removeConfigs(
 	}
 	return hasError
 }
+
+// https://github.com/docker/cli/pull/4259
+func getStackTasks(ctx context.Context, apiclient client.APIClient, namespace string) ([]swarm.Task, error) {
+	return apiclient.TaskList(ctx, types.TaskListOptions{Filters: getStackFilter(namespace)})
+}
+
+var numberedStates = map[swarm.TaskState]int64{
+	swarm.TaskStateNew:       1,
+	swarm.TaskStateAllocated: 2,
+	swarm.TaskStatePending:   3,
+	swarm.TaskStateAssigned:  4,
+	swarm.TaskStateAccepted:  5,
+	swarm.TaskStatePreparing: 6,
+	swarm.TaskStateReady:     7,
+	swarm.TaskStateStarting:  8,
+	swarm.TaskStateRunning:   9,
+	swarm.TaskStateComplete:  10,
+	swarm.TaskStateShutdown:  11,
+	swarm.TaskStateFailed:    12,
+	swarm.TaskStateRejected:  13,
+}
+
+func terminalState(state swarm.TaskState) bool {
+	return numberedStates[state] > numberedStates[swarm.TaskStateRunning]
+}
+
+func waitOnTasks(ctx context.Context, client apiclient.APIClient, namespace string) error {
+	terminalStatesReached := 0
+	for {
+		tasks, err := getStackTasks(ctx, client, namespace)
+		if err != nil {
+			return fmt.Errorf("failed to get tasks: %w", err)
+		}
+
+		for _, task := range tasks {
+			if terminalState(task.Status.State) {
+				terminalStatesReached++
+				break
+			}
+		}
+
+		if terminalStatesReached == len(tasks) {
+			break
+		}
+	}
+	return nil
+}
diff --git a/pkg/upstream/stack/stack.go b/pkg/upstream/stack/stack.go
index d8e7bdd9..d9dc94f3 100644
--- a/pkg/upstream/stack/stack.go
+++ b/pkg/upstream/stack/stack.go
@@ -9,6 +9,8 @@ import (
 	"os/signal"
 	"time"
 
+	stdlibErr "errors"
+
 	"coopcloud.tech/abra/pkg/upstream/convert"
 	"github.com/docker/cli/cli/command/service/progress"
 	"github.com/docker/cli/cli/command/stack/formatter"
@@ -129,7 +131,7 @@ func IsDeployed(ctx context.Context, cl *dockerClient.Client, stackName string)
 func pruneServices(ctx context.Context, cl *dockerClient.Client, namespace convert.Namespace, services map[string]struct{}) {
 	oldServices, err := GetStackServices(ctx, cl, namespace.Name())
 	if err != nil {
-		logrus.Infof("Failed to list services: %s\n", err)
+		logrus.Infof("failed to list services: %s\n", err)
 	}
 
 	pruneServices := []swarm.Service{}
@@ -161,7 +163,7 @@ func validateResolveImageFlag(opts *Deploy) error {
 	case ResolveImageAlways, ResolveImageChanged, ResolveImageNever:
 		return nil
 	default:
-		return errors.Errorf("Invalid option %s for flag --resolve-image", opts.ResolveImage)
+		return errors.Errorf("invalid option %s for flag --resolve-image", opts.ResolveImage)
 	}
 }
 
@@ -206,7 +208,16 @@ func deployCompose(ctx context.Context, cl *dockerClient.Client, opts Deploy, co
 		return err
 	}
 
-	return deployServices(ctx, cl, services, namespace, opts.SendRegistryAuth, opts.ResolveImage, appName, dontWait)
+	serviceIDs, err := deployServices(ctx, cl, services, namespace, opts.SendRegistryAuth, opts.ResolveImage, appName, dontWait)
+	if err != nil {
+		return err
+	}
+
+	logrus.Infof("waiting for %s to deploy... please hold 🤚", appName)
+	if err := waitOnServices(ctx, cl, serviceIDs, appName); err == nil {
+		logrus.Infof("Successfully deployed %s", appName)
+	}
+	return err
 }
 
 func getServicesDeclaredNetworks(serviceConfigs []composetypes.ServiceConfig) map[string]struct{} {
@@ -276,7 +287,7 @@ func createConfigs(ctx context.Context, cl *dockerClient.Client, configs []swarm
 			}
 		case dockerClient.IsErrNotFound(err):
 			// config does not exist, then we create a new one.
-			logrus.Infof("Creating config %s\n", configSpec.Name)
+			logrus.Infof("creating config %s\n", configSpec.Name)
 			if _, err := cl.ConfigCreate(ctx, configSpec); err != nil {
 				return errors.Wrapf(err, "failed to create config %s", configSpec.Name)
 			}
@@ -307,7 +318,7 @@ func createNetworks(ctx context.Context, cl *dockerClient.Client, namespace conv
 			createOpts.Driver = defaultNetworkDriver
 		}
 
