diff --git a/WebService/Auth/AuthMiddleware.cs b/WebService/Auth/AuthMiddleware.cs
index a15445ff..22f6c1dc 100644
--- a/WebService/Auth/AuthMiddleware.cs
+++ b/WebService/Auth/AuthMiddleware.cs
@@ -53,6 +53,7 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
         private TokenValidationParameters tokenValidationParams;
         private readonly bool authRequired;
         private bool tokenValidationInitialized;
+        private DateTime tokenValidationExpiration;
 
         public AuthMiddleware(
             // ReSharper disable once UnusedParameter.Local
@@ -67,6 +68,7 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
             this.log = log;
             this.authRequired = config.AuthRequired;
             this.tokenValidationInitialized = false;
+            this.tokenValidationExpiration = DateTime.UtcNow;
 
             // This will show in development mode, or in case auth is turned off
             if (!this.authRequired)
@@ -83,7 +85,8 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
                     this.config.JwtIssuer,
                     this.config.JwtAudience,
                     this.config.JwtAllowedAlgos,
-                    this.config.JwtClockSkew
+                    this.config.JwtClockSkew,
+                    this.config.OpenIdTimeToLive
                 });
 
                 this.InitializeTokenValidationAsync(CancellationToken.None).Wait();
@@ -196,7 +199,8 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
 
         private async Task<bool> InitializeTokenValidationAsync(CancellationToken token)
         {
-            if (this.tokenValidationInitialized) return true;
+            // If the token has been initialized and is not past expiry, return.
+            if (this.tokenValidationInitialized && !this.TokenValidationExpired()) return true;
 
             try
             {
@@ -224,6 +228,7 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
                 };
 
                 this.tokenValidationInitialized = true;
+                this.tokenValidationExpiration = DateTime.UtcNow.Add(this.config.OpenIdTimeToLive);
             }
             catch (Exception e)
             {
@@ -232,5 +237,14 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
 
             return this.tokenValidationInitialized;
         }
+
+        /// <summary>
+        /// Checks if the OpenId Connect token has hit the expiration time.
+        /// </summary>
+        /// <returns>true if the token has expired</returns>
+        private bool TokenValidationExpired()
+        {
+            return this.tokenValidationExpiration > DateTime.UtcNow;
+        }
     }
 }
diff --git a/WebService/Auth/ClientAuthConfig.cs b/WebService/Auth/ClientAuthConfig.cs
index effeb221..68259d6f 100644
--- a/WebService/Auth/ClientAuthConfig.cs
+++ b/WebService/Auth/ClientAuthConfig.cs
@@ -36,6 +36,12 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
         // Clock skew allowed when validating tokens expiration
         // Default: 2 minutes
         TimeSpan JwtClockSkew { get; set; }
+
+        // Time to live for the OpenId Connect validation token.
+        // The metadata settings will expire so the token needs to be
+        // periodically recreated.
+        // Default: 7 days
+        TimeSpan OpenIdTimeToLive { get; set; }
     }
 
     public class ClientAuthConfig : IClientAuthConfig
@@ -49,5 +55,6 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Auth
         public string JwtIssuer { get; set; }
         public string JwtAudience { get; set; }
         public TimeSpan JwtClockSkew { get; set; }
+        public TimeSpan OpenIdTimeToLive { get; set; }
     }
 }
diff --git a/WebService/Runtime/Config.cs b/WebService/Runtime/Config.cs
index 8464205a..b9862133 100644
--- a/WebService/Runtime/Config.cs
+++ b/WebService/Runtime/Config.cs
@@ -92,6 +92,9 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Runtime
         private const string JWT_AUDIENCE_KEY = JWT_KEY + "audience";
         private const string JWT_CLOCK_SKEW_KEY = JWT_KEY + "clock_skew_seconds";
 
+        private const string OPEN_ID_KEY = APPLICATION_KEY + "ClientAuth:OpenIdConnect:";
+        private const string OPEN_ID_TTL_KEY = OPEN_ID_KEY + "timeToLiveDays";
+
         private const string DEPLOYMENT_KEY = APPLICATION_KEY + "Deployment:";
         private const string AZURE_SUBSCRIPTION_DOMAIN = DEPLOYMENT_KEY + "azure_subscription_domain";
         private const string AZURE_SUBSCRIPTION_ID = DEPLOYMENT_KEY + "azure_subscription_id";
@@ -161,6 +164,8 @@ namespace Microsoft.Azure.IoTSolutions.DeviceSimulation.WebService.Runtime
                 JwtAudience = configData.GetString(JWT_AUDIENCE_KEY, String.Empty),
                 // By default the allowed clock skew is 2 minutes
                 JwtClockSkew = TimeSpan.FromSeconds(configData.GetInt(JWT_CLOCK_SKEW_KEY, 120)),
+                // By default the time to live for the OpenId connect token is 7 days
+                OpenIdTimeToLive = TimeSpan.FromDays(configData.GetInt(OPEN_ID_TTL_KEY, 7))
             };
         }
 
diff --git a/WebService/WebService.csproj b/WebService/WebService.csproj
index 0156a5e3..31b46e00 100644
--- a/WebService/WebService.csproj
+++ b/WebService/WebService.csproj
@@ -36,7 +36,7 @@
     <PackageReference Include="Microsoft.AspNetCore" Version="2.0.1" />
     <PackageReference Include="Microsoft.AspNetCore.Mvc" Version="2.0.1" />
     <PackageReference Include="Microsoft.Extensions.Configuration.Ini" Version="2.0.0" />
-    <PackageReference Include="Microsoft.IdentityModel.Protocols.OpenIdConnect" Version="2.1.5" />
+    <PackageReference Include="Microsoft.IdentityModel.Protocols.OpenIdConnect" Version="5.4.0" />
   </ItemGroup>
   <ItemGroup>
     <ProjectReference Include="..\Services\Services.csproj" />
diff --git a/WebService/appsettings.ini b/WebService/appsettings.ini
index 75e87a53..316f826c 100644
--- a/WebService/appsettings.ini
+++ b/WebService/appsettings.ini
@@ -208,6 +208,11 @@ audience="${?PCS_AUTH_AUDIENCE}"
 # Default: 2 minutes
 clock_skew_seconds = 300
 
+[TelemetryService:ClientAuth:OpenIdConnect]
+; Time to live for the OpenId Connect validation token.
+; The metadata settings will expire so the token needs to be periodically recreated.
+; Default: 7 days
+timeToLiveDays = 7
 
 # For more information about ASP.NET logging see
 # https://docs.microsoft.com/aspnet/core/fundamentals/logging
diff --git a/scripts/docker/content/set_env.sh b/scripts/docker/content/set_env.sh
index 98fb41de..798cb09d 100644
--- a/scripts/docker/content/set_env.sh
+++ b/scripts/docker/content/set_env.sh
@@ -81,10 +81,14 @@ set_env_vars() {
     while test ${#} -gt 0
     do
         _key=$1
-        _value=$(_get_keyvault_secret $2)
-
-        # export in current shell
-        export $_key=$_value
+	
+        if [ -z "${!_key}" ]; then
+                _value=$(_get_keyvault_secret $2)
+                # export in current shell
+                export $_key=$_value
+        else
+            echo "Variable $_key already set."
+        fi
 
         shift
         shift