diff --git a/cli/command/container/create.go b/cli/command/container/create.go
index 9f73b7f0afe3..00f187c36cf2 100644
--- a/cli/command/container/create.go
+++ b/cli/command/container/create.go
@@ -148,7 +148,7 @@ func pullImage(ctx context.Context, dockerCli command.Cli, img string, options *
 	if options.quiet {
 		out = streams.NewOut(io.Discard)
 	}
-	return jsonmessage.DisplayJSONMessagesToStream(responseBody, out, nil)
+	return jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, out, nil)
 }
 
 type cidFile struct {
diff --git a/cli/command/container/run_test.go b/cli/command/container/run_test.go
index 81b176d904c9..6c46aebd5de5 100644
--- a/cli/command/container/run_test.go
+++ b/cli/command/container/run_test.go
@@ -230,12 +230,7 @@ func TestRunPullTermination(t *testing.T) {
 		createContainerFunc: func(config *container.Config, hostConfig *container.HostConfig, networkingConfig *network.NetworkingConfig,
 			platform *specs.Platform, containerName string,
 		) (container.CreateResponse, error) {
-			select {
-			case <-ctx.Done():
-				return container.CreateResponse{}, ctx.Err()
-			default:
-			}
-			return container.CreateResponse{}, fakeNotFound{}
+			return container.CreateResponse{}, errors.New("shouldn't try to create a container")
 		},
 		containerAttachFunc: func(ctx context.Context, containerID string, options container.AttachOptions) (types.HijackedResponse, error) {
 			return types.HijackedResponse{}, errors.New("shouldn't try to attach to a container")
@@ -277,7 +272,7 @@ func TestRunPullTermination(t *testing.T) {
 	cmd := NewRunCommand(fakeCLI)
 	cmd.SetOut(io.Discard)
 	cmd.SetErr(io.Discard)
-	cmd.SetArgs([]string{"foobar:latest"})
+	cmd.SetArgs([]string{"--pull", "always", "foobar:latest"})
 
 	cmdErrC := make(chan error, 1)
 	go func() {
diff --git a/cli/command/image/build.go b/cli/command/image/build.go
index 4a258646dcce..d276b90b3bbd 100644
--- a/cli/command/image/build.go
+++ b/cli/command/image/build.go
@@ -361,7 +361,7 @@ func runBuild(ctx context.Context, dockerCli command.Cli, options buildOptions)
 		}
 	}
 
-	err = jsonmessage.DisplayJSONMessagesStream(response.Body, buildBuff, dockerCli.Out().FD(), dockerCli.Out().IsTerminal(), aux)
+	err = jsonmessage.DisplayJSONMessagesStream(ctx, response.Body, buildBuff, dockerCli.Out().FD(), dockerCli.Out().IsTerminal(), aux)
 	if err != nil {
 		if jerr, ok := err.(*jsonmessage.JSONError); ok {
 			// If no error code is set, default to 1
diff --git a/cli/command/image/import.go b/cli/command/image/import.go
index f6ad73d9baa4..3b979173ea70 100644
--- a/cli/command/image/import.go
+++ b/cli/command/image/import.go
@@ -90,5 +90,5 @@ func runImport(ctx context.Context, dockerCli command.Cli, options importOptions
 	}
 	defer responseBody.Close()
 
-	return jsonmessage.DisplayJSONMessagesToStream(responseBody, dockerCli.Out(), nil)
+	return jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, dockerCli.Out(), nil)
 }
diff --git a/cli/command/image/load.go b/cli/command/image/load.go
index 3dff2da082e6..7616a6bcfd69 100644
--- a/cli/command/image/load.go
+++ b/cli/command/image/load.go
@@ -89,7 +89,7 @@ func runLoad(ctx context.Context, dockerCli command.Cli, opts loadOptions) error
 	defer response.Body.Close()
 
 	if response.Body != nil && response.JSON {
-		return jsonmessage.DisplayJSONMessagesToStream(response.Body, dockerCli.Out(), nil)
+		return jsonmessage.DisplayJSONMessagesToStream(ctx, response.Body, dockerCli.Out(), nil)
 	}
 
