diff --git a/Source/StrongGrid.IntegrationTests/Tests/Mail.cs b/Source/StrongGrid.IntegrationTests/Tests/Mail.cs
index b389b10b..ce625aeb 100644
--- a/Source/StrongGrid.IntegrationTests/Tests/Mail.cs
+++ b/Source/StrongGrid.IntegrationTests/Tests/Mail.cs
@@ -59,14 +59,7 @@ public async Task RunAsync(IBaseClient client, TextWriter log, CancellationToken
 			};
 			var mailSettings = new MailSettings
 			{
-				SandboxMode = new SandboxModeSettings
-				{
-					Enabled = true
-				},
-				BypassListManagement = new BypassListManagementSettings
-				{
-					Enabled = false
-				},
+				SandboxModeEnabled = true,
 				Footer = new FooterSettings
 				{
 					Enabled = true,
diff --git a/Source/StrongGrid/Models/BypassListManagementSettings.cs b/Source/StrongGrid/Models/BypassListManagementSettings.cs
deleted file mode 100644
index 79baf4fe..00000000
--- a/Source/StrongGrid/Models/BypassListManagementSettings.cs
+++ /dev/null
@@ -1,22 +0,0 @@
-using Newtonsoft.Json;
-
-namespace StrongGrid.Models
-{
-	/// <summary>
-	/// Allows you to bypass all unsubscribe groups and suppressions to ensure that the email is
-	/// delivered to every single recipient. This should only be used in emergencies when it is
-	/// absolutely necessary that every recipient receives your email. Ex: outage emails, or forgot
-	/// password emails.
-	/// </summary>
-	public class BypassListManagementSettings
-	{
-		/// <summary>
-		/// Gets or sets a value indicating whether this <see cref="BypassListManagementSettings"/> is enabled.
-		/// </summary>
-		/// <value>
-		///   <c>true</c> if enabled; otherwise, <c>false</c>.
-		/// </value>
-		[JsonProperty("enable", NullValueHandling = NullValueHandling.Ignore)]
-		public bool Enabled { get; set; }
-	}
-}
diff --git a/Source/StrongGrid/Models/EmailAddressSetting.cs b/Source/StrongGrid/Models/EmailAddressSetting.cs
index a3135ade..d03cf3bf 100644
--- a/Source/StrongGrid/Models/EmailAddressSetting.cs
+++ b/Source/StrongGrid/Models/EmailAddressSetting.cs
@@ -1,4 +1,4 @@
-using Newtonsoft.Json;
+using Newtonsoft.Json;
 
 namespace StrongGrid.Models
 {
@@ -13,7 +13,7 @@ public class EmailAddressSetting
 		/// <value>
 		///   <c>true</c> if enabled; otherwise, <c>false</c>.
 		/// </value>
-		[JsonProperty("enabled", NullValueHandling = NullValueHandling.Ignore)]
+		[JsonProperty("enabled")]
 		public bool Enabled { get; set; }
 
 		/// <summary>
@@ -22,7 +22,7 @@ public class EmailAddressSetting
 		/// <value>
 		/// The email address.
 		/// </value>
-		[JsonProperty("email", NullValueHandling = NullValueHandling.Ignore)]
+		[JsonProperty("email")]
 		public string EmailAddress { get; set; }
 	}
 }
diff --git a/Source/StrongGrid/Models/MailSettings.cs b/Source/StrongGrid/Models/MailSettings.cs
index 47890a81..bb08b5b4 100644
--- a/Source/StrongGrid/Models/MailSettings.cs
+++ b/Source/StrongGrid/Models/MailSettings.cs
@@ -1,5 +1,3 @@
-using Newtonsoft.Json;
-
 namespace StrongGrid.Models
 {
 	/// <summary>
@@ -8,30 +6,50 @@ namespace StrongGrid.Models
 	public class MailSettings
 	{
 		/// <summary>
-		/// Gets or sets the bypass list management.
+		/// Gets or sets a value indicating whether to bypass all unsubscribe groups and suppressions to ensure that the email is delivered to every single recipient.
+		/// This should only be used in emergencies when it is absolutely necessary that every recipient receives your email.
+		/// </summary>
+		/// <remarks>
+		/// This filter cannot be combined with any other bypass filters.
+		/// </remarks>
+		public bool BypassListManagement { get; set; } = false;
+
+		/// <summary>
+		/// Gets or sets a value indicating whether to bypass the spam report list to ensure that the email is delivered to recipients.
+		/// Bounce and unsubscribe lists will still be checked; addresses on these other lists will not receive the message.
+		/// </summary>
+		/// <remarks>
+		/// This filter cannot be combined with the <see cref="BypassListManagement">bypass_list_management filter</see>.
+		/// </remarks>
+		public bool BypassSpamManagement { get; set; } = false;
+
+		/// <summary>
+		/// Gets or sets a value indicating whether to bypass the bounce list to ensure that the email is delivered to recipients.
+		/// Spam report and unsubscribe lists will still be checked; addresses on these other lists will not receive the message.
+		/// </summary>
+		/// <remarks>
+		/// This filter cannot be combined with the <see cref="BypassListManagement">bypass_list_management filter</see>.
+		/// </remarks>
+		public bool BypassBounceManagement { get; set; } = false;
+
+		/// <summary>
+		/// Gets or sets a value indicating whether to bypass the global unsubscribe list to ensure that the email is delivered to recipients.
+		/// Bounce and spam report lists will still be checked; addresses on these other lists will not receive the message.
+		/// This filter applies only to global unsubscribes and will not bypass group unsubscribes.
 		/// </summary>
-		/// <value>
-		/// The bypass list management.
-		/// </value>
-		[JsonProperty("bypass_list_management", NullValueHandling = NullValueHandling.Ignore)]
-		public BypassListManagementSettings BypassListManagement { get; set; }
+		/// <remarks>
+		/// This filter cannot be combined with the <see cref="BypassListManagement">bypass_list_management filter</see>.
+		/// </remarks>
+		public bool BypassUnsubscribeManagement { get; set; } = false;
 
