diff --git a/pkg/controller/proxyconfig/controller.go b/pkg/controller/proxyconfig/controller.go
index 8c7e7ec8e8..cffa010528 100644
--- a/pkg/controller/proxyconfig/controller.go
+++ b/pkg/controller/proxyconfig/controller.go
@@ -154,3 +154,9 @@ func isSpecHTTPSProxySet(proxyConfig *configv1.ProxySpec) bool {
 func isSpecNoProxySet(proxyConfig *configv1.ProxySpec) bool {
 	return len(proxyConfig.NoProxy) > 0
 }
+
+// isSpecReadinessEndpointsSet returns true if spec.readinessEndpoints of
+// proxyConfig is set.
+func isSpecReadinessEndpointsSet(proxyConfig *configv1.ProxySpec) bool {
+	return len(proxyConfig.ReadinessEndpoints) > 0
+}
diff --git a/pkg/controller/proxyconfig/validation.go b/pkg/controller/proxyconfig/validation.go
index a81d03b18a..855b09ec13 100644
--- a/pkg/controller/proxyconfig/validation.go
+++ b/pkg/controller/proxyconfig/validation.go
@@ -3,7 +3,10 @@ package proxyconfig
 import (
 	"fmt"
 	"net"
+	"net/http"
+	"net/url"
 	"strings"
+	"time"
 
 	configv1 "github.com/openshift/api/config/v1"
 	"github.com/openshift/cluster-network-operator/pkg/util/validation"
@@ -12,6 +15,11 @@ import (
 const (
 	proxyHTTPScheme  = "http"
 	proxyHTTPSScheme = "https"
+	// proxyProbeMaxRetries is the number of times to attempt an http GET
+	// to a readinessEndpoints endpoint.
+	proxyProbeMaxRetries = 3
+	// proxyProbeWaitTime is the time to wait before retrying a failed proxy probe.
+	proxyProbeWaitTime = 1 * time.Second
 	// noProxyWildcard is the string used to as a wildcard attached to a
 	// domain suffix in proxy.spec.noProxy to bypass proxying.
 	noProxyWildcard = "*"
@@ -52,5 +60,83 @@ func (r *ReconcileProxyConfig) ValidateProxyConfig(proxyConfig *configv1.ProxySp
 		}
 	}
 
+	if isSpecReadinessEndpointsSet(proxyConfig) {
+		for _, endpoint := range proxyConfig.ReadinessEndpoints {
+			scheme, err := validation.URI(endpoint)
+			if err != nil {
+				return fmt.Errorf("invalid URI for endpoint '%s': %v", endpoint, err)
+			}
+			switch {
+			case scheme == proxyHTTPScheme:
+				// TODO: Add case for proxyHTTPSScheme when CA support is merged.
+				if err := validateHTTPReadinessEndpoint(proxyConfig.HTTPProxy, endpoint); err != nil {
+					return fmt.Errorf("readinessEndpoint probe failed for endpoint '%s'", endpoint)
+				}
+			default:
+				// TODO: Update error to include proxyHTTPSScheme when CA support is merged.
+				return fmt.Errorf("readiness endpoints requires a '%s' URI sheme", proxyHTTPScheme)
+			}
+		}
+	}
+
 	return nil
 }
+
+// validateHTTPReadinessEndpoint validates an http readinessEndpoint endpoint.
+func validateHTTPReadinessEndpoint(httpProxy, endpoint string) error {
+	if err := validateHTTPReadinessEndpointWithRetries(httpProxy, endpoint, proxyProbeMaxRetries); err != nil {
+		return err
+	}
+
+	return nil
+}
+
+// validateHTTPReadinessEndpointWithRetries tries to validate an http
+// endpoint in a finite loop and returns the last result if it never succeeds.
+func validateHTTPReadinessEndpointWithRetries(httpProxy, endpoint string, retries int) error {
+	var err error
+	for i := 0; i < retries; i++ {
+		err = runHTTPReadinessProbe(httpProxy, endpoint)
+		if err == nil {
+			return nil
+		}
+		time.Sleep(proxyProbeWaitTime)
+	}
+
+	return err
+}
+
+// runHTTPReadinessProbe issues an http GET request to endpoint and returns
+// an error if a 2XX or 3XX http status code is not returned. The request
+// is proxied if proxy environment variables exist.
+func runHTTPReadinessProbe(httpProxy, endpoint string) error {
+	proxyURL, err := url.Parse(httpProxy)
+	if err != nil {
+		return fmt.Errorf("failed to parse httpProxy url '%s': %v", httpProxy, err)
+	}
+
+	transport := &http.Transport{
+		Proxy: http.ProxyURL(proxyURL),
+	}
+
+	client := &http.Client{
+		Transport: transport,
+	}
+
+	request, err := http.NewRequest("GET", endpoint, nil)
+	if err != nil {
+		return fmt.Errorf("failed to create http request for '%s': %v", endpoint, err)
+	}
+
+	resp, err := client.Do(request)
+	if err != nil {
+		return err
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode >= http.StatusOK && resp.StatusCode < http.StatusBadRequest {
+		return nil
+	}
+
+	return fmt.Errorf("http probe failed with statuscode: %d", resp.StatusCode)
+}