 	_, err = io.Copy(dockerCli.Out(), response.Body)
diff --git a/cli/command/image/push.go b/cli/command/image/push.go
index 9ad2abd1ff87..d7d36a3f04c7 100644
--- a/cli/command/image/push.go
+++ b/cli/command/image/push.go
@@ -140,17 +140,17 @@ To push the complete multi-platform image, remove the --platform flag.
 	defer responseBody.Close()
 	if !opts.untrusted {
 		// TODO PushTrustedReference currently doesn't respect `--quiet`
-		return PushTrustedReference(dockerCli, repoInfo, ref, authConfig, responseBody)
+		return PushTrustedReference(ctx, dockerCli, repoInfo, ref, authConfig, responseBody)
 	}
 
 	if opts.quiet {
-		err = jsonmessage.DisplayJSONMessagesToStream(responseBody, streams.NewOut(io.Discard), handleAux(dockerCli))
+		err = jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, streams.NewOut(io.Discard), handleAux(dockerCli))
 		if err == nil {
 			fmt.Fprintln(dockerCli.Out(), ref.String())
 		}
 		return err
 	}
-	return jsonmessage.DisplayJSONMessagesToStream(responseBody, dockerCli.Out(), handleAux(dockerCli))
+	return jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, dockerCli.Out(), handleAux(dockerCli))
 }
 
 var notes []string
diff --git a/cli/command/image/trust.go b/cli/command/image/trust.go
index 6bb21fa556a7..c1ba94652563 100644
--- a/cli/command/image/trust.go
+++ b/cli/command/image/trust.go
@@ -39,13 +39,13 @@ func TrustedPush(ctx context.Context, cli command.Cli, repoInfo *registry.Reposi
 
 	defer responseBody.Close()
 
-	return PushTrustedReference(cli, repoInfo, ref, authConfig, responseBody)
+	return PushTrustedReference(ctx, cli, repoInfo, ref, authConfig, responseBody)
 }
 
 // PushTrustedReference pushes a canonical reference to the trust server.
 //
 //nolint:gocyclo
-func PushTrustedReference(ioStreams command.Streams, repoInfo *registry.RepositoryInfo, ref reference.Named, authConfig registrytypes.AuthConfig, in io.Reader) error {
+func PushTrustedReference(ctx context.Context, ioStreams command.Streams, repoInfo *registry.RepositoryInfo, ref reference.Named, authConfig registrytypes.AuthConfig, in io.Reader) error {
 	// If it is a trusted push we would like to find the target entry which match the
 	// tag provided in the function and then do an AddTarget later.
 	target := &client.Target{}
@@ -84,14 +84,14 @@ func PushTrustedReference(ioStreams command.Streams, repoInfo *registry.Reposito
 	default:
 		// We want trust signatures to always take an explicit tag,
 		// otherwise it will act as an untrusted push.
-		if err := jsonmessage.DisplayJSONMessagesToStream(in, ioStreams.Out(), nil); err != nil {
+		if err := jsonmessage.DisplayJSONMessagesToStream(ctx, in, ioStreams.Out(), nil); err != nil {
 			return err
 		}
 		fmt.Fprintln(ioStreams.Err(), "No tag specified, skipping trust metadata push")
 		return nil
 	}
 
-	if err := jsonmessage.DisplayJSONMessagesToStream(in, ioStreams.Out(), handleTarget); err != nil {
+	if err := jsonmessage.DisplayJSONMessagesToStream(ctx, in, ioStreams.Out(), handleTarget); err != nil {
 		return err
 	}
 
@@ -283,7 +283,7 @@ func imagePullPrivileged(ctx context.Context, cli command.Cli, imgRefAndAuth tru
 	if opts.quiet {
 		out = streams.NewOut(io.Discard)
 	}
-	return jsonmessage.DisplayJSONMessagesToStream(responseBody, out, nil)
+	return jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, out, nil)
 }
 
