diff --git a/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs b/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs
index 56209b6a7d..31569f02ac 100644
--- a/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs
+++ b/src/Core/Billing/Licenses/Extensions/LicenseExtensions.cs
@@ -116,23 +116,51 @@ public static class LicenseExtensions
 
 public static class OrganizationLicenseExtensions
 {
-    public static DateTime CalculateFreshExpirationDate(this Organization org, SubscriptionInfo subscriptionInfo)
+    public static DateTime CalculateFreshExpirationDate(this Organization org, SubscriptionInfo subscriptionInfo, DateTime issued)
     {
         if (subscriptionInfo?.Subscription == null)
         {
-            if (org.PlanType == PlanType.Custom && org.ExpirationDate.HasValue)
-            {
-                return org.ExpirationDate.Value;
-            }
-
-            return DateTime.UtcNow.AddDays(7);
+            return org.PlanType == PlanType.Custom && org.ExpirationDate.HasValue
+                ? org.ExpirationDate.Value
+                : issued.AddDays(7);
         }
 
-        var subscription = subscriptionInfo.Subscription;
-
-        if (subscription.TrialEndDate > DateTime.UtcNow)
+        if (subscriptionInfo.Subscription.TrialEndDate.HasValue &&
+                 subscriptionInfo.Subscription.TrialEndDate.Value > DateTime.UtcNow)
         {
-            return subscription.TrialEndDate.Value;
+            return subscriptionInfo.Subscription.TrialEndDate.Value;
+        }
+
+        if (org.ExpirationDate.HasValue && org.ExpirationDate.Value < DateTime.UtcNow)
+        {
+            // expired
+            return org.ExpirationDate.Value;
+        }
+
+        if (subscriptionInfo?.Subscription?.PeriodDuration != null &&
+                    subscriptionInfo.Subscription.PeriodDuration > TimeSpan.FromDays(180))
+        {
+            return subscriptionInfo.Subscription.PeriodEndDate.Value.AddDays(Core.Constants.OrganizationSelfHostSubscriptionGracePeriodDays);
+        }
+
+        return org.ExpirationDate.HasValue
+            ? org.ExpirationDate.Value.AddMonths(11)
+            : issued.AddYears(1);
+    }
+
+    public static DateTime CalculateFreshRefreshDate(this Organization org, SubscriptionInfo subscriptionInfo, DateTime? expirationDate, DateTime issued)
+    {
+        if (subscriptionInfo?.Subscription == null)
+        {
+            return org.PlanType == PlanType.Custom && org.ExpirationDate.HasValue
+                ? org.ExpirationDate.Value
+                : issued.AddDays(7);
+        }
+
+        if (subscriptionInfo.Subscription.TrialEndDate.HasValue &&
+                 subscriptionInfo.Subscription.TrialEndDate.Value > DateTime.UtcNow)
+        {
+            return subscriptionInfo.Subscription.TrialEndDate.Value;
         }
 
         if (org.ExpirationDate.HasValue && org.ExpirationDate.Value < DateTime.UtcNow)
@@ -140,66 +168,48 @@ public static class OrganizationLicenseExtensions
             return org.ExpirationDate.Value;
         }
 
-        if (subscription.PeriodEndDate.HasValue && subscription.PeriodDuration > TimeSpan.FromDays(180))
+        if (subscriptionInfo?.Subscription?.PeriodDuration != null &&
+                    subscriptionInfo.Subscription.PeriodDuration > TimeSpan.FromDays(180))
         {
-            return subscription.PeriodEndDate
-                .Value
-                .AddDays(Bit.Core.Constants.OrganizationSelfHostSubscriptionGracePeriodDays);
+            return DateTime.UtcNow.AddDays(30);
         }
 
-        return org.ExpirationDate?.AddMonths(11) ?? DateTime.UtcNow.AddYears(1);
-    }
-
-    public static DateTime CalculateFreshRefreshDate(this Organization org, SubscriptionInfo subscriptionInfo, DateTime expirationDate)
-    {
-        if (subscriptionInfo?.Subscription == null ||
-            subscriptionInfo.Subscription.TrialEndDate > DateTime.UtcNow ||
-            org.ExpirationDate < DateTime.UtcNow)
-        {
-            return expirationDate;
-        }
-
-        return subscriptionInfo.Subscription.PeriodDuration > TimeSpan.FromDays(180) ||
-            DateTime.UtcNow - expirationDate > TimeSpan.FromDays(30)
+        return !expirationDate.HasValue || DateTime.UtcNow - expirationDate.Value > TimeSpan.FromDays(30)
             ? DateTime.UtcNow.AddDays(30)
-            : expirationDate;
+            : expirationDate.Value;
     }
 
-    public static DateTime CalculateFreshExpirationDateWithoutGracePeriod(this Organization org, SubscriptionInfo subscriptionInfo, DateTime expirationDate)
-    {
-        if (subscriptionInfo?.Subscription is null)
-        {
-            return expirationDate;
-        }
-
-        var subscription = subscriptionInfo.Subscription;
-
-        if (subscription.TrialEndDate <= DateTime.UtcNow &&
-            org.ExpirationDate >= DateTime.UtcNow &&
-            subscription.PeriodEndDate.HasValue &&
-            subscription.PeriodDuration > TimeSpan.FromDays(180))
-        {
-            return subscription.PeriodEndDate.Value;
-        }
-
-        return expirationDate;
-    }
+    public static DateTime? CalculateFreshExpirationDateWithoutGracePeriod(this Organization org, SubscriptionInfo subscriptionInfo) =>
+        subscriptionInfo?.Subscription != null &&
+        (!subscriptionInfo.Subscription.TrialEndDate.HasValue || subscriptionInfo.Subscription.TrialEndDate.Value <= DateTime.UtcNow) &&
+        (!org.ExpirationDate.HasValue || org.ExpirationDate.Value >= DateTime.UtcNow) &&
+        subscriptionInfo.Subscription.PeriodDuration != null &&
+        subscriptionInfo.Subscription.PeriodDuration > TimeSpan.FromDays(180)
+            ? subscriptionInfo.Subscription.PeriodEndDate
+            : null;
 
     public static bool IsTrialing(this Organization org, SubscriptionInfo subscriptionInfo) =>
-        subscriptionInfo?.Subscription is null
+        subscriptionInfo?.Subscription == null
             ? org.PlanType != PlanType.Custom || !org.ExpirationDate.HasValue
-            : subscriptionInfo.Subscription.TrialEndDate > DateTime.UtcNow;
+            : subscriptionInfo.Subscription.TrialEndDate.HasValue && subscriptionInfo.Subscription.TrialEndDate.Value > DateTime.UtcNow;
 }
 
 public static class UserLicenseExtensions
 {
     public static DateTime? CalculateFreshExpirationDate(this User user, SubscriptionInfo subscriptionInfo) =>
-        subscriptionInfo?.UpcomingInvoice?.Date?.AddDays(7) ?? user.PremiumExpirationDate?.AddDays(7);
+        subscriptionInfo == null
+            ? user.PremiumExpirationDate?.AddDays(7)
+            : subscriptionInfo.UpcomingInvoice?.Date != null
+                ? subscriptionInfo.UpcomingInvoice.Date.Value.AddDays(7)
+                : user.PremiumExpirationDate?.AddDays(7);
 
     public static DateTime? CalculateFreshRefreshDate(this User user, SubscriptionInfo subscriptionInfo) =>
-        subscriptionInfo?.UpcomingInvoice?.Date ?? user.PremiumExpirationDate;
+        subscriptionInfo == null
+            ? user.PremiumExpirationDate?.Date
+            : subscriptionInfo?.UpcomingInvoice?.Date;
 