 		/// <summary>
 		/// Gets or sets the footer.
 		/// </summary>
-		/// <value>
-		/// The footer.
-		/// </value>
-		[JsonProperty("footer", NullValueHandling = NullValueHandling.Ignore)]
 		public FooterSettings Footer { get; set; }
 
 		/// <summary>
-		/// Gets or sets the sandbox mode.
+		/// Gets or sets a value indicating whether the sandbox mode is enabled or not.
 		/// </summary>
-		/// <value>
-		/// The sandbox mode.
-		/// </value>
-		[JsonProperty("sandbox_mode", NullValueHandling = NullValueHandling.Ignore)]
-		public SandboxModeSettings SandboxMode { get; set; }
+		public bool SandboxModeEnabled { get; set; } = false;
 	}
 }
diff --git a/Source/StrongGrid/Models/SandboxModeSettings.cs b/Source/StrongGrid/Models/SandboxModeSettings.cs
deleted file mode 100644
index 2b80eb39..00000000
--- a/Source/StrongGrid/Models/SandboxModeSettings.cs
+++ /dev/null
@@ -1,19 +0,0 @@
-using Newtonsoft.Json;
-
-namespace StrongGrid.Models
-{
-	/// <summary>
-	/// This allows you to send a test email to ensure that your request body is valid and formatted correctly.
-	/// </summary>
-	public class SandboxModeSettings
-	{
-		/// <summary>
-		/// Gets or sets a value indicating whether this <see cref="SandboxModeSettings"/> is enabled.
-		/// </summary>
-		/// <value>
-		///   <c>true</c> if enabled; otherwise, <c>false</c>.
-		/// </value>
-		[JsonProperty("enable", NullValueHandling = NullValueHandling.Ignore)]
-		public bool Enabled { get; set; }
-	}
-}
diff --git a/Source/StrongGrid/Resources/ISettings.cs b/Source/StrongGrid/Resources/ISettings.cs
index 7996f1de..aa8912d6 100644
--- a/Source/StrongGrid/Resources/ISettings.cs
+++ b/Source/StrongGrid/Resources/ISettings.cs
@@ -310,6 +310,7 @@ public interface ISettings
 		/// <returns>
 		/// The <see cref="SpamCheckingSettings" />.
 		/// </returns>
+		[Obsolete("As of august 2020, SendGrid has retired Spam Check mail settings.")]
 		Task<SpamCheckSettings> GetSpamCheckMailSettingsAsync(string onBehalfOf = null, CancellationToken cancellationToken = default);
 
 		/// <summary>
@@ -323,6 +324,7 @@ public interface ISettings
 		/// <returns>
 		/// The <see cref="SpamCheckingSettings" />.
 		/// </returns>
+		[Obsolete("As of august 2020, SendGrid has retired Spam Check mail settings.")]
 		Task<SpamCheckSettings> UpdateSpamCheckMailSettingsAsync(bool enabled, string postToUrl, int threshold, string onBehalfOf = null, CancellationToken cancellationToken = default);
 
 		/// <summary>
diff --git a/Source/StrongGrid/Resources/Mail.cs b/Source/StrongGrid/Resources/Mail.cs
index c0aa1bab..e43ef825 100644
--- a/Source/StrongGrid/Resources/Mail.cs
+++ b/Source/StrongGrid/Resources/Mail.cs
@@ -191,6 +191,16 @@ public async Task<string> SendAsync(
 			var isDynamicTemplate = Template.IsDynamic(templateId);
 			var personalizationConverter = new MailPersonalizationConverter(isDynamicTemplate);
 
+			// Manually serialize the MailSettings object because the shape of the C# class does not match the shape of the desired JSON.
+			// The C# class was intentionaly simplified to improve developers experience.
+			var mailSettingsJsonObject = new JObject();
+			mailSettingsJsonObject.AddPropertyIfValue("bypass_list_management/enable", mailSettings.BypassListManagement);
+			mailSettingsJsonObject.AddPropertyIfValue("bypass_spam_management/enable", mailSettings.BypassSpamManagement);
+			mailSettingsJsonObject.AddPropertyIfValue("bypass_bounce_management/enable", mailSettings.BypassBounceManagement);
+			mailSettingsJsonObject.AddPropertyIfValue("bypass_unsubscribe_management/enable", mailSettings.BypassUnsubscribeManagement);
+			mailSettingsJsonObject.AddPropertyIfValue("footer", mailSettings.Footer);
+			mailSettingsJsonObject.AddPropertyIfValue("sandbox_mode/enable", mailSettings.SandboxModeEnabled);
+
 			var data = new JObject();
 			data.AddPropertyIfValue("from", from);
 			data.AddPropertyIfValue("reply_to", replyTo);
@@ -203,7 +213,7 @@ public async Task<string> SendAsync(
 			data.AddPropertyIfValue("batch_id", batchId);
 			data.AddPropertyIfValue("asm", unsubscribeOptions);
 			data.AddPropertyIfValue("ip_pool_name", ipPoolName);
-			data.AddPropertyIfValue("mail_settings", mailSettings);
+			data.AddPropertyIfValue("mail_settings", mailSettingsJsonObject);
 			data.AddPropertyIfValue("tracking_settings", trackingSettings);
 			data.AddPropertyIfValue("personalizations", personalizationsCopy, personalizationConverter);