diff --git a/controllers/devworkspace/solver/che_routing.go b/controllers/devworkspace/solver/che_routing.go
index e22213619..5a0c16568 100644
--- a/controllers/devworkspace/solver/che_routing.go
+++ b/controllers/devworkspace/solver/che_routing.go
@@ -507,7 +507,9 @@ func provisionMainWorkspaceRoute(cheCluster *chev2.CheCluster, routing *dwo.DevW
 	}
 }
 
-// when accessing workspace url, if 5xx error is returned, redirect to the dashboard service
+// add5XXErrorHandling adds traefik middlewares to the traefik config such that
+// when a connection cannot be established with the workspace service (causing a 5XX error code), traefik
+// routes the request to the dashboard service instead.
 func add5XXErrorHandling(cfg *gateway.TraefikConfig, dwId string) {
 	// revalidate cache to prevent case where redirect to dashboard after trying to restart an idled workspace
 	noCacheHeader := map[string]string{"cache-control": "no-store, max-age=0"}
@@ -518,13 +520,16 @@ func add5XXErrorHandling(cfg *gateway.TraefikConfig, dwId string) {
 	cfg.AddErrors(dwId, "500-599", dashboardServiceName, "/")
 
 	if infrastructure.IsOpenShift() {
-		// On OpenShift, fire errors middleware after 4 seconds of not being able to connect to service
+		// If a connection cannot be established with the workspace service within the `DialTimeout`, traefik
+		// will retry the connection with an exponential backoff
 		cfg.HTTP.ServersTransports = map[string]*gateway.TraefikConfigServersTransport{}
+
 		cfg.HTTP.ServersTransports[dwId] = &gateway.TraefikConfigServersTransport{
 			ForwardingTimeouts: &gateway.TraefikConfigForwardingTimeouts{
-				DialTimeout: "4s",
+				DialTimeout: "2500ms",
 			},
 		}
+		cfg.AddRetry(dwId, 2, "500ms")
 		cfg.HTTP.Services[dwId].LoadBalancer.ServersTransport = dwId
 	}
 }
diff --git a/controllers/devworkspace/solver/che_routing_test.go b/controllers/devworkspace/solver/che_routing_test.go
index fc4783d4d..9e9d65196 100644
--- a/controllers/devworkspace/solver/che_routing_test.go
+++ b/controllers/devworkspace/solver/che_routing_test.go
@@ -402,7 +402,7 @@ func TestCreateRelocatedObjectsOpenshift(t *testing.T) {
 
 		workspaceMainConfig := gateway.TraefikConfig{}
 		assert.NoError(t, yaml.Unmarshal([]byte(traefikMainWorkspaceConfig), &workspaceMainConfig))
-		assert.Len(t, workspaceMainConfig.HTTP.Middlewares, 5)
+		assert.Len(t, workspaceMainConfig.HTTP.Middlewares, 6)
 
 		wsid = "wsid"
 		mwares := []string{
@@ -410,7 +410,8 @@ func TestCreateRelocatedObjectsOpenshift(t *testing.T) {
 			wsid + gateway.StripPrefixMiddlewareSuffix,
 			wsid + gateway.HeaderRewriteMiddlewareSuffix,
 			wsid + gateway.HeadersMiddlewareSuffix,
-			wsid + gateway.ErrorsMiddlewareSuffix}
+			wsid + gateway.ErrorsMiddlewareSuffix,
+			wsid + gateway.RetryMiddlewareSuffix}
 		for _, mware := range mwares {
 			assert.Contains(t, workspaceMainConfig.HTTP.Middlewares, mware)
 
diff --git a/pkg/deploy/gateway/traefik_config.go b/pkg/deploy/gateway/traefik_config.go
index d561fa039..b74ddf56a 100644
--- a/pkg/deploy/gateway/traefik_config.go
+++ b/pkg/deploy/gateway/traefik_config.go
@@ -39,6 +39,7 @@ type TraefikConfigMiddleware struct {
 	ForwardAuth *TraefikConfigForwardAuth `json:"forwardAuth,omitempty"`
 	Errors      *TraefikConfigErrors      `json:"errors,omitempty"`
 	Headers     *TraefikConfigHeaders     `json:"headers,omitempty"`
+	Retry       *TraefikConfigRetry       `json:"retry,omitempty"`
 	Plugin      *TraefikPlugin            `json:"plugin,omitempty"`
 }
 
