diff --git a/config/config.go b/config/config.go
index d146d4efa..70d82f6e6 100644
--- a/config/config.go
+++ b/config/config.go
@@ -448,6 +448,31 @@ func GetAllPrefixes() []ConfigPrefix {
 	return prefixes
 }
 
+// Helper function to start a metadata request.
+//
+// We see periodic timeouts when doing metadata lookup at sites.
+// Adding a modest retry will, hopefully, reduce the number of errors
+// that propagate out to users
+func startMetadataQuery(ctx context.Context, httpClient *http.Client, discoveryUrl *url.URL) (result *http.Response, err error) {
+	req, err := http.NewRequestWithContext(ctx, http.MethodGet, discoveryUrl.String(), nil)
+	if err != nil {
+		err = errors.Wrapf(err, "Failure when doing federation metadata request creation for %s", discoveryUrl)
+		return
+	}
+	req.Header.Set("User-Agent", "pelican/"+version)
+
+	result, err = httpClient.Do(req)
+	if err != nil {
+		var netErr net.Error
+		if errors.As(err, &netErr) && netErr.Timeout() {
+			err = MetadataTimeoutErr.Wrap(err)
+		} else {
+			err = NewMetadataError(err, "Error occurred when querying for metadata")
+		}
+	}
+	return
+}
+
 // This function is for discovering federations as specified by a url during a pelican:// transfer.
 // this does not populate global fields and is more temporary per url
 func DiscoverUrlFederation(ctx context.Context, federationDiscoveryUrl string) (metadata FederationDiscovery, err error) {
@@ -478,24 +503,23 @@ func DiscoverUrlFederation(ctx context.Context, federationDiscoveryUrl string) (
 		Transport: GetTransport(),
 		Timeout:   time.Second * 5,
 	}
-	req, err := http.NewRequestWithContext(ctx, http.MethodGet, discoveryUrl.String(), nil)
-	if err != nil {
-		err = errors.Wrapf(err, "Failure when doing federation metadata request creation for %s", discoveryUrl)
-		return
-	}
-	req.Header.Set("User-Agent", "pelican/"+version)
 
-	result, err := httpClient.Do(req)
-	if err != nil {
-		var netErr net.Error
-		if errors.As(err, &netErr) && netErr.Timeout() {
-			err = MetadataTimeoutErr.Wrap(err)
-			return
+	var result *http.Response
+	for idx := 1; idx <= 3; idx++ {
+		result, err = startMetadataQuery(ctx, &httpClient, discoveryUrl)
+		if err == nil {
+			break
+		} else if errors.Is(err, MetadataTimeoutErr) && ctx.Err() == nil {
+			log.Warningln("Timeout occurred when querying discovery URL", discoveryUrl.String(), "for metadata;", 3-idx, "retries remaining")
+			time.Sleep(2 * time.Second)
 		} else {
-			err = NewMetadataError(err, "Error occurred when querying for metadata")
 			return
 		}
 	}
+	if errors.Is(err, MetadataTimeoutErr) {
+		log.Errorln("3 timeouts occurred when querying discovery URL", discoveryUrl.String())
+		return
+	}
 
 	if result.Body != nil {
 		defer result.Body.Close()
diff --git a/config/config_test.go b/config/config_test.go
index 184d44eef..f3e441117 100644
--- a/config/config_test.go
+++ b/config/config_test.go
@@ -33,6 +33,7 @@ import (
 
 	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
+	log "github.com/sirupsen/logrus"
 	"github.com/sirupsen/logrus/hooks/test"
 	"github.com/spf13/viper"
 	"github.com/stretchr/testify/assert"
@@ -835,6 +836,49 @@ func TestDiscoverUrlFederation(t *testing.T) {
 		viper.Reset()
 	})
 
+	t.Run("TestMetadataDiscoveryTimeoutRetry", func(t *testing.T) {
+		viper.Set("tlsskipverify", true)
+		viper.Set("Logging.Level", "Debug")
+		viper.Set("Transport.ResponseHeaderTimeout", "300ms")
+		InitConfig()
+		err := InitClient()
+		require.NoError(t, err)
+
+		hook := test.NewGlobal()
+		logrus.SetLevel(logrus.WarnLevel)
+
+		// Create a server that sleeps for a longer duration than the timeout
+		ctr := 0
+		server := httptest.NewTLSServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			if ctr < 1 {
+				time.Sleep(2 * time.Second)
+			}
+
+			ctr += 1
+			w.WriteHeader(200)
+			_, err := w.Write([]byte("{\"director_endpoint\": \"https://osdf-director.osg-htc.org\", \"namespace_registration_endpoint\": \"https://osdf-registry.osg-htc.org\", \"jwks_uri\": \"https://osg-htc.org/osdf/public_signing_key.jwks\"}"))
+			assert.NoError(t, err)
+		}))
+		defer server.Close()
+
+		// Set a short timeout for the test
+		timeout := 5 * time.Second
+
+		// Create a context with the timeout
+		ctx, cancel := context.WithTimeout(context.Background(), timeout)
+		defer cancel()
+
+		// Call the function with the server URL and the context
+		_, err = DiscoverUrlFederation(ctx, server.URL)
+
+		assert.Equal(t, log.WarnLevel, hook.LastEntry().Level)
+		assert.Equal(t, "Timeout occurred when querying discovery URL "+server.URL+"/.well-known/pelican-configuration for metadata; 2 retries remaining", hook.LastEntry().Message)
+
+		// Assert that the error is the expected metadata timeout error
+		assert.NoError(t, err)
+		viper.Reset()
+	})
+
 	t.Run("TestCanceledContext", func(t *testing.T) {
 		// Create a server that waits for the context to be canceled
 		server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {