diff --git a/src/Api/Controllers/OrganizationsController.cs b/src/Api/Controllers/OrganizationsController.cs
index 36fdd2a99..ace46d438 100644
--- a/src/Api/Controllers/OrganizationsController.cs
+++ b/src/Api/Controllers/OrganizationsController.cs
@@ -50,6 +50,7 @@ public class OrganizationsController : Controller
     private readonly ICloudGetOrganizationLicenseQuery _cloudGetOrganizationLicenseQuery;
     private readonly IFeatureService _featureService;
     private readonly GlobalSettings _globalSettings;
+    private readonly ILicensingService _licensingService;
 
     public OrganizationsController(
         IOrganizationRepository organizationRepository,
@@ -69,7 +70,8 @@ public class OrganizationsController : Controller
         IUpdateOrganizationLicenseCommand updateOrganizationLicenseCommand,
         ICloudGetOrganizationLicenseQuery cloudGetOrganizationLicenseQuery,
         IFeatureService featureService,
-        GlobalSettings globalSettings)
+        GlobalSettings globalSettings,
+        ILicensingService licensingService)
     {
         _organizationRepository = organizationRepository;
         _organizationUserRepository = organizationUserRepository;
@@ -89,6 +91,7 @@ public class OrganizationsController : Controller
         _cloudGetOrganizationLicenseQuery = cloudGetOrganizationLicenseQuery;
         _featureService = featureService;
         _globalSettings = globalSettings;
+        _licensingService = licensingService;
     }
 
     [HttpGet("{id}")]
@@ -156,10 +159,14 @@ public class OrganizationsController : Controller
 
             return new OrganizationSubscriptionResponseModel(organization, subscriptionInfo, hideSensitiveData);
         }
-        else
+
+        if (_globalSettings.SelfHosted)
         {
-            return new OrganizationSubscriptionResponseModel(organization);
+            var orgLicense = await _licensingService.ReadOrganizationLicenseAsync(organization);
+            return new OrganizationSubscriptionResponseModel(organization, orgLicense);
         }
+
+        return new OrganizationSubscriptionResponseModel(organization);
     }
 
     [HttpGet("{id}/license")]
diff --git a/src/Api/Models/Response/Organizations/OrganizationResponseModel.cs b/src/Api/Models/Response/Organizations/OrganizationResponseModel.cs
index d2fdc1e0b..8b9d94d88 100644
--- a/src/Api/Models/Response/Organizations/OrganizationResponseModel.cs
+++ b/src/Api/Models/Response/Organizations/OrganizationResponseModel.cs
@@ -3,6 +3,7 @@ using Bit.Core.Enums;
 using Bit.Core.Models.Api;
 using Bit.Core.Models.Business;
 using Bit.Core.Utilities;
+using Constants = Bit.Core.Constants;
 
 namespace Bit.Api.Models.Response.Organizations;
 
@@ -108,9 +109,32 @@ public class OrganizationSubscriptionResponseModel : OrganizationResponseModel
         }
     }
 
+    public OrganizationSubscriptionResponseModel(Organization organization, OrganizationLicense license) :
+        this(organization)
+    {
+        if (license != null)
+        {
+            // License expiration should always include grace period - See OrganizationLicense.cs
+            Expiration = license.Expires;
+            // Use license.ExpirationWithoutGracePeriod if available, otherwise assume license expiration minus grace period
+            ExpirationWithoutGracePeriod = license.ExpirationWithoutGracePeriod ??
+                                             license.Expires?.AddDays(-Constants
+                                                 .OrganizationSelfHostSubscriptionGracePeriodDays);
+        }
+    }
+
     public string StorageName { get; set; }
     public double? StorageGb { get; set; }
     public BillingSubscription Subscription { get; set; }
     public BillingSubscriptionUpcomingInvoice UpcomingInvoice { get; set; }
+
+    /// <summary>
+    /// Date when a self-hosted organization's subscription expires, without any grace period.
+    /// </summary>
+    public DateTime? ExpirationWithoutGracePeriod { get; set; }
+
+    /// <summary>
+    /// Date when a self-hosted organization expires (includes grace period).
+    /// </summary>
     public DateTime? Expiration { get; set; }
 }
diff --git a/src/Core/Constants.cs b/src/Core/Constants.cs
index 8ae79084d..8ff378d00 100644
--- a/src/Core/Constants.cs
+++ b/src/Core/Constants.cs
@@ -13,6 +13,12 @@ public static class Constants
     public const long FileSize501mb = 501L * 1024L * 1024L;
     public const string DatabaseFieldProtectorPurpose = "DatabaseFieldProtection";
     public const string DatabaseFieldProtectedPrefix = "P|";
+
+    /// <summary>
+    /// Default number of days an organization has to apply an updated license to their self-hosted installation after
+    /// their subscription has expired.
+    /// </summary>
+    public const int OrganizationSelfHostSubscriptionGracePeriodDays = 60;
 }
 