     public static bool IsTrialing(this User user, SubscriptionInfo subscriptionInfo) =>
-        (subscriptionInfo?.Subscription?.TrialEndDate.HasValue ?? false) &&
-        subscriptionInfo.Subscription.TrialEndDate.Value > DateTime.UtcNow;
+        subscriptionInfo != null &&
+            (subscriptionInfo?.Subscription?.TrialEndDate.HasValue ?? false) &&
+            subscriptionInfo.Subscription.TrialEndDate.Value > DateTime.UtcNow;
 }
diff --git a/src/Core/Billing/Licenses/Services/Implementations/OrganizationLicenseClaimsFactory.cs b/src/Core/Billing/Licenses/Services/Implementations/OrganizationLicenseClaimsFactory.cs
index abe6299f5f..4df71e418f 100644
--- a/src/Core/Billing/Licenses/Services/Implementations/OrganizationLicenseClaimsFactory.cs
+++ b/src/Core/Billing/Licenses/Services/Implementations/OrganizationLicenseClaimsFactory.cs
@@ -11,10 +11,11 @@ public class OrganizationLicenseClaimsFactory : ILicenseClaimsFactory<Organizati
 {
     public Task<List<Claim>> GenerateClaims(Organization entity, LicenseContext licenseContext)
     {
+        var issued = DateTime.UtcNow;
         var subscriptionInfo = licenseContext.SubscriptionInfo;
-        var expires = entity.CalculateFreshExpirationDate(subscriptionInfo);
-        var refresh = entity.CalculateFreshRefreshDate(subscriptionInfo, expires);
-        var expirationWithoutGracePeriod = entity.CalculateFreshExpirationDateWithoutGracePeriod(subscriptionInfo, expires);
+        var expires = entity.CalculateFreshExpirationDate(subscriptionInfo, issued);
+        var refresh = entity.CalculateFreshRefreshDate(subscriptionInfo, expires, issued);
+        var expirationWithoutGracePeriod = entity.CalculateFreshExpirationDateWithoutGracePeriod(subscriptionInfo);
         var trial = entity.IsTrialing(subscriptionInfo);
 
         var claims = new List<Claim>
@@ -49,12 +50,16 @@ public class OrganizationLicenseClaimsFactory : ILicenseClaimsFactory<Organizati
             new(nameof(OrganizationLicenseConstants.Issued), DateTime.UtcNow.ToString(CultureInfo.InvariantCulture)),
             new(nameof(OrganizationLicenseConstants.Expires), expires.ToString(CultureInfo.InvariantCulture)),
             new(nameof(OrganizationLicenseConstants.Refresh), refresh.ToString(CultureInfo.InvariantCulture)),
-            new(nameof(OrganizationLicenseConstants.ExpirationWithoutGracePeriod), expirationWithoutGracePeriod.ToString(CultureInfo.InvariantCulture)),
             new(nameof(OrganizationLicenseConstants.Trial), trial.ToString()),
             new(nameof(OrganizationLicenseConstants.UseAdminSponsoredFamilies), entity.UseAdminSponsoredFamilies.ToString()),
             new(nameof(OrganizationLicenseConstants.UseOrganizationDomains), entity.UseOrganizationDomains.ToString()),
         };
 
+        if (expirationWithoutGracePeriod.HasValue)
+        {
+            claims.Add(new(nameof(OrganizationLicenseConstants.ExpirationWithoutGracePeriod), expirationWithoutGracePeriod.Value.ToString(CultureInfo.InvariantCulture)));
+        }
+
         if (entity.Name is not null)
         {
             claims.Add(new(nameof(OrganizationLicenseConstants.Name), entity.Name));
diff --git a/src/Core/Models/Business/OrganizationLicense.cs b/src/Core/Models/Business/OrganizationLicense.cs
index 89e9912490..dddaac34d1 100644
--- a/src/Core/Models/Business/OrganizationLicense.cs
+++ b/src/Core/Models/Business/OrganizationLicense.cs
@@ -88,48 +88,10 @@ public class OrganizationLicense : BaseLicense
         AllowAdminAccessToAllCollectionItems = org.AllowAdminAccessToAllCollectionItems;
         //
 
