diff --git a/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs b/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs
index 592df4e9d..b517a6ad8 100644
--- a/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs
+++ b/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs
@@ -100,6 +100,67 @@ public static class LicenseExtensions
             return default;
         }
 
-        return (T)Convert.ChangeType(claim.Value, typeof(T));
+        // Handle Guid
+        if (typeof(T) == typeof(Guid))
+        {
+            return Guid.TryParse(claim.Value, out var guid)
+                ? (T)(object)guid
+                : default;
+        }
+
+        // Handle DateTime
+        if (typeof(T) == typeof(DateTime))
+        {
+            return DateTime.TryParse(claim.Value, out var dateTime)
+                ? (T)(object)dateTime
+                : default;
+        }
+
+        // Handle TimeSpan
+        if (typeof(T) == typeof(TimeSpan))
+        {
+            return TimeSpan.TryParse(claim.Value, out var timeSpan)
+                ? (T)(object)timeSpan
+                : default;
+        }
+
+        // Check for Nullable Types
+        var underlyingType = Nullable.GetUnderlyingType(typeof(T)) ?? typeof(T);
+
+        // Handle Enums
+        if (underlyingType.IsEnum)
+        {
+            if (Enum.TryParse(underlyingType, claim.Value, true, out var enumValue))
+            {
+                return (T)enumValue; // Cast back to T
+            }
+
+            return default; // Return default value for non-nullable enums or null for nullable enums
+        }
+
+        // Handle other Nullable Types (e.g., int?, bool?)
+        if (underlyingType == typeof(int))
+        {
+            return int.TryParse(claim.Value, out var intValue)
+                ? (T)(object)intValue
+                : default;
+        }
+
+        if (underlyingType == typeof(bool))
+        {
+            return bool.TryParse(claim.Value, out var boolValue)
+                ? (T)(object)boolValue
+                : default;
+        }
+
+        if (underlyingType == typeof(double))
+        {
+            return double.TryParse(claim.Value, out var doubleValue)
+                ? (T)(object)doubleValue
+                : default;
+        }
+
+        // Fallback to Convert.ChangeType for other types including strings
+        return (T)Convert.ChangeType(claim.Value, underlyingType);
     }
 }
diff --git a/src/Core/Models/Business/OrganizationLicense.cs b/src/Core/Models/Business/OrganizationLicense.cs
index 42b4f8feb..36a275fbc 100644
--- a/src/Core/Models/Business/OrganizationLicense.cs
+++ b/src/Core/Models/Business/OrganizationLicense.cs
@@ -248,25 +248,27 @@ public class OrganizationLicense : ILicense
 
         var errorMessages = new StringBuilder();
 
-        var enabled = Token.ToClaimsPrincipal().GetValue<bool>(nameof(Enabled));
+        var claimsPrincipal = Token.ToClaimsPrincipal();
+
+        var enabled = claimsPrincipal.GetValue<bool>(nameof(Enabled));
         if (!enabled)
         {
             errorMessages.AppendLine("Your cloud-hosted organization is currently disabled.");
         }
 
-        var installationId = Token.ToClaimsPrincipal().GetValue<Guid>(nameof(InstallationId));
+        var installationId = claimsPrincipal.GetValue<Guid>(nameof(InstallationId));
         if (installationId != globalSettings.Installation.Id)
         {
             errorMessages.AppendLine("The installation ID does not match the current installation.");
         }
 
-        var selfHost = Token.ToClaimsPrincipal().GetValue<bool>(nameof(SelfHost));
+        var selfHost = claimsPrincipal.GetValue<bool>(nameof(SelfHost));
         if (!selfHost)
         {
             errorMessages.AppendLine("The license does not allow for on-premise hosting of organizations.");
         }
 
-        var licenseType = Token.ToClaimsPrincipal().GetValue<LicenseType>(nameof(LicenseType));
+        var licenseType = claimsPrincipal.GetValue<LicenseType>(nameof(LicenseType));
         if (licenseType != Enums.LicenseType.Organization)
         {
             errorMessages.AppendLine("Premium licenses cannot be applied to an organization. " +