 public static class TokenPurposes
diff --git a/src/Core/Models/Business/OrganizationLicense.cs b/src/Core/Models/Business/OrganizationLicense.cs
index 58cce4cff..c72430d94 100644
--- a/src/Core/Models/Business/OrganizationLicense.cs
+++ b/src/Core/Models/Business/OrganizationLicense.cs
@@ -78,7 +78,8 @@ public class OrganizationLicense : ILicense
                 subscriptionInfo.Subscription.PeriodDuration > TimeSpan.FromDays(180))
             {
                 Refresh = DateTime.UtcNow.AddDays(30);
-                Expires = subscriptionInfo?.Subscription.PeriodEndDate.Value.AddDays(60);
+                Expires = subscriptionInfo.Subscription.PeriodEndDate?.AddDays(Constants.OrganizationSelfHostSubscriptionGracePeriodDays);
+                ExpirationWithoutGracePeriod = subscriptionInfo.Subscription.PeriodEndDate;
             }
             else
             {
@@ -123,6 +124,7 @@ public class OrganizationLicense : ILicense
     public DateTime Issued { get; set; }
     public DateTime? Refresh { get; set; }
     public DateTime? Expires { get; set; }
+    public DateTime? ExpirationWithoutGracePeriod { get; set; }
     public bool Trial { get; set; }
     public LicenseType? LicenseType { get; set; }
     public string Hash { get; set; }
@@ -133,10 +135,12 @@ public class OrganizationLicense : ILicense
     /// <summary>
     /// Represents the current version of the license format. Should be updated whenever new fields are added.
     /// </summary>
-    private const int CURRENT_LICENSE_FILE_VERSION = 10;
+    /// <remarks>Intentionally set one version behind to allow self hosted users some time to update before
+    /// getting out of date license errors</remarks>
+    private const int CURRENT_LICENSE_FILE_VERSION = 11;
     private bool ValidLicenseVersion
     {
-        get => Version is >= 1 and <= 11;
+        get => Version is >= 1 and <= 12;
     }
 
     public byte[] GetDataBytes(bool forHash = false)
@@ -170,6 +174,8 @@ public class OrganizationLicense : ILicense
                     (Version >= 10 || !p.Name.Equals(nameof(UseScim))) &&
                     // UseCustomPermissions was added in Version 11
                     (Version >= 11 || !p.Name.Equals(nameof(UseCustomPermissions))) &&
+                    // ExpirationWithoutGracePeriod was added in Version 12
+                    (Version >= 12 || !p.Name.Equals(nameof(ExpirationWithoutGracePeriod))) &&
                     (
                         !forHash ||
                         (
diff --git a/test/Api.Test/Controllers/OrganizationsControllerTests.cs b/test/Api.Test/Controllers/OrganizationsControllerTests.cs
index aeadbb104..069b4bb27 100644
--- a/test/Api.Test/Controllers/OrganizationsControllerTests.cs
+++ b/test/Api.Test/Controllers/OrganizationsControllerTests.cs
@@ -40,6 +40,7 @@ public class OrganizationsControllerTests : IDisposable
     private readonly IUpdateOrganizationLicenseCommand _updateOrganizationLicenseCommand;
     private readonly IOrganizationDomainRepository _organizationDomainRepository;
     private readonly IFeatureService _featureService;
+    private readonly ILicensingService _licensingService;
 
     private readonly OrganizationsController _sut;
 
@@ -63,12 +64,13 @@ public class OrganizationsControllerTests : IDisposable
         _createOrganizationApiKeyCommand = Substitute.For<ICreateOrganizationApiKeyCommand>();
         _updateOrganizationLicenseCommand = Substitute.For<IUpdateOrganizationLicenseCommand>();
         _featureService = Substitute.For<IFeatureService>();
+        _licensingService = Substitute.For<ILicensingService>();
 
         _sut = new OrganizationsController(_organizationRepository, _organizationUserRepository,
             _policyRepository, _providerRepository, _organizationService, _userService, _paymentService, _currentContext,
             _ssoConfigRepository, _ssoConfigService, _getOrganizationApiKeyQuery, _rotateOrganizationApiKeyCommand,
             _createOrganizationApiKeyCommand, _organizationApiKeyRepository, _updateOrganizationLicenseCommand,
-            _cloudGetOrganizationLicenseQuery, _featureService, _globalSettings);
+            _cloudGetOrganizationLicenseQuery, _featureService, _globalSettings, _licensingService);
     }
 
     public void Dispose()