diff --git a/docs/custom_configuration/index.md b/docs/custom_configuration/index.md
index f44be6c6d..32dda6c64 100644
--- a/docs/custom_configuration/index.md
+++ b/docs/custom_configuration/index.md
@@ -14,7 +14,7 @@ Testcontainers supports various configurations to set up your test environment.
 | `host.override`             | `TESTCONTAINERS_HOST_OVERRIDE`             | The host that exposes Docker's ports.                                                                                     | -                           |
 | `docker.socket.override`    | `TESTCONTAINERS_DOCKER_SOCKET_OVERRIDE`    | The file path to the Docker daemon socket that is used by Ryuk (resource reaper).                                         | `/var/run/docker.sock`      |
 | `ryuk.disabled`             | `TESTCONTAINERS_RYUK_DISABLED`             | Disables Ryuk (resource reaper).                                                                                          | `false`                     |
-| `ryuk.container.privileged` | `TESTCONTAINERS_RYUK_CONTAINER_PRIVILEGED` | Runs Ryuk (resource reaper) in privileged mode.                                                                           | `false`                     |
+| `ryuk.container.privileged` | `TESTCONTAINERS_RYUK_CONTAINER_PRIVILEGED` | Runs Ryuk (resource reaper) in privileged mode.                                                                           | `true`                      |
 | `ryuk.container.image`      | `TESTCONTAINERS_RYUK_CONTAINER_IMAGE`      | The Ryuk (resource reaper) Docker image.                                                                                  | `testcontainers/ryuk:0.5.1` |
 | `hub.image.name.prefix`     | `TESTCONTAINERS_HUB_IMAGE_NAME_PREFIX`     | The name to use for substituting the Docker Hub registry part of the image name.                                          | -                           |
 | `wait.strategy.retries`     | `TESTCONTAINERS_WAIT_STRATEGY_RETRIES`     | The wait strategy retry count.                                                                                            | `infinite`                  |
diff --git a/src/Testcontainers/Builders/DockerDesktopEndpointAuthenticationProvider.cs b/src/Testcontainers/Builders/DockerDesktopEndpointAuthenticationProvider.cs
index c7eddad4a..f2363f89a 100644
--- a/src/Testcontainers/Builders/DockerDesktopEndpointAuthenticationProvider.cs
+++ b/src/Testcontainers/Builders/DockerDesktopEndpointAuthenticationProvider.cs
@@ -91,7 +91,7 @@ public bool GetRyukDisabled()
     }
 
     /// <inheritdoc />
-    public bool GetRyukContainerPrivileged()
+    public bool? GetRyukContainerPrivileged()
     {
       return false;
     }
diff --git a/src/Testcontainers/Builders/TestcontainersEndpointAuthenticationProvider.cs b/src/Testcontainers/Builders/TestcontainersEndpointAuthenticationProvider.cs
index 93a42976d..49cedf99c 100644
--- a/src/Testcontainers/Builders/TestcontainersEndpointAuthenticationProvider.cs
+++ b/src/Testcontainers/Builders/TestcontainersEndpointAuthenticationProvider.cs
@@ -118,7 +118,7 @@ public bool GetRyukDisabled()
     }
 
     /// <inheritdoc />
-    public bool GetRyukContainerPrivileged()
+    public bool? GetRyukContainerPrivileged()
     {
       return _customConfiguration.GetRyukContainerPrivileged();
     }
diff --git a/src/Testcontainers/Configurations/CustomConfiguration.cs b/src/Testcontainers/Configurations/CustomConfiguration.cs
index c757b7f26..8f2166844 100644
--- a/src/Testcontainers/Configurations/CustomConfiguration.cs
+++ b/src/Testcontainers/Configurations/CustomConfiguration.cs
@@ -79,9 +79,9 @@ protected virtual bool GetRyukDisabled(string propertyName)
       return GetPropertyValue<bool>(propertyName);
     }
 
-    protected virtual bool GetRyukContainerPrivileged(string propertyName)
+    protected virtual bool? GetRyukContainerPrivileged(string propertyName)
     {
-      return GetPropertyValue<bool>(propertyName);
+      return GetPropertyValue<bool?>(propertyName);
     }
 
     protected virtual IImage GetRyukContainerImage(string propertyName)
@@ -127,16 +127,18 @@ private T GetPropertyValue<T>(string propertyName)
     {
       var type = Nullable.GetUnderlyingType(typeof(T)) ?? typeof(T);
 
+      var isNullable = type != typeof(T);
+
       switch (Type.GetTypeCode(type))
       {
         case TypeCode.Boolean:
         {
-          return (T)(object)(_properties.TryGetValue(propertyName, out var propertyValue) && ("1".Equals(propertyValue, StringComparison.Ordinal) || (bool.TryParse(propertyValue, out var result) && result)));
+          return (T)(object)(_properties.TryGetValue(propertyName, out var propertyValue) && bool.TryParse(propertyValue, out var result) ? result : isNullable ? null : "1".Equals(propertyValue, StringComparison.Ordinal));
         }
 
         case TypeCode.UInt16:
         {
-          return (T)(object)(_properties.TryGetValue(propertyName, out var propertyValue) && ushort.TryParse(propertyValue, out var result) ? result : null);
+          return (T)(object)(_properties.TryGetValue(propertyName, out var propertyValue) && ushort.TryParse(propertyValue, out var result) ? result : isNullable ? null : 0);
         }
 
         case TypeCode.String:
diff --git a/src/Testcontainers/Configurations/EnvironmentConfiguration.cs b/src/Testcontainers/Configurations/EnvironmentConfiguration.cs
index 2d5706944..cdacdc50a 100644
--- a/src/Testcontainers/Configurations/EnvironmentConfiguration.cs
+++ b/src/Testcontainers/Configurations/EnvironmentConfiguration.cs
@@ -140,7 +140,7 @@ public bool GetRyukDisabled()
     }
 
