diff --git a/pkg/libkubectl/apply_dynamic.go b/pkg/libkubectl/apply_dynamic.go
index a9c311d17b..0d0cdd912f 100644
--- a/pkg/libkubectl/apply_dynamic.go
+++ b/pkg/libkubectl/apply_dynamic.go
@@ -6,6 +6,7 @@ import (
 	"fmt"
 	"os"
 	"strings"
+	"time"
 
 	apierrors "k8s.io/apimachinery/pkg/api/errors"
 	"k8s.io/apimachinery/pkg/api/meta"
@@ -28,6 +29,12 @@ func (c *Client) ApplyDynamic(ctx context.Context, manifests []string) (string,
 		return "", fmt.Errorf("failed to create REST config: %w", err)
 	}
 
+	// Propagate context deadline to the HTTP client so discovery calls (which
+	// don't accept a context) still honour the caller's timeout.
+	if deadline, ok := ctx.Deadline(); ok {
+		restConfig.Timeout = time.Until(deadline)
+	}
+
 	// Create dynamic client
 	dynamicClient, err := dynamic.NewForConfig(restConfig)
 	if err != nil {
diff --git a/pkg/libstack/swarm/swarm.go b/pkg/libstack/swarm/swarm.go
index 617c7e92f3..b49b59b666 100644
--- a/pkg/libstack/swarm/swarm.go
+++ b/pkg/libstack/swarm/swarm.go
@@ -75,11 +75,15 @@ func NewSwarmDeployer() *SwarmDeployer { return &SwarmDeployer{} }
 
 // Deploy creates or updates a Docker Swarm stack from the given compose files.
 func (d *SwarmDeployer) Deploy(ctx context.Context, filePaths []string, options DeployOptions) error {
+	// WithCli replaces the context with Background internally, so we capture the
+	// caller's context here to preserve cancellation.
+	callerCtx := ctx
+
 	return libstack.WithCli(
 		ctx,
 		libstack.DockerCliOptions{Host: options.Host, Registries: options.Registries},
-		func(ctx context.Context, dockerCLI *command.DockerCli) error {
-			return deployStack(ctx, dockerCLI, filePaths, options)
+		func(_ context.Context, dockerCLI *command.DockerCli) error {
+			return deployStack(callerCtx, dockerCLI, filePaths, options)
 		})
 }
 
@@ -91,28 +95,32 @@ func (d *SwarmDeployer) Validate(_ context.Context, filePaths []string, options
 
 // Remove deletes all resources belonging to a Swarm stack and waits for tasks to terminate.
 func (d *SwarmDeployer) Remove(ctx context.Context, projectName string, options RemoveOptions) error {
+	// WithCli replaces the context with Background internally, so we capture the
+	// caller's context here to preserve cancellation.
+	callerCtx := ctx
+
 	return libstack.WithCli(
 		ctx,
 		libstack.DockerCliOptions{Host: options.Host, Registries: options.Registries},
-		func(ctx context.Context, dockerCLI *command.DockerCli) error {
+		func(_ context.Context, dockerCLI *command.DockerCli) error {
 			apiClient := dockerCLI.Client()
 
-			services, err := getStackServices(ctx, apiClient, projectName)
+			services, err := getStackServices(callerCtx, apiClient, projectName)
 			if err != nil {
 				return err
 			}
 
-			secrets, err := getStackSecrets(ctx, apiClient, projectName)
+			secrets, err := getStackSecrets(callerCtx, apiClient, projectName)
 			if err != nil {
 				return err
 			}
 
-			configs, err := getStackConfigs(ctx, apiClient, projectName)
+			configs, err := getStackConfigs(callerCtx, apiClient, projectName)
 			if err != nil {
 				return err
 			}
 
-			networks, err := getStackNetworks(ctx, apiClient, projectName)
+			networks, err := getStackNetworks(callerCtx, apiClient, projectName)
 			if err != nil {
 				return err
 			}
@@ -124,19 +132,19 @@ func (d *SwarmDeployer) Remove(ctx context.Context, projectName string, options
 
 			var errs []error
 
-			if err := removeServices(ctx, apiClient, services); err != nil {
+			if err := removeServices(callerCtx, apiClient, services); err != nil {
 				errs = append(errs, err)
 			}
 
-			if err := removeSecrets(ctx, apiClient, secrets); err != nil {
+			if err := removeSecrets(callerCtx, apiClient, secrets); err != nil {
 				errs = append(errs, err)
 			}
 
-			if err := removeConfigs(ctx, apiClient, configs); err != nil {
+			if err := removeConfigs(callerCtx, apiClient, configs); err != nil {
 				errs = append(errs, err)
 			}
 
-			if err := removeNetworks(ctx, apiClient, networks); err != nil {
+			if err := removeNetworks(callerCtx, apiClient, networks); err != nil {
 				errs = append(errs, err)
 			}
 
@@ -146,7 +154,7 @@ func (d *SwarmDeployer) Remove(ctx context.Context, projectName string, options
 
 			// Wait for all tasks to reach a terminal state before returning, mirroring
 			// the behaviour of `docker stack rm --detach=false`.
-			return waitOnTasks(ctx, apiClient, projectName)
+			return waitOnTasks(callerCtx, apiClient, projectName)
 		})
 }