diff --git a/cli/cmd/serve.go b/cli/cmd/serve.go
index 5e681884..119c797e 100644
--- a/cli/cmd/serve.go
+++ b/cli/cmd/serve.go
@@ -49,9 +49,7 @@ func runServe(ctx context.Context, opts serveOpts) error {
 	p := proxy.NewContainerAPI()
 
 	containersv1.RegisterContainersServer(s, p)
-	cliv1.RegisterCliServer(s, &cliServer{
-		ctx,
-	})
+	cliv1.RegisterCliServer(s, &cliServer{})
 
 	go func() {
 		<-ctx.Done()
@@ -66,7 +64,6 @@ func runServe(ctx context.Context, opts serveOpts) error {
 }
 
 type cliServer struct {
-	ctx context.Context
 }
 
 func (cs *cliServer) Contexts(ctx context.Context, request *cliv1.ContextsRequest) (*cliv1.ContextsResponse, error) {
diff --git a/server/server.go b/server/server.go
index d3a050f8..8a1287b7 100644
--- a/server/server.go
+++ b/server/server.go
@@ -48,12 +48,12 @@ import (
 func New(ctx context.Context) *grpc.Server {
 	s := grpc.NewServer(
 		grpc.ChainUnaryInterceptor(
-			unaryMeta(ctx),
+			unaryServerInterceptor(ctx),
 			unary,
 		),
 		grpc.ChainStreamInterceptor(
 			grpc.StreamServerInterceptor(stream),
-			grpc.StreamServerInterceptor(streamMeta(ctx)),
+			grpc.StreamServerInterceptor(streamServerInterceptor(ctx)),
 		),
 	)
 	hs := health.NewServer()
@@ -77,9 +77,11 @@ func stream(srv interface{}, ss grpc.ServerStream, info *grpc.StreamServerInfo,
 	return grpc_prometheus.StreamServerInterceptor(srv, ss, info, handler)
 }
 
-func unaryMeta(clictx context.Context) func(ctx context.Context, req interface{}, info *grpc.UnaryServerInfo, handler grpc.UnaryHandler) (interface{}, error) {
+// unaryServerInterceptor configures the context and sends it to the next handler
+func unaryServerInterceptor(clictx context.Context) func(ctx context.Context, req interface{}, info *grpc.UnaryServerInfo, handler grpc.UnaryHandler) (interface{}, error) {
 	return func(ctx context.Context, req interface{}, info *grpc.UnaryServerInfo, handler grpc.UnaryHandler) (interface{}, error) {
-		configuredCtx, err := configureContext(ctx, clictx)
+		currentContext := getContext(ctx)
+		configuredCtx, err := configureContext(clictx, currentContext)
 		if err != nil {
 			return nil, err
 		}
@@ -88,50 +90,66 @@ func unaryMeta(clictx context.Context) func(ctx context.Context, req interface{}
 	}
 }
 
-func streamMeta(clictx context.Context) func(srv interface{}, ss grpc.ServerStream, info *grpc.StreamServerInfo, handler grpc.StreamHandler) error {
+// streamServerInterceptor configures the context and sends it to the next handler
+func streamServerInterceptor(clictx context.Context) func(srv interface{}, ss grpc.ServerStream, info *grpc.StreamServerInfo, handler grpc.StreamHandler) error {
 	return func(srv interface{}, ss grpc.ServerStream, info *grpc.StreamServerInfo, handler grpc.StreamHandler) error {
-		ctx, err := configureContext(ss.Context(), clictx)
+		currentContext := getContext(ss.Context())
+		ctx, err := configureContext(clictx, currentContext)
 		if err != nil {
 			return err
 		}
 
-		nss := newServerStream(ctx, ss)
-
-		return handler(srv, nss)
+		return handler(srv, newServerStream(ctx, ss))
 	}
 }
 
-// nolint: golint
-func configureContext(ctx context.Context, clictx context.Context) (context.Context, error) {
+// getContext returns the current context name sent in the request metadata, it
+// returns an empty string if there is no metadata
+// not present
+func getContext(ctx context.Context) string {
 	md, ok := metadata.FromIncomingContext(ctx)
 	if !ok {
-		return ctx, nil
+		return ""
 	}
 
 	key, ok := md[apicontext.Key]
 	if !ok {
-		return ctx, nil
+		return ""
 	}
 
 	if len(key) == 1 {
-		s := store.ContextStore(clictx)
-		ctx = store.WithContextStore(ctx, s)
-		ctx = apicontext.WithCurrentContext(ctx, key[0])
+		return key[0]
+	}
 
-		c, err := client.New(ctx)
-		if err != nil {
-			return nil, err
-		}
+	return ""
+}
 
-		ctx, err = proxy.WithClient(ctx, c)
-		if err != nil {
-			return nil, err
-		}
+// configureContext populates the request context with objects the client
+// needs: the context store and the api client
+func configureContext(ctx context.Context, currentContext string) (context.Context, error) {
+	s := store.ContextStore(ctx)
+	ctx = store.WithContextStore(ctx, s)
+	if currentContext != "" {
+		ctx = apicontext.WithCurrentContext(ctx, currentContext)
+	}
+
+	c, err := client.New(ctx)
+	if err != nil {
+		return nil, err
+	}
+
+	ctx, err = proxy.WithClient(ctx, c)
+	if err != nil {
+		return nil, err
 	}
 
 	return ctx, nil
 }
 
+// A gRPC server stream will only let you get its context but
+// there is no way to set a new (augmented context) to the next
+// handler (like we do for a unary request). We need to wrap the grpc.ServerSteam
+// to be able to set a new context that will be sent to the next stream interceptor.
 type contextServerStream struct {
 	s   grpc.ServerStream
 	ctx context.Context