diff --git a/src/Core/Models/Api/Public/Request/MemberCreateRequestModel.cs b/src/Core/Models/Api/Public/Request/MemberCreateRequestModel.cs
index 5ebd3f866..a95d87deb 100644
--- a/src/Core/Models/Api/Public/Request/MemberCreateRequestModel.cs
+++ b/src/Core/Models/Api/Public/Request/MemberCreateRequestModel.cs
@@ -27,9 +27,9 @@ namespace Bit.Core.Models.Api.Public
                 yield return new ValidationResult($"Email is not valid.",
                     new string[] { nameof(Email) });
             }
-            else if (Email.Length > 50)
+            else if (Email.Length > 256)
             {
-                yield return new ValidationResult($"Email is longer than 50 characters.",
+                yield return new ValidationResult($"Email is longer than 256 characters.",
                     new string[] { nameof(Email) });
             }
         }
diff --git a/src/Core/Models/Api/Public/Request/OrganizationImportRequestModel.cs b/src/Core/Models/Api/Public/Request/OrganizationImportRequestModel.cs
index 45e140303..058b7be62 100644
--- a/src/Core/Models/Api/Public/Request/OrganizationImportRequestModel.cs
+++ b/src/Core/Models/Api/Public/Request/OrganizationImportRequestModel.cs
@@ -66,7 +66,7 @@ namespace Bit.Core.Models.Api.Public
             /// </summary>
             /// <example>jsmith@example.com</example>
             [EmailAddress]
-            [StringLength(50)]
+            [StringLength(256)]
             public string Email { get; set; }
             /// <summary>
             /// External identifier for reference or linking this member to another system, such as a user directory.
diff --git a/src/Core/Models/Api/Request/Accounts/DeleteRecoverRequestModel.cs b/src/Core/Models/Api/Request/Accounts/DeleteRecoverRequestModel.cs
index 39721eb25..f6d19ba7d 100644
--- a/src/Core/Models/Api/Request/Accounts/DeleteRecoverRequestModel.cs
+++ b/src/Core/Models/Api/Request/Accounts/DeleteRecoverRequestModel.cs
@@ -6,7 +6,7 @@ namespace Bit.Core.Models.Api
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string Email { get; set; }
     }
 }
diff --git a/src/Core/Models/Api/Request/Accounts/EmailRequestModel.cs b/src/Core/Models/Api/Request/Accounts/EmailRequestModel.cs
index ced59336a..f29324bf9 100644
--- a/src/Core/Models/Api/Request/Accounts/EmailRequestModel.cs
+++ b/src/Core/Models/Api/Request/Accounts/EmailRequestModel.cs
@@ -7,7 +7,7 @@ namespace Bit.Core.Models.Api
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string NewEmail { get; set; }
         [Required]
         [StringLength(300)]
diff --git a/src/Core/Models/Api/Request/Accounts/EmailTokenRequestModel.cs b/src/Core/Models/Api/Request/Accounts/EmailTokenRequestModel.cs
index c154bf9db..4dcd9608b 100644
--- a/src/Core/Models/Api/Request/Accounts/EmailTokenRequestModel.cs
+++ b/src/Core/Models/Api/Request/Accounts/EmailTokenRequestModel.cs
@@ -6,7 +6,7 @@ namespace Bit.Core.Models.Api
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string NewEmail { get; set; }
         [Required]
         [StringLength(300)]
diff --git a/src/Core/Models/Api/Request/Accounts/PasswordHintRequestModel.cs b/src/Core/Models/Api/Request/Accounts/PasswordHintRequestModel.cs
index 49b2fce30..b2b8f4c4a 100644
--- a/src/Core/Models/Api/Request/Accounts/PasswordHintRequestModel.cs
+++ b/src/Core/Models/Api/Request/Accounts/PasswordHintRequestModel.cs
@@ -6,7 +6,7 @@ namespace Bit.Core.Models.Api
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string Email { get; set; }
     }
 }
diff --git a/src/Core/Models/Api/Request/Accounts/PreloginRequestModel.cs b/src/Core/Models/Api/Request/Accounts/PreloginRequestModel.cs
index 7ac1386db..8dc260bf7 100644
--- a/src/Core/Models/Api/Request/Accounts/PreloginRequestModel.cs
+++ b/src/Core/Models/Api/Request/Accounts/PreloginRequestModel.cs
@@ -7,7 +7,7 @@ namespace Bit.Core.Models.Api
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string Email { get; set; }
     }
 }
diff --git a/src/Core/Models/Api/Request/Accounts/RegisterRequestModel.cs b/src/Core/Models/Api/Request/Accounts/RegisterRequestModel.cs
index c93c4c548..58a6db848 100644
--- a/src/Core/Models/Api/Request/Accounts/RegisterRequestModel.cs
+++ b/src/Core/Models/Api/Request/Accounts/RegisterRequestModel.cs
@@ -14,7 +14,7 @@ namespace Bit.Core.Models.Api
         public string Name { get; set; }
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string Email { get; set; }
         [Required]
         [StringLength(1000)]
diff --git a/src/Core/Models/Api/Request/EmergencyAccessRequstModels.cs b/src/Core/Models/Api/Request/EmergencyAccessRequstModels.cs
index c4a569621..e423a7a63 100644
--- a/src/Core/Models/Api/Request/EmergencyAccessRequstModels.cs
+++ b/src/Core/Models/Api/Request/EmergencyAccessRequstModels.cs
@@ -7,7 +7,7 @@ namespace Bit.Core.Models.Api.Request
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string Email { get; set; }
         [Required]
         public Enums.EmergencyAccessType? Type { get; set; }
diff --git a/src/Core/Models/Api/Request/InstallationRequestModel.cs b/src/Core/Models/Api/Request/InstallationRequestModel.cs
index 5b2728149..6fdfe7c75 100644
--- a/src/Core/Models/Api/Request/InstallationRequestModel.cs
+++ b/src/Core/Models/Api/Request/InstallationRequestModel.cs
@@ -7,7 +7,7 @@ namespace Bit.Core.Models.Api
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string Email { get; set; }
 