 // TrustedReference returns the canonical trusted reference for an image reference
diff --git a/cli/command/plugin/install.go b/cli/command/plugin/install.go
index 6d9ea7da5fda..6cee1cca337c 100644
--- a/cli/command/plugin/install.go
+++ b/cli/command/plugin/install.go
@@ -129,7 +129,7 @@ func runInstall(ctx context.Context, dockerCli command.Cli, opts pluginOptions)
 		return err
 	}
 	defer responseBody.Close()
-	if err := jsonmessage.DisplayJSONMessagesToStream(responseBody, dockerCli.Out(), nil); err != nil {
+	if err := jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, dockerCli.Out(), nil); err != nil {
 		return err
 	}
 	fmt.Fprintf(dockerCli.Out(), "Installed plugin %s\n", opts.remote) // todo: return proper values from the API for this result
diff --git a/cli/command/plugin/push.go b/cli/command/plugin/push.go
index 7f8b5dcca4e5..df99eb1ec687 100644
--- a/cli/command/plugin/push.go
+++ b/cli/command/plugin/push.go
@@ -66,8 +66,8 @@ func runPush(ctx context.Context, dockerCli command.Cli, opts pushOptions) error
 	defer responseBody.Close()
 
 	if !opts.untrusted {
-		return image.PushTrustedReference(dockerCli, repoInfo, named, authConfig, responseBody)
+		return image.PushTrustedReference(ctx, dockerCli, repoInfo, named, authConfig, responseBody)
 	}
 
-	return jsonmessage.DisplayJSONMessagesToStream(responseBody, dockerCli.Out(), nil)
+	return jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, dockerCli.Out(), nil)
 }
diff --git a/cli/command/plugin/upgrade.go b/cli/command/plugin/upgrade.go
index d609c8d01e31..8a571fe693aa 100644
--- a/cli/command/plugin/upgrade.go
+++ b/cli/command/plugin/upgrade.go
@@ -86,7 +86,7 @@ func runUpgrade(ctx context.Context, dockerCli command.Cli, opts pluginOptions)
 		return err
 	}
 	defer responseBody.Close()
-	if err := jsonmessage.DisplayJSONMessagesToStream(responseBody, dockerCli.Out(), nil); err != nil {
+	if err := jsonmessage.DisplayJSONMessagesToStream(ctx, responseBody, dockerCli.Out(), nil); err != nil {
 		return err
 	}
 	fmt.Fprintf(dockerCli.Out(), "Upgraded plugin %s to %s\n", opts.localName, opts.remote) // todo: return proper values from the API for this result
diff --git a/cli/command/service/helpers.go b/cli/command/service/helpers.go
index a8ff310a57f3..daac4a725a0f 100644
--- a/cli/command/service/helpers.go
+++ b/cli/command/service/helpers.go
@@ -24,7 +24,7 @@ func WaitOnService(ctx context.Context, dockerCli command.Cli, serviceID string,
 		return <-errChan
 	}
 
-	err := jsonmessage.DisplayJSONMessagesToStream(pipeReader, dockerCli.Out(), nil)
+	err := jsonmessage.DisplayJSONMessagesToStream(ctx, pipeReader, dockerCli.Out(), nil)
 	if err == nil {
 		err = <-errChan
 	}
diff --git a/cli/command/swarm/ca.go b/cli/command/swarm/ca.go
index 25c235a4503c..cd854c58ead2 100644
--- a/cli/command/swarm/ca.go
+++ b/cli/command/swarm/ca.go
@@ -120,7 +120,7 @@ func attach(ctx context.Context, dockerCli command.Cli, opts caOptions) error {
 		return <-errChan
 	}
 
-	err := jsonmessage.DisplayJSONMessagesToStream(pipeReader, dockerCli.Out(), nil)
+	err := jsonmessage.DisplayJSONMessagesToStream(ctx, pipeReader, dockerCli.Out(), nil)
 	if err == nil {
 		err = <-errChan
 	}