-		logrus.Infof("Creating network %s\n", name)
+		logrus.Infof("creating network %s\n", name)
 		if _, err := cl.NetworkCreate(ctx, name, createOpts); err != nil {
 			return errors.Wrapf(err, "failed to create network %s", name)
 		}
@@ -323,10 +334,10 @@ func deployServices(
 	sendAuth bool,
 	resolveImage string,
 	appName string,
-	dontWait bool) error {
+	dontWait bool) ([]string, error) {
 	existingServices, err := GetStackServices(ctx, cl, namespace.Name())
 	if err != nil {
-		return err
+		return nil, err
 	}
 
 	existingServiceMap := make(map[string]swarm.Service)
@@ -334,7 +345,8 @@ func deployServices(
 		existingServiceMap[service.Spec.Name] = service
 	}
 
-	serviceIDs := make(map[string]string)
+	var serviceIDs []string
+
 	for internalName, serviceSpec := range services {
 		var (
 			name        = namespace.Scope(internalName)
@@ -378,16 +390,16 @@ func deployServices(
 
 			response, err := cl.ServiceUpdate(ctx, service.ID, service.Version, serviceSpec, updateOpts)
 			if err != nil {
-				return errors.Wrapf(err, "failed to update service %s", name)
+				return nil, errors.Wrapf(err, "failed to update service %s", name)
 			}
 
-			serviceIDs[service.ID] = name
-
 			for _, warning := range response.Warnings {
 				logrus.Warn(warning)
 			}
+
+			serviceIDs = append(serviceIDs, service.ID)
 		} else {
-			logrus.Infof("Creating service %s\n", name)
+			logrus.Infof("creating service %s\n", name)
 
 			createOpts := types.ServiceCreateOptions{EncodedRegistryAuth: encodedAuth}
 
@@ -398,43 +410,19 @@ func deployServices(
 
 			serviceCreateResponse, err := cl.ServiceCreate(ctx, serviceSpec, createOpts)
 			if err != nil {
-				return errors.Wrapf(err, "failed to create service %s", name)
+				return nil, errors.Wrapf(err, "failed to create service %s", name)
 			}
 
-			serviceIDs[serviceCreateResponse.ID] = name
+			serviceIDs = append(serviceIDs, serviceCreateResponse.ID)
 		}
 	}
 
-	var serviceNames []string
-	for _, serviceName := range serviceIDs {
-		serviceNames = append(serviceNames, serviceName)
-	}
-
 	if dontWait {
 		logrus.Warn("skipping converge logic checks")
-		return nil
+		return nil, nil
 	}
 
-	logrus.Infof("Waiting for %s to deploy... please hold 🤚", appName)
-	ch := make(chan error, len(serviceIDs))
-	for serviceID, serviceName := range serviceIDs {
-		logrus.Debugf("waiting on %s to converge", serviceName)
-		go func(sID, sName, aName string) {
-			ch <- WaitOnService(ctx, cl, sID, aName)
-		}(serviceID, serviceName, appName)
-	}
-
-	for _, serviceID := range serviceIDs {
-		err := <-ch
-		if err != nil {
-			return err
-		}
-		logrus.Debugf("assuming %s converged successfully", serviceID)
-	}
-
-	logrus.Infof("Successfully deployed %s", appName)
-
-	return nil
+	return serviceIDs, nil
 }
 
 func getStackNetworks(ctx context.Context, dockerclient client.APIClient, namespace string) ([]types.NetworkResource, error) {
@@ -449,6 +437,22 @@ func getStackConfigs(ctx context.Context, dockerclient client.APIClient, namespa
 	return dockerclient.ConfigList(ctx, types.ConfigListOptions{Filters: getStackFilter(namespace)})
 }
 
+func waitOnServices(ctx context.Context, cl *dockerClient.Client, serviceIDs []string, appName string) error {
+	var errs []error
+
+	for _, serviceID := range serviceIDs {
+		if err := WaitOnService(ctx, cl, serviceID, appName); err != nil {
+			errs = append(errs, fmt.Errorf("%s: %w", serviceID, err))
+		}
+	}
+
+	if len(errs) > 0 {
+		return stdlibErr.Join(errs...)
+	}
+
+	return nil
+}
+
 // https://github.com/docker/cli/blob/master/cli/command/service/helpers.go
 // https://github.com/docker/cli/blob/master/cli/command/service/progress/progress.go
 func WaitOnService(ctx context.Context, cl *dockerClient.Client, serviceID, appName string) error {