diff --git a/cli/command/plugin/install.go b/cli/command/plugin/install.go
index f1aa9d8725..6d9ea7da5f 100644
--- a/cli/command/plugin/install.go
+++ b/cli/command/plugin/install.go
@@ -136,13 +136,12 @@ func runInstall(ctx context.Context, dockerCli command.Cli, opts pluginOptions)
 	return nil
 }
 
-func acceptPrivileges(dockerCli command.Cli, name string) func(privileges types.PluginPrivileges) (bool, error) {
-	return func(privileges types.PluginPrivileges) (bool, error) {
+func acceptPrivileges(dockerCli command.Cli, name string) func(ctx context.Context, privileges types.PluginPrivileges) (bool, error) {
+	return func(ctx context.Context, privileges types.PluginPrivileges) (bool, error) {
 		fmt.Fprintf(dockerCli.Out(), "Plugin %q is requesting the following privileges:\n", name)
 		for _, privilege := range privileges {
 			fmt.Fprintf(dockerCli.Out(), " - %s: %v\n", privilege.Name, privilege.Value)
 		}
-		ctx := context.TODO()
 		return command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), "Do you grant the above permissions?")
 	}
 }
diff --git a/cli/command/registry.go b/cli/command/registry.go
index a1a499eee4..b365e5a8a7 100644
--- a/cli/command/registry.go
+++ b/cli/command/registry.go
@@ -2,6 +2,7 @@ package command
 
 import (
 	"bufio"
+	"context"
 	"fmt"
 	"io"
 	"os"
@@ -27,7 +28,7 @@ const patSuggest = "You can log in with your password or a Personal Access " +
 // RegistryAuthenticationPrivilegedFunc returns a RequestPrivilegeFunc from the specified registry index info
 // for the given command.
 func RegistryAuthenticationPrivilegedFunc(cli Cli, index *registrytypes.IndexInfo, cmdName string) types.RequestPrivilegeFunc {
-	return func() (string, error) {
+	return func(ctx context.Context) (string, error) {
 		fmt.Fprintf(cli.Out(), "\nPlease login prior to %s:\n", cmdName)
 		indexServer := registry.GetAuthConfigKey(index)
 		isDefaultRegistry := indexServer == registry.IndexServer
@@ -35,6 +36,13 @@ func RegistryAuthenticationPrivilegedFunc(cli Cli, index *registrytypes.IndexInf
 		if err != nil {
 			fmt.Fprintf(cli.Err(), "Unable to retrieve stored credentials for %s, error: %s.\n", indexServer, err)
 		}
+
+		select {
+		case <-ctx.Done():
+			return "", ctx.Err()
+		default:
+		}
+
 		err = ConfigureAuth(cli, "", "", &authConfig, isDefaultRegistry)
 		if err != nil {
 			return "", err