diff --git a/pkg/server/service.go b/pkg/server/service.go
index f3b27416f..4a7983087 100644
--- a/pkg/server/service.go
+++ b/pkg/server/service.go
@@ -9,6 +9,9 @@ import (
 	"strings"
 	"time"
 
+	"google.golang.org/grpc/metadata"
+	"k8s.io/apimachinery/pkg/util/rand"
+
 	"github.com/flyteorg/flytestdlib/contextutils"
 	"github.com/flyteorg/flytestdlib/promutils/labeled"
 
@@ -77,7 +80,8 @@ func newGRPCServer(ctx context.Context, pluginRegistry *plugins.Registry, cfg *c
 	scope promutils.Scope, opts ...grpc.ServerOption) (*grpc.Server, error) {
 
 	logger.Infof(ctx, "Registering default middleware with blanket auth validation")
-	pluginRegistry.RegisterDefault(plugins.PluginIDUnaryServiceMiddleware, grpcmiddleware.ChainUnaryServer(auth.BlanketAuthorization, auth.ExecutionUserIdentifierInterceptor))
+	pluginRegistry.RegisterDefault(plugins.PluginIDUnaryServiceMiddleware, grpcmiddleware.ChainUnaryServer(
+		RequestIDInterceptor, auth.BlanketAuthorization, auth.ExecutionUserIdentifierInterceptor))
 
 	// Not yet implemented for streaming
 	var chainedUnaryInterceptors grpc.UnaryServerInterceptor
@@ -228,11 +232,50 @@ func newHTTPServer(ctx context.Context, cfg *config.ServerConfig, _ *authConfig.
 		return nil, errors.Wrap(err, "error registering signal service")
 	}
 
-	mux.Handle("/", gwmux)
+	mux.HandleFunc("/", func(w http.ResponseWriter, r *http.Request) {
+		ctx := GetOrGenerateRequestIDForRequest(r)
+		gwmux.ServeHTTP(w, r.WithContext(ctx))
+	})
 
 	return mux, nil
 }
 
+// RequestIDInterceptor is a server interceptor that sets the request id on the context for any incoming calls.
+func RequestIDInterceptor(ctx context.Context, req interface{}, _ *grpc.UnaryServerInfo, handler grpc.UnaryHandler) (interface{}, error) {
+	return handler(GetOrGenerateRequestIDForGRPC(ctx), req)
+}
+
+// GetOrGenerateRequestIDForGRPC returns a context with request id set from the context or from grpc metadata if it exists,
+// otherwise it generates a new one.
+func GetOrGenerateRequestIDForGRPC(ctx context.Context) context.Context {
+	if ctx.Value(contextutils.RequestIDKey) != nil {
+		return ctx
+	} else if md, exists := metadata.FromIncomingContext(ctx); exists && len(md.Get(contextutils.RequestIDKey.String())) > 0 {
+		return contextutils.WithRequestID(ctx, md.Get(contextutils.RequestIDKey.String())[0])
+	} else {
+		return contextutils.WithRequestID(ctx, generateRequestID())
+	}
+}
+
+// GetOrGenerateRequestIDForRequest returns a context with request id set from the context or from metadata if it exists,
+// otherwise it generates a new one.
+func GetOrGenerateRequestIDForRequest(req *http.Request) context.Context {
+	ctx := req.Context()
+	if ctx.Value(contextutils.RequestIDKey) != nil {
+		return ctx
+	} else if md, exists := metadata.FromIncomingContext(ctx); exists && len(md.Get(contextutils.RequestIDKey.String())) > 0 {
+		return contextutils.WithRequestID(ctx, md.Get(contextutils.RequestIDKey.String())[0])
+	} else if req.Header != nil && req.Header.Get(contextutils.RequestIDKey.String()) != "" {
+		return contextutils.WithRequestID(ctx, req.Header.Get(contextutils.RequestIDKey.String()))
+	} else {
+		return contextutils.WithRequestID(ctx, generateRequestID())
+	}
+}
+
+func generateRequestID() string {
+	return "a-" + rand.String(20)
+}
+
 func serveGatewayInsecure(ctx context.Context, pluginRegistry *plugins.Registry, cfg *config.ServerConfig,
 	authCfg *authConfig.Config, storageConfig *storage.Config,
 	additionalHandlers map[string]func(http.ResponseWriter, *http.Request), scope promutils.Scope) error {