diff --git a/src/Umbraco.Web.UI/umbraco/config/lang/en.xml b/src/Umbraco.Web.UI/umbraco/config/lang/en.xml
index d99cd8f43f..22a97054e4 100644
--- a/src/Umbraco.Web.UI/umbraco/config/lang/en.xml
+++ b/src/Umbraco.Web.UI/umbraco/config/lang/en.xml
@@ -1474,8 +1474,10 @@ To manage your website, simply open the Umbraco back office and start adding con
 	  <key alias="xmlDataIntegrityCheckMedia">Media - Total XML: %0%, Total: %1%, Total invalid: %2%</key>
 	  <key alias="xmlDataIntegrityCheckContent">Content - Total XML: %0%, Total published: %1%, Total invalid: %2%</key>
 
-	  <key alias="httpsCheckValidCertificate">Your site certificate was marked as valid.</key>
+	  <key alias="httpsCheckValidCertificate">Your website's certificate is valid.</key>
 	  <key alias="httpsCheckInvalidCertificate">Certificate validation error: '%0%'</key>
+    <key alias="httpsCheckExpiredCertificate">Your website's SSL certificate has expired.</key>
+    <key alias="httpsCheckExpiringCertificate">Your website's SSL certificate is expiring in %0% days.</key>
 	  <key alias="httpsCheckInvalidUrl">Error pinging the URL %0% - '%1%'</key>
 	  <key alias="httpsCheckIsCurrentSchemeHttps">You are currently %0% viewing the site using the HTTPS scheme.</key>
 	  <key alias="httpsCheckConfigurationRectifyNotPossible">The appSetting 'umbracoUseSSL' is set to 'false' in your web.config file. Once you access this site using the HTTPS scheme, that should be set to 'true'.</key>
diff --git a/src/Umbraco.Web.UI/umbraco/config/lang/en_us.xml b/src/Umbraco.Web.UI/umbraco/config/lang/en_us.xml
index 63fc12101f..1847892530 100644
--- a/src/Umbraco.Web.UI/umbraco/config/lang/en_us.xml
+++ b/src/Umbraco.Web.UI/umbraco/config/lang/en_us.xml
@@ -1469,8 +1469,10 @@ To manage your website, simply open the Umbraco back office and start adding con
     <key alias="xmlDataIntegrityCheckMedia">Media - Total XML: %0%, Total: %1%, Total invalid: %2%</key>
     <key alias="xmlDataIntegrityCheckContent">Content - Total XML: %0%, Total published: %1%, Total invalid: %2%</key>
 
-    <key alias="httpsCheckValidCertificate">Your site certificate was marked as valid.</key>
+    <key alias="httpsCheckValidCertificate">Your website's certificate is valid.</key>
     <key alias="httpsCheckInvalidCertificate">Certificate validation error: '%0%'</key>
+    <key alias="httpsCheckExpiredCertificate">Your website's SSL certificate has expired.</key>
+    <key alias="httpsCheckExpiringCertificate">Your website's SSL certificate is expiring in %0% days.</key>   
     <key alias="httpsCheckInvalidUrl">Error pinging the URL %0% - '%1%'</key>
     <key alias="httpsCheckIsCurrentSchemeHttps">You are currently %0% viewing the site using the HTTPS scheme.</key>
     <key alias="httpsCheckConfigurationRectifyNotPossible">The appSetting 'umbracoUseSSL' is set to 'false' in your web.config file. Once you access this site using the HTTPS scheme, that should be set to 'true'.</key>
diff --git a/src/Umbraco.Web/HealthCheck/Checks/Security/HttpsCheck.cs b/src/Umbraco.Web/HealthCheck/Checks/Security/HttpsCheck.cs
index 4e2dc4f8f5..b50fc99a6e 100644
--- a/src/Umbraco.Web/HealthCheck/Checks/Security/HttpsCheck.cs
+++ b/src/Umbraco.Web/HealthCheck/Checks/Security/HttpsCheck.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using System.Net;
+using System.Security.Cryptography.X509Certificates;
 using System.Web;
 using Umbraco.Core.IO;
 using Umbraco.Core.Services;
@@ -53,7 +54,7 @@ namespace Umbraco.Web.HealthCheck.Checks.Security
         private HealthCheckStatus CheckForValidCertificate()
         {
             var message = string.Empty;
-            var success = false;
+            StatusResultType result;
             var url = HealthCheckContext.HttpContext.Request.Url;
 
             // Attempt to access the site over HTTPS to see if it HTTPS is supported 
@@ -65,7 +66,37 @@ namespace Umbraco.Web.HealthCheck.Checks.Security
             try
             {
                 var response = (HttpWebResponse)request.GetResponse();
-                success = response.StatusCode == HttpStatusCode.OK;
+                if (response.StatusCode == HttpStatusCode.OK)
+                {
+                    // Got a valid response, check now for if certificate expiring within 14 days
+                    // Hat-tip: https://stackoverflow.com/a/15343898/489433
+                    const int NumberOfDaysForExpiryWarning = 14;
+                    var cert = request.ServicePoint.Certificate;
+                    var cert2 = new X509Certificate2(cert);
+                    var expirationDate = cert2.NotAfter;
+
+                    var daysToExpiry = (int)Math.Floor((cert2.NotAfter - DateTime.Now).TotalDays);
+                    if (daysToExpiry <= 0)
+                    {
+                        result = StatusResultType.Error;
+                        message = _textService.Localize("healthcheck/httpsCheckExpiredCertificate");
+                    }
+                    else if (daysToExpiry < NumberOfDaysForExpiryWarning)
+                    {
+                        result = StatusResultType.Warning;
+                        message = _textService.Localize("healthcheck/httpsCheckExpiringCertificate", new[] { daysToExpiry.ToString() });
+                    }
+                    else
+                    {
+                        result = StatusResultType.Success;
+                        message = _textService.Localize("healthcheck/httpsCheckValidCertificate");
+                    }
+                }
+                else
+                {
+                    result = StatusResultType.Error;
+                    message = _textService.Localize("healthcheck/httpsCheckInvalidUrl", new[] { address, response.StatusDescription });
+                }
             }
             catch (Exception ex)
             {
@@ -80,17 +111,16 @@ namespace Umbraco.Web.HealthCheck.Checks.Security
                 {
                     message = _textService.Localize("healthcheck/httpsCheckInvalidUrl", new[] { address, ex.Message });
                 }
+
+                result = StatusResultType.Error;
             }
 
             var actions = new List<HealthCheckAction>();
 
-            if (success)
-                message = _textService.Localize("healthcheck/httpsCheckValidCertificate");
-
             return
                 new HealthCheckStatus(message)
                 {
-                    ResultType = success ? StatusResultType.Success : StatusResultType.Error,
+                    ResultType = result,
                     Actions = actions
                 };
         }