-        if (subscriptionInfo?.Subscription == null)
-        {
-            if (org.PlanType == PlanType.Custom && org.ExpirationDate.HasValue)
-            {
-                Expires = Refresh = org.ExpirationDate.Value;
-                Trial = false;
-            }
-            else
-            {
-                Expires = Refresh = Issued.AddDays(7);
-                Trial = true;
-            }
-        }
-        else if (subscriptionInfo.Subscription.TrialEndDate.HasValue &&
-                 subscriptionInfo.Subscription.TrialEndDate.Value > DateTime.UtcNow)
-        {
-            Expires = Refresh = subscriptionInfo.Subscription.TrialEndDate.Value;
-            Trial = true;
-        }
-        else
-        {
-            if (org.ExpirationDate.HasValue && org.ExpirationDate.Value < DateTime.UtcNow)
-            {
-                // expired
-                Expires = Refresh = org.ExpirationDate.Value;
-            }
-            else if (subscriptionInfo?.Subscription?.PeriodDuration != null &&
-                     subscriptionInfo.Subscription.PeriodDuration > TimeSpan.FromDays(180))
-            {
-                Refresh = DateTime.UtcNow.AddDays(30);
-                Expires = subscriptionInfo.Subscription.PeriodEndDate?.AddDays(Constants
-                    .OrganizationSelfHostSubscriptionGracePeriodDays);
-                ExpirationWithoutGracePeriod = subscriptionInfo.Subscription.PeriodEndDate;
-            }
-            else
-            {
-                Expires = org.ExpirationDate.HasValue ? org.ExpirationDate.Value.AddMonths(11) : Issued.AddYears(1);
-                Refresh = DateTime.UtcNow - Expires > TimeSpan.FromDays(30) ? DateTime.UtcNow.AddDays(30) : Expires;
-            }
-
-            Trial = false;
-        }
+        Expires = org.CalculateFreshExpirationDate(subscriptionInfo, Issued);
+        Refresh = org.CalculateFreshRefreshDate(subscriptionInfo, Expires, Issued);
+        ExpirationWithoutGracePeriod = org.CalculateFreshExpirationDateWithoutGracePeriod(subscriptionInfo);
+        Trial = org.IsTrialing(subscriptionInfo);
 
         UseAdminSponsoredFamilies = org.UseAdminSponsoredFamilies;
         Hash = Convert.ToBase64String(ComputeHash());
@@ -247,7 +209,7 @@ public class OrganizationLicense : BaseLicense
 
     private bool ValidLicenseVersion
     {
-        get => Version is >= 1 and <= 16;
+        get => Version is >= 1 and <= CurrentLicenseFileVersion + 1;
     }
 
     public override byte[] GetDataBytes(bool forHash = false)
@@ -569,7 +531,7 @@ public class OrganizationLicense : BaseLicense
             * validation.
             */
 
-        if (valid && Version >= 16)
+        if (valid && Version >= CurrentLicenseFileVersion + 1)
         {
             valid = organization.UseOrganizationDomains;
         }
diff --git a/src/Core/Models/Business/UserLicense.cs b/src/Core/Models/Business/UserLicense.cs
index 3528835836..34933a9c9b 100644
--- a/src/Core/Models/Business/UserLicense.cs
+++ b/src/Core/Models/Business/UserLicense.cs
@@ -24,12 +24,9 @@ public class UserLicense : BaseLicense
         Premium = user.Premium;
         MaxStorageGb = user.MaxStorageGb;
         Issued = DateTime.UtcNow;
-        Expires = subscriptionInfo?.UpcomingInvoice?.Date != null ?
-            subscriptionInfo.UpcomingInvoice.Date.Value.AddDays(7) :
-            user.PremiumExpirationDate?.AddDays(7);
-        Refresh = subscriptionInfo?.UpcomingInvoice?.Date;
-        Trial = (subscriptionInfo?.Subscription?.TrialEndDate.HasValue ?? false) &&
-            subscriptionInfo.Subscription.TrialEndDate.Value > DateTime.UtcNow;
+        Expires = user.CalculateFreshExpirationDate(subscriptionInfo);
+        Refresh = user.CalculateFreshRefreshDate(subscriptionInfo);
+        Trial = user.IsTrialing(subscriptionInfo);
 
         Hash = Convert.ToBase64String(ComputeHash());
         Signature = Convert.ToBase64String(licenseService.SignLicense(this));
@@ -46,9 +43,9 @@ public class UserLicense : BaseLicense
         Premium = user.Premium;
         MaxStorageGb = user.MaxStorageGb;
         Issued = DateTime.UtcNow;
-        Expires = user.PremiumExpirationDate?.AddDays(7);
-        Refresh = user.PremiumExpirationDate?.Date;
-        Trial = false;
+        Expires = user.CalculateFreshExpirationDate(null);
+        Refresh = user.CalculateFreshRefreshDate(null);
+        Trial = user.IsTrialing(null);
 
         Hash = Convert.ToBase64String(ComputeHash());
         Signature = Convert.ToBase64String(licenseService.SignLicense(this));