diff --git a/src/main/scala/higherkindness/rules_scala/workers/common/AnnexScalaInstance.scala b/src/main/scala/higherkindness/rules_scala/workers/common/AnnexScalaInstance.scala
index 4d3af8e4..60cbd3cf 100644
--- a/src/main/scala/higherkindness/rules_scala/workers/common/AnnexScalaInstance.scala
+++ b/src/main/scala/higherkindness/rules_scala/workers/common/AnnexScalaInstance.scala
@@ -7,7 +7,7 @@ import java.net.URLClassLoader
 import java.nio.file.{Files, Path, Paths}
 import java.util.Properties
 import java.util.concurrent.ConcurrentHashMap
-import scala.collection.immutable.Map
+import scala.collection.immutable.TreeMap
 
 object AnnexScalaInstance {
   // See the comment on getAnnexScalaInstance as to why this is necessary
@@ -48,7 +48,7 @@ object AnnexScalaInstance {
    * from a prior compilation in combination with a new ScalaInstance for the current compilation. Or there's some issue
    * with Scala's classpath caching.
    *
-   * If all three caches are enabled (this cache + Zinc claspath + Scala compiler), then the non-determinism seems go
+   * If all three caches are enabled (this cache + Zinc claspath + Scala compiler), then the non-determinism seems to go
    * away.
    *
    * If this cache is not used, but the Zinc classpath + Scala compiler caches are used, then non-determinsm shows up in
@@ -67,11 +67,20 @@ object AnnexScalaInstance {
    * any different from leaving Zinc's cache enabled.
    */
   private def getAnnexScalaInstance(allJars: Array[File], workDir: Path): AnnexScalaInstance = {
-    // We need to remove the sandbox prefix from the paths in order to compare them.
-    val mapBuilder = Map.newBuilder[Path, Path]
+    // We want to compare short paths to avoid the Bazel sandbox prefix and arch/config specific parts of the path
+    // We use a tree map because we want the keys sorted for comparison purposes
+    val mapBuilder = TreeMap.newBuilder[Path, Path]
+    val absoluteWorkDir = workDir.toAbsolutePath().normalize()
     allJars.foreach { jar =>
-      val comparableJarPath = jar.toPath().toAbsolutePath().normalize()
-      mapBuilder.addOne(jar.toPath -> workDir.toAbsolutePath().normalize().relativize(comparableJarPath))
+      val absoluteJarPath = jar.toPath().toAbsolutePath().normalize()
+      // Remove the sandbox prefix as well as the arch/config specific parts of the path.
+      mapBuilder.addOne(
+        jar.toPath ->
+          FileUtil.bazelShortPath(
+            absoluteWorkDir.relativize(absoluteJarPath),
+            replaceExternal = false,
+          ),
+      )
     }
     val workRequestJarToWorkerJar = mapBuilder.result()
 
@@ -84,7 +93,7 @@ object AnnexScalaInstance {
     // but that would require hashing the all the classpath jars on every compilation request. I
     // imagine that would cause a performance hit.
     //
-    // I also imagine it is extremeley rare to be mutating the contents of compiler classpath jars
+    // I also imagine it is extremely rare to be mutating the contents of compiler classpath jars
     // while keeping the names the same, e.g., generating new scala library jar for scala 2.13.14.
     // As a result I'm leaving this string based for now.
     val key = workRequestJarToWorkerJar.values.mkString(":")
diff --git a/src/main/scala/higherkindness/rules_scala/workers/common/FileUtil.scala b/src/main/scala/higherkindness/rules_scala/workers/common/FileUtil.scala
index 2e6f762a..0f2ba349 100644
--- a/src/main/scala/higherkindness/rules_scala/workers/common/FileUtil.scala
+++ b/src/main/scala/higherkindness/rules_scala/workers/common/FileUtil.scala
@@ -4,7 +4,7 @@ package workers.common
 import scala.annotation.tailrec
 import java.io.{File, IOException}
 import java.nio.channels.FileChannel
-import java.nio.file.{FileAlreadyExistsException, FileVisitResult, Files, Path, SimpleFileVisitor, StandardCopyOption, StandardOpenOption}
+import java.nio.file.{FileAlreadyExistsException, FileVisitResult, Files, Path, Paths, SimpleFileVisitor, StandardCopyOption, StandardOpenOption}
 import java.nio.file.attribute.BasicFileAttributes
 import java.util.zip.{ZipEntry, ZipInputStream, ZipOutputStream}
 
@@ -59,6 +59,29 @@ object FileUtil {
     path.getFileName().toString().stripPrefix("header_").stripPrefix("processed_")
   }
 
+  /**
+   * Given a Bazel path to the bazel output directory, return a path excluding the bazel configuration specific parts of
+   * the path. This is analogous to Bazel's File.short_path function. Fair warning: this function is super good enough,
+   * but is likely not perfect.
+   */
+  def bazelShortPath(path: Path, replaceExternal: Boolean = true): Path = {
+    val nameCount = path.getNameCount()
+    val pathString = path.toAbsolutePath().normalize().toString()
+
+    val shortPath = if (path.startsWith("bazel-out") && nameCount >= 4) {
+      path.subpath(3, nameCount)
+    } else {
+      path
+    }
+
+    // Handle difference between Bazel's external directory being referred to as .. in the short_path
+    if (replaceExternal && shortPath.startsWith("external")) {
+      Paths.get(shortPath.toString().replaceFirst("external", ".."))
+    } else {
+      shortPath
+    }
+  }
+
   def copy(source: Path, target: Path) = Files.walkFileTree(source, new CopyFileVisitor(source, target))
 
   def delete(path: Path) = Files.walkFileTree(path, new DeleteFileVisitor)