diff --git a/smithy-kotlin-codegen/src/main/kotlin/software/amazon/smithy/kotlin/codegen/core/KotlinWriter.kt b/smithy-kotlin-codegen/src/main/kotlin/software/amazon/smithy/kotlin/codegen/core/KotlinWriter.kt
index 977426e39..e8bd1ea64 100644
--- a/smithy-kotlin-codegen/src/main/kotlin/software/amazon/smithy/kotlin/codegen/core/KotlinWriter.kt
+++ b/smithy-kotlin-codegen/src/main/kotlin/software/amazon/smithy/kotlin/codegen/core/KotlinWriter.kt
@@ -295,7 +295,7 @@ private val commonHtmlTags = setOf(
 // NOTE: Currently we look for specific strings of Html tags commonly found in docs
 //       and remove them.  A better solution would be to generally convert from HTML to "pure"
 //       markdown such that formatting is preserved.
-// TODO: https://www.pivotaltracker.com/story/show/177053427
+// TODO: https://github.com/awslabs/smithy-kotlin/issues/136
 private fun sanitizeDocumentation(doc: String): String = doc
     .stripAll(commonHtmlTags)
     // Docs can have valid $ characters that shouldn't run through formatters.
diff --git a/smithy-kotlin-codegen/src/main/kotlin/software/amazon/smithy/kotlin/codegen/lang/DocumentationPreprocessor.kt b/smithy-kotlin-codegen/src/main/kotlin/software/amazon/smithy/kotlin/codegen/lang/DocumentationPreprocessor.kt
new file mode 100644
index 000000000..295932ffb
--- /dev/null
+++ b/smithy-kotlin-codegen/src/main/kotlin/software/amazon/smithy/kotlin/codegen/lang/DocumentationPreprocessor.kt
@@ -0,0 +1,37 @@
+/*
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0.
+ */
+
+package software.amazon.smithy.kotlin.codegen.lang
+
+import software.amazon.smithy.kotlin.codegen.KotlinSettings
+import software.amazon.smithy.kotlin.codegen.integration.KotlinIntegration
+import software.amazon.smithy.model.Model
+import software.amazon.smithy.model.traits.DocumentationTrait
+import software.amazon.smithy.model.transform.ModelTransformer
+
+/**
+ * Sanitize all instances of [DocumentationTrait]
+ */
+class DocumentationPreprocessor : KotlinIntegration {
+
+    override fun preprocessModel(model: Model, settings: KotlinSettings): Model {
+        val transformer = ModelTransformer.create()
+        return transformer.mapTraits(model) { _, trait ->
+            when (trait) {
+                is DocumentationTrait -> {
+                    val docs = sanitize(trait.value)
+                    DocumentationTrait(docs, trait.sourceLocation)
+                }
+                else -> trait
+            }
+        }
+    }
+
+    // KDoc comments use inline markdown. Replace square brackets with escaped equivalents so that they
+    // are not rendered as invalid links
+    private fun sanitize(str: String): String =
+        str.replace("[", "[")
+            .replace("]", "]")
+}
diff --git a/smithy-kotlin-codegen/src/main/resources/META-INF/services/software.amazon.smithy.kotlin.codegen.integration.KotlinIntegration b/smithy-kotlin-codegen/src/main/resources/META-INF/services/software.amazon.smithy.kotlin.codegen.integration.KotlinIntegration
index 01d560c86..427dd7e30 100644
--- a/smithy-kotlin-codegen/src/main/resources/META-INF/services/software.amazon.smithy.kotlin.codegen.integration.KotlinIntegration
+++ b/smithy-kotlin-codegen/src/main/resources/META-INF/services/software.amazon.smithy.kotlin.codegen.integration.KotlinIntegration
@@ -1 +1,2 @@
 software.amazon.smithy.kotlin.codegen.lang.BuiltinPreprocessor
+software.amazon.smithy.kotlin.codegen.lang.DocumentationPreprocessor
diff --git a/smithy-kotlin-codegen/src/test/kotlin/software/amazon/smithy/kotlin/codegen/lang/DocumentationPreprocessorTest.kt b/smithy-kotlin-codegen/src/test/kotlin/software/amazon/smithy/kotlin/codegen/lang/DocumentationPreprocessorTest.kt
new file mode 100644
index 000000000..e5b5c8874
--- /dev/null
+++ b/smithy-kotlin-codegen/src/test/kotlin/software/amazon/smithy/kotlin/codegen/lang/DocumentationPreprocessorTest.kt
@@ -0,0 +1,71 @@
+/*
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0.
+ */
+
+package software.amazon.smithy.kotlin.codegen.lang
+
+import org.junit.jupiter.api.Test
+import software.amazon.smithy.kotlin.codegen.KotlinSettings
+import software.amazon.smithy.kotlin.codegen.model.expectTrait
+import software.amazon.smithy.kotlin.codegen.test.toSmithyModel
+import software.amazon.smithy.model.shapes.ShapeId
+import software.amazon.smithy.model.traits.DocumentationTrait
+import kotlin.test.assertEquals
+
+class DocumentationPreprocessorTest {
+    @Test
+    fun itEscapesSquareBrackets() {
+        // https://github.com/awslabs/aws-sdk-kotlin/issues/153
+        val model = """
+        namespace com.test
+        
+        service FooService {
+            version: "1.0.0"
+        }
+        
+        @documentation("This should not be modified")
+        structure Foo {
+            @documentation("member docs")
+            Unit: Unit,
+            Str: String
+        }
+        
+        @documentation("UserName@[SubDomain.]Domain.TopLevelDomain")
+        structure Unit {
+            Int: Integer
+        }
+        
+        union MyUnion {
+            @documentation("foo [bar [baz] qux] quux")
+            Integer: Integer,
+            String: String,
+            Unit: Unit
+        }
+        """.toSmithyModel()
+
+        val settings = KotlinSettings(
+            ShapeId.from("com.test#FooService"),
+            KotlinSettings.PackageSettings(
+                "test",
+                "1.0",
+                ""
+            ),
+            "Foo"
+        )
+
+        val integration = DocumentationPreprocessor()
+        val modified = integration.preprocessModel(model, settings)
+        val expectedDocs = listOf(
+            "com.test#Foo" to "This should not be modified",
+            "com.test#Foo\$Unit" to "member docs",
+            "com.test#Unit" to "UserName@[SubDomain.]Domain.TopLevelDomain",
+            "com.test#MyUnion\$Integer" to "foo [bar [baz] qux] quux",
+        )
+        expectedDocs.forEach { (shapeId, expected) ->
+            val shape = modified.expectShape(ShapeId.from(shapeId))
+            val docs = shape.expectTrait<DocumentationTrait>().value
+            assertEquals(expected, docs)
+        }
+    }
+}