diff --git a/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/BUILD b/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/BUILD
index 015b609ec2290a..bb92bbbe232063 100644
--- a/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/BUILD
+++ b/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/BUILD
@@ -60,6 +60,7 @@ java_library(
         "//src/main/java/net/starlark/java/syntax",
         "//third_party:auto_value",
         "//third_party:error_prone_annotations",
+        "//third_party:flogger",
         "//third_party:guava",
         "//third_party:java-diff-utils",
         "//third_party:jsr305",
diff --git a/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/StarlarkBaseExternalContext.java b/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/StarlarkBaseExternalContext.java
index 688ac7f97160ef..0248461ed72bbf 100644
--- a/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/StarlarkBaseExternalContext.java
+++ b/src/main/java/com/google/devtools/build/lib/bazel/repository/starlark/StarlarkBaseExternalContext.java
@@ -24,6 +24,7 @@
 import com.google.common.collect.ImmutableMap;
 import com.google.common.collect.ImmutableSortedMap;
 import com.google.common.collect.Maps;
+import com.google.common.flogger.GoogleLogger;
 import com.google.common.util.concurrent.Futures;
 import com.google.devtools.build.lib.actions.FileValue;
 import com.google.devtools.build.lib.analysis.BlazeDirectories;
@@ -79,6 +80,7 @@
 import java.nio.file.InvalidPathException;
 import java.nio.file.Paths;
 import java.time.Duration;
+import java.time.Instant;
 import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.Base64;
@@ -148,6 +150,8 @@ private interface AsyncTask extends SilentCloseable {
     void close();
   }
 
+  private static final GoogleLogger logger = GoogleLogger.forEnclosingClass();
+
   /** Max. length of command line args added as a profiler description. */
   private static final int MAX_PROFILE_ARGS_LEN = 512;
 
@@ -1110,21 +1114,55 @@ public StructImpl downloadAndExtract(
     }
 
     StructImpl downloadResult = calculateDownloadResult(checksum, downloadedPath);
-    try {
-      if (downloadDirectory.exists()) {
-        downloadDirectory.deleteTree();
+    deleteTreeWithRetries(downloadDirectory);
+    return downloadResult;
+  }
+
+  /**
+   * This method wraps the deleteTree method in a retry loop, to solve an issue when trying to
+   * recursively clean up temporary directories during dependency downloads when they are stored on
+   * filesystems where unlinking a file may not be immediately reflected in a list of its parent
+   * directory. Specifically, the symptom of this problem was the entire bazel build aborting
+   * because during the cleanup of a dependency download (e.g Rust crate), there was an IOException
+   * because the parent directory being removed was "not empty" (yet). Please see
+   * https://github.com/bazelbuild/bazel/issues/23687 and
+   * https://github.com/bazelbuild/bazel/issues/20013 for further details.
+   *
+   * @param downloadDirectory
+   * @throws RepositoryFunctionException
+   */
+  private static void deleteTreeWithRetries(Path downloadDirectory)
+      throws RepositoryFunctionException {
+    Instant start = Instant.now();
+    Instant deadline = start.plus(Duration.ofSeconds(5));
+
+    for (int attempts = 1; ; attempts++) {
+      try {
+        if (downloadDirectory.exists()) {
+          downloadDirectory.deleteTree();
+        }
+        if (attempts > 1) {
+          long elapsedMillis = Duration.between(start, Instant.now()).toMillis();
+          logger.atInfo().log(
+              "Deleting %s took %d attempts over %dms.",
+              downloadDirectory.getPathString(), attempts, elapsedMillis);
+        }
+        break;
+      } catch (IOException e) {
+        if (Instant.now().isAfter(deadline)) {
+          throw new RepositoryFunctionException(
+              new IOException(
+                  "Couldn't delete temporary directory ("
+                      + downloadDirectory.getPathString()
+                      + ") after "
+                      + attempts
+                      + " attempts: "
+                      + e.getMessage(),
+                  e),
+              Transience.TRANSIENT);
+        }
       }
-    } catch (IOException e) {
-      throw new RepositoryFunctionException(
-          new IOException(
-              "Couldn't delete temporary directory ("
-                  + downloadDirectory.getPathString()
-                  + "): "
-                  + e.getMessage(),
-              e),
-          Transience.TRANSIENT);
     }
-    return downloadResult;
   }
 
   @StarlarkMethod(