         public Installation ToInstallation()
diff --git a/src/Core/Models/Api/Request/Organizations/ImportOrganizationUsersRequestModel.cs b/src/Core/Models/Api/Request/Organizations/ImportOrganizationUsersRequestModel.cs
index 27d5280c8..7ac1db129 100644
--- a/src/Core/Models/Api/Request/Organizations/ImportOrganizationUsersRequestModel.cs
+++ b/src/Core/Models/Api/Request/Organizations/ImportOrganizationUsersRequestModel.cs
@@ -42,7 +42,7 @@ namespace Bit.Core.Models.Api
         public class User : IValidatableObject
         {
             [EmailAddress]
-            [StringLength(50)]
+            [StringLength(256)]
             public string Email { get; set; }
             public bool Deleted { get; set; }
             [Required]
diff --git a/src/Core/Models/Api/Request/Organizations/OrganizationCreateRequestModel.cs b/src/Core/Models/Api/Request/Organizations/OrganizationCreateRequestModel.cs
index af4eecbd2..e144d31c5 100644
--- a/src/Core/Models/Api/Request/Organizations/OrganizationCreateRequestModel.cs
+++ b/src/Core/Models/Api/Request/Organizations/OrganizationCreateRequestModel.cs
@@ -15,7 +15,7 @@ namespace Bit.Core.Models.Api
         [StringLength(50)]
         public string BusinessName { get; set; }
         [Required]
-        [StringLength(50)]
+        [StringLength(256)]
         [EmailAddress]
         public string BillingEmail { get; set; }
         public PlanType PlanType { get; set; }
diff --git a/src/Core/Models/Api/Request/Organizations/OrganizationUpdateRequestModel.cs b/src/Core/Models/Api/Request/Organizations/OrganizationUpdateRequestModel.cs
index 531a33d45..8e3dea662 100644
--- a/src/Core/Models/Api/Request/Organizations/OrganizationUpdateRequestModel.cs
+++ b/src/Core/Models/Api/Request/Organizations/OrganizationUpdateRequestModel.cs
@@ -16,7 +16,7 @@ namespace Bit.Core.Models.Api
         public string Identifier { get; set; }
         [EmailAddress]
         [Required]
-        [StringLength(50)]
+        [StringLength(256)]
         public string BillingEmail { get; set; }
 
         public Permissions Permissions { get; set; }
diff --git a/src/Core/Models/Api/Request/Organizations/OrganizationUserRequestModels.cs b/src/Core/Models/Api/Request/Organizations/OrganizationUserRequestModels.cs
index d57df816f..fa73209ad 100644
--- a/src/Core/Models/Api/Request/Organizations/OrganizationUserRequestModels.cs
+++ b/src/Core/Models/Api/Request/Organizations/OrganizationUserRequestModels.cs
@@ -38,9 +38,9 @@ namespace Bit.Core.Models.Api
                     yield return new ValidationResult($"Email #{i + 1} is not valid.",
                         new string[] { nameof(Emails) });
                 }
-                else if (email.Length > 50)
+                else if (email.Length > 256)
                 {
-                    yield return new ValidationResult($"Email #{i + 1} is longer than 50 characters.",
+                    yield return new ValidationResult($"Email #{i + 1} is longer than 256 characters.",
                         new string[] { nameof(Emails) });
                 }
             }
diff --git a/src/Core/Models/Api/Request/TwoFactorRequestModels.cs b/src/Core/Models/Api/Request/TwoFactorRequestModels.cs
index ad60e9dfc..e6bf6bacc 100644
--- a/src/Core/Models/Api/Request/TwoFactorRequestModels.cs
+++ b/src/Core/Models/Api/Request/TwoFactorRequestModels.cs
@@ -199,7 +199,7 @@ namespace Bit.Core.Models.Api
     {
         [Required]
         [EmailAddress]
-        [StringLength(50)]
+        [StringLength(256)]
         public string Email { get; set; }
 
         public User ToUser(User extistingUser)