diff --git a/CHANGELOG.md b/CHANGELOG.md
index de4d8c9b6..84f4cfd79 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,10 @@ When adding entries, please treat them as if they could end up in a release any
 
 Thank you!
 
+# 0.19.10
+
+-  Fix codegen bug where string literals containing both `$` and `"` generated code that failed to compile on Scala 2.12 
+
 # 0.19.9
 
 - Support `@structurePattern` targeting unions using `{label}` and `{value}` magic identifiers in [#1978](https://github.com/disneystreaming/smithy4s/pull/1978)
diff --git a/modules/codegen/src/smithy4s/codegen/internals/Renderer.scala b/modules/codegen/src/smithy4s/codegen/internals/Renderer.scala
index ad2ee518a..911487eec 100644
--- a/modules/codegen/src/smithy4s/codegen/internals/Renderer.scala
+++ b/modules/codegen/src/smithy4s/codegen/internals/Renderer.scala
@@ -28,6 +28,7 @@ import software.amazon.smithy.model.node.Node
 import software.amazon.smithy.model.node._
 import software.amazon.smithy.model.shapes.ShapeId
 
+import scala.annotation.nowarn
 import scala.jdk.CollectionConverters._
 
 import Line._
@@ -1968,7 +1969,7 @@ private[internals] class Renderer(compilationUnit: CompilationUnit) { self =>
   }
 
   private def escapeForStringLiteral(raw: String): String = {
-    val sb = new StringBuilder("\"")
+    val sb = new StringBuilder("")
     raw.foreach {
       case '\b'                      => sb.append("\\b")
       case '\t'                      => sb.append("\\t")
@@ -1980,7 +1981,6 @@ private[internals] class Renderer(compilationUnit: CompilationUnit) { self =>
       case c if c >= ' ' && c <= '~' => sb.append(c)
       case c                         => sb.append("\\u%04x".format(c.toInt))
     }
-    sb.append('"')
     sb.toString()
   }
 
@@ -1995,7 +1995,14 @@ private[internals] class Renderer(compilationUnit: CompilationUnit) { self =>
     // render any such strings as interpolated strings (even though that would
     // otherwise be unecessary) so that we can render "$" as "$$", which get
     // converted back to "$" during interpolation.
-    val escaped = if (str.contains('$')) s"s${str.replace("$", "$$")}" else str
+
+    // However when using interpolated strings, we cannot use normal escaping
+    // for double quotes as it is not supported by scala 2.12.
+    val escaped = if (str.contains('$')) {
+      @nowarn("msg=possible missing interpolator")
+      val replaced = str.replace("$", "$$").replace("\\\"", "${'\\\"'}")
+      s"""s"$replaced""""
+    } else s""""$str""""
 
     line"$escaped"
   }
diff --git a/modules/codegen/test/src/smithy4s/codegen/internals/RendererSpec.scala b/modules/codegen/test/src/smithy4s/codegen/internals/RendererSpec.scala
index 8b995a6cc..577abdb83 100644
--- a/modules/codegen/test/src/smithy4s/codegen/internals/RendererSpec.scala
+++ b/modules/codegen/test/src/smithy4s/codegen/internals/RendererSpec.scala
@@ -22,6 +22,8 @@ import software.amazon.smithy.model.Model
 import software.amazon.smithy.model.shapes.EnumShape
 import software.amazon.smithy.model.shapes.StructureShape
 
+import scala.annotation.nowarn
+
 final class RendererSpec extends munit.ScalaCheckSuite {
   import TestUtils._
 
@@ -456,6 +458,33 @@ final class RendererSpec extends munit.ScalaCheckSuite {
     )
   }
 
+  test(
+    "string literal containing $ and \" is rendered correctly"
+  ) {
+    val smithy = """
+                   |$version: "2.0"
+                   |
+                   |namespace smithy4s
+                   |
+                   |/// foo $ "
+                   |string MyString
+                   |""".stripMargin
+
+    val contents = generateScalaCode(smithy).values
+
+    @nowarn("msg=possible missing interpolator")
+    val expected =
+      """Hints.dynamic(ShapeId("smithy.api", "documentation"), smithy4s.Document.fromString(s"foo $$ ${'\"'}"))"""
+    assert(
+      contents.exists(
+        _.contains(
+          expected
+        )
+      )
+    )
+    assert(s"foo $$ ${'\"'}" == "foo $ \"")
+  }
+
   test(
     "string literal containing /* is rendered as a string with * escaped as &ast;"
   ) {