diff --git a/controllers/devworkspace/solver/che_routing_test.go b/controllers/devworkspace/solver/che_routing_test.go
index fb0f45f0c..4ff017192 100644
--- a/controllers/devworkspace/solver/che_routing_test.go
+++ b/controllers/devworkspace/solver/che_routing_test.go
@@ -1569,24 +1569,24 @@ func TestReportSubdomainExposedEndpointsLongUsername(t *testing.T) {
 	if e1.Name != "e1" {
 		t.Errorf("The first endpoint should have been e1 but is %s", e1.Name)
 	}
-	if e1.Url != "https://wsid-1.down.on.earth/1/" {
-		t.Errorf("The e1 endpoint should have the following URL: '%s' but has '%s'.", "https://wsid-1.down.on.earth/1/", e1.Url)
+	if e1.Url != "https://wsid-e1.down.on.earth/1/" {
+		t.Errorf("The e1 endpoint should have the following URL: '%s' but has '%s'.", "https://wsid-e1.down.on.earth/1/", e1.Url)
 	}
 
 	e2 := m1[1]
 	if e2.Name != "e2" {
 		t.Errorf("The second endpoint should have been e2 but is %s", e1.Name)
 	}
-	if e2.Url != "https://wsid-2.down.on.earth/2.js" {
-		t.Errorf("The e2 endpoint should have the following URL: '%s' but has '%s'.", "https://wsid-2.down.on.earth/2.js", e2.Url)
+	if e2.Url != "https://wsid-e2.down.on.earth/2.js" {
+		t.Errorf("The e2 endpoint should have the following URL: '%s' but has '%s'.", "https://wsid-e2.down.on.earth/2.js", e2.Url)
 	}
 
 	e3 := m1[2]
 	if e3.Name != "e3" {
 		t.Errorf("The third endpoint should have been e3 but is %s", e1.Name)
 	}
-	if e3.Url != "http://wsid-3.down.on.earth/" {
-		t.Errorf("The e3 endpoint should have the following URL: '%s' but has '%s'.", "https://wsid-3.down.on.earth/", e3.Url)
+	if e3.Url != "http://wsid-e3.down.on.earth/" {
+		t.Errorf("The e3 endpoint should have the following URL: '%s' but has '%s'.", "https://wsid-e3.down.on.earth/", e3.Url)
 	}
 }
 
diff --git a/controllers/devworkspace/solver/endpoint_strategy.go b/controllers/devworkspace/solver/endpoint_strategy.go
index 3d87af2b9..78e66517e 100644
--- a/controllers/devworkspace/solver/endpoint_strategy.go
+++ b/controllers/devworkspace/solver/endpoint_strategy.go
@@ -72,8 +72,10 @@ func (u UsernameWkspName) getEndpointPathPrefix(endpointPath string) string {
 func (u UsernameWkspName) getHostname(endpointInfo *EndpointInfo, baseDomain string) string {
 	subDomain := fmt.Sprintf("%s-%s-%s", u.username, u.workspaceName, endpointInfo.endpointName)
 	if errs := validation.IsValidLabelValue(subDomain); len(errs) > 0 {
-		// if subdomain is not valid, use legacy paths
-		return fmt.Sprintf("%s-%d.%s", u.workspaceID, endpointInfo.order, baseDomain)
+		// If subdomain is not valid (e.g. too long), use alternate format
+		// The below should always be under 63 characters, as endpoint names are limited to 15 characters and workspace IDs are
+		// 25 characters.
+		return fmt.Sprintf("%s-%s.%s", u.workspaceID, endpointInfo.endpointName, baseDomain)
 	}
 
 	return fmt.Sprintf("%s.%s", subDomain, baseDomain)