@@ -75,6 +76,12 @@ type TraefikConfigHeaders struct {
 	CustomResponseHeaders map[string]string `json:"customResponseHeaders,omitempty"`
 }
 
+type TraefikConfigRetry struct {
+	CustomResponseHeaders map[string]string `json:"customResponseHeaders,omitempty"`
+	Attempts              int               `json:"attempts,omitempty"`
+	InitialInterval       string            `json:"initialInterval,omitempty"`
+}
+
 type TraefikPlugin struct {
 	HeaderRewrite *TraefikPluginHeaderRewrite `json:"header-rewrite,omitempty"`
 }
diff --git a/pkg/deploy/gateway/traefik_config_util.go b/pkg/deploy/gateway/traefik_config_util.go
index ad74c1c92..eef27c416 100644
--- a/pkg/deploy/gateway/traefik_config_util.go
+++ b/pkg/deploy/gateway/traefik_config_util.go
@@ -17,6 +17,7 @@ const (
 	AuthMiddlewareSuffix          = "-auth"
 	ErrorsMiddlewareSuffix        = "-errors"
 	HeadersMiddlewareSuffix       = "-headers"
+	RetryMiddlewareSuffix         = "-retry"
 )
 
 func CreateEmptyTraefikConfig() *TraefikConfig {
@@ -126,3 +127,14 @@ func (cfg *TraefikConfig) AddResponseHeaders(componentName string, headers map[s
 		},
 	}
 }
+
+func (cfg *TraefikConfig) AddRetry(componentName string, attempts int, initialInterval string) {
+	middlewareName := componentName + RetryMiddlewareSuffix
+	cfg.HTTP.Routers[componentName].Middlewares = append(cfg.HTTP.Routers[componentName].Middlewares, middlewareName)
+	cfg.HTTP.Middlewares[middlewareName] = &TraefikConfigMiddleware{
+		Retry: &TraefikConfigRetry{
+			Attempts:        attempts,
+			InitialInterval: initialInterval,
+		},
+	}
+}
diff --git a/pkg/deploy/gateway/traefik_config_util_test.go b/pkg/deploy/gateway/traefik_config_util_test.go
index 413ed4c20..fc6b39dcb 100644
--- a/pkg/deploy/gateway/traefik_config_util_test.go
+++ b/pkg/deploy/gateway/traefik_config_util_test.go
@@ -124,6 +124,22 @@ func TestAddResponseHeaders(t *testing.T) {
 	}
 }
 
+func TestAddRetry(t *testing.T) {
+	attempts := 3
+	initialInterval := "100ms"
+
+	cfg := CreateCommonTraefikConfig(testComponentName, testRule, 1, "http://svc:8080", []string{})
+	cfg.AddRetry(testComponentName, attempts, initialInterval)
+
+	assert.Len(t, cfg.HTTP.Routers[testComponentName].Middlewares, 1, *cfg)
+	assert.Len(t, cfg.HTTP.Middlewares, 1, *cfg)
+	middlewareName := cfg.HTTP.Routers[testComponentName].Middlewares[0]
+	if assert.Contains(t, cfg.HTTP.Middlewares, middlewareName, *cfg) && assert.NotNil(t, cfg.HTTP.Middlewares[middlewareName].Retry) {
+		assert.Equal(t, attempts, cfg.HTTP.Middlewares[middlewareName].Retry.Attempts)
+		assert.Equal(t, initialInterval, cfg.HTTP.Middlewares[middlewareName].Retry.InitialInterval)
+	}
+}
+
 func TestMiddlewaresPreserveOrder(t *testing.T) {
 	t.Run("strip-header", func(t *testing.T) {
 		cfg := CreateCommonTraefikConfig(testComponentName, testRule, 1, "http://svc:8080", []string{})