     /// <inheritdoc />
-    public bool GetRyukContainerPrivileged()
+    public bool? GetRyukContainerPrivileged()
     {
       return GetRyukContainerPrivileged(RyukContainerPrivileged);
     }
diff --git a/src/Testcontainers/Configurations/ICustomConfiguration.cs b/src/Testcontainers/Configurations/ICustomConfiguration.cs
index 7f0b173c2..f0a205d8c 100644
--- a/src/Testcontainers/Configurations/ICustomConfiguration.cs
+++ b/src/Testcontainers/Configurations/ICustomConfiguration.cs
@@ -92,7 +92,8 @@ internal interface ICustomConfiguration
     /// </summary>
     /// <returns>The Ryuk container privileged custom configuration.</returns>
     /// <remarks>https://dotnet.testcontainers.org/custom_configuration/.</remarks>
-    bool GetRyukContainerPrivileged();
+    [CanBeNull]
+    bool? GetRyukContainerPrivileged();
 
     /// <summary>
     /// Gets the Ryuk container image custom configuration.
diff --git a/src/Testcontainers/Configurations/PropertiesFileConfiguration.cs b/src/Testcontainers/Configurations/PropertiesFileConfiguration.cs
index 7e303f33e..2870e5449 100644
--- a/src/Testcontainers/Configurations/PropertiesFileConfiguration.cs
+++ b/src/Testcontainers/Configurations/PropertiesFileConfiguration.cs
@@ -127,7 +127,7 @@ public bool GetRyukDisabled()
     }
 
     /// <inheritdoc />
-    public bool GetRyukContainerPrivileged()
+    public bool? GetRyukContainerPrivileged()
     {
       const string propertyName = "ryuk.container.privileged";
       return GetRyukContainerPrivileged(propertyName);
diff --git a/src/Testcontainers/Configurations/TestcontainersSettings.cs b/src/Testcontainers/Configurations/TestcontainersSettings.cs
index efb611a91..3f7e3d57f 100644
--- a/src/Testcontainers/Configurations/TestcontainersSettings.cs
+++ b/src/Testcontainers/Configurations/TestcontainersSettings.cs
@@ -67,7 +67,7 @@ static TestcontainersSettings()
     /// Gets or sets a value indicating whether the <see cref="ResourceReaper" /> privileged mode is enabled or not.
     /// </summary>
     public static bool ResourceReaperPrivilegedModeEnabled { get; set; }
-      = EnvironmentConfiguration.Instance.GetRyukContainerPrivileged() || PropertiesFileConfiguration.Instance.GetRyukContainerPrivileged();
+      = EnvironmentConfiguration.Instance.GetRyukContainerPrivileged() ?? PropertiesFileConfiguration.Instance.GetRyukContainerPrivileged() ?? true;
 
     /// <summary>
     /// Gets or sets the <see cref="ResourceReaper" /> image.
diff --git a/tests/Testcontainers.Tests/Unit/Configurations/CustomConfigurationTest.cs b/tests/Testcontainers.Tests/Unit/Configurations/CustomConfigurationTest.cs
index 260dfa067..6b4276cbc 100644
--- a/tests/Testcontainers.Tests/Unit/Configurations/CustomConfigurationTest.cs
+++ b/tests/Testcontainers.Tests/Unit/Configurations/CustomConfigurationTest.cs
@@ -159,11 +159,11 @@ public void GetRyukDisabledCustomConfiguration(string propertyName, string prope
       }
 
       [Theory]
-      [InlineData("", "", false)]
-      [InlineData("TESTCONTAINERS_RYUK_CONTAINER_PRIVILEGED", "", false)]
+      [InlineData("", "", null)]
+      [InlineData("TESTCONTAINERS_RYUK_CONTAINER_PRIVILEGED", "", null)]
       [InlineData("TESTCONTAINERS_RYUK_CONTAINER_PRIVILEGED", "false", false)]
       [InlineData("TESTCONTAINERS_RYUK_CONTAINER_PRIVILEGED", "true", true)]
-      public void GetRyukContainerPrivilegedCustomConfiguration(string propertyName, string propertyValue, bool expected)
+      public void GetRyukContainerPrivilegedCustomConfiguration(string propertyName, string propertyValue, bool? expected)
       {
         SetEnvironmentVariable(propertyName, propertyValue);
         ICustomConfiguration customConfiguration = new EnvironmentConfiguration();
@@ -362,11 +362,11 @@ public void GetRyukDisabledCustomConfiguration(string configuration, bool expect
       }
 
       [Theory]
-      [InlineData("", false)]
-      [InlineData("ryuk.container.privileged=", false)]
+      [InlineData("", null)]
+      [InlineData("ryuk.container.privileged=", null)]
       [InlineData("ryuk.container.privileged=false", false)]
       [InlineData("ryuk.container.privileged=true", true)]
-      public void GetRyukContainerPrivilegedCustomConfiguration(string configuration, bool expected)
+      public void GetRyukContainerPrivilegedCustomConfiguration(string configuration, bool? expected)
       {
         ICustomConfiguration customConfiguration = new PropertiesFileConfiguration(new[] { configuration });
         Assert.Equal(expected, customConfiguration.GetRyukContainerPrivileged());