diff --git a/compiler_gym/bin/validate.py b/compiler_gym/bin/validate.py
index 94612324c..4e9fe83ed 100644
--- a/compiler_gym/bin/validate.py
+++ b/compiler_gym/bin/validate.py
@@ -207,7 +207,7 @@ def progress_message(i):
     progress_message(len(states))
     result_dicts = []
 
-    def dump_result_dicst_to_json():
+    def dump_result_dicts_to_json():
         with open(FLAGS.validation_logfile, "w") as f:
             json.dump(result_dicts, f)
 
@@ -223,9 +223,9 @@ def dump_result_dicst_to_json():
             walltimes.append(result.state.walltime)
 
         if not i % 10:
-            dump_result_dicst_to_json()
+            dump_result_dicts_to_json()
 
-    dump_result_dicst_to_json()
+    dump_result_dicts_to_json()
 
     # Print a summary footer.
     intermediate_print("\r\033[K----", "-" * name_col_width, "-----------", sep="")
diff --git a/compiler_gym/envs/llvm/datasets/cbench.py b/compiler_gym/envs/llvm/datasets/cbench.py
index fd001255c..fb48e5c67 100644
--- a/compiler_gym/envs/llvm/datasets/cbench.py
+++ b/compiler_gym/envs/llvm/datasets/cbench.py
@@ -15,11 +15,12 @@
 from collections import defaultdict
 from pathlib import Path
 from threading import Lock
-from typing import Callable, Dict, List, NamedTuple, Optional
+from typing import Callable, Dict, Iterable, List, NamedTuple, Optional
 
 import fasteners
 
 from compiler_gym.datasets import Benchmark, TarDatasetWithManifest
+from compiler_gym.datasets.benchmark import ValidationCallback
 from compiler_gym.datasets.uri import BenchmarkUri
 from compiler_gym.envs.llvm import llvm_benchmark
 from compiler_gym.service.proto import BenchmarkDynamicConfig, Command
@@ -269,7 +270,7 @@ def _make_cBench_validator(
     pre_execution_callback: Optional[Callable[[Path], None]] = None,
     sanitizer: Optional[LlvmSanitizer] = None,
     flakiness: int = 5,
-) -> Callable[["LlvmEnv"], Optional[ValidationError]]:  # noqa: F821
+) -> ValidationCallback:
     """Construct a validation callback for a cBench benchmark. See validator() for usage."""
     input_files = input_files or []
     output_files = output_files or []
@@ -407,6 +408,11 @@ def flaky_wrapped_cb(env: "LlvmEnv") -> Optional[ValidationError]:  # noqa: F821
                 # Timeout errors can be raised by the environment in case of a
                 # slow step / observation, and should be retried.
                 pass
+
+            # No point in repeating compilation failures as they are not flaky.
+            if error.type == "Compilation failed":
+                return error
+
             logger.warning(
                 "Validation callback failed (%s), attempt=%d/%d",
                 error.type,
@@ -415,7 +421,16 @@ def flaky_wrapped_cb(env: "LlvmEnv") -> Optional[ValidationError]:  # noqa: F821
             )
         return error
 
-    return flaky_wrapped_cb
+    # The flaky_wrapped_cb() function takes an environment and produces a single
+    # error. We need the validator to produce an iterable of errors.
+    def adapt_validator_return_type(
+        env: "LlvmEnv",  # noqa: F821
+    ) -> Iterable[ValidationError]:
+        error = flaky_wrapped_cb(env)
+        if error:
+            yield error
+
+    return adapt_validator_return_type
 
 
 def validator(
@@ -658,9 +673,7 @@ def __init__(self, site_data_base: Path):
 
 
 # A map from benchmark name to validation callbacks.
-VALIDATORS: Dict[
-    str, List[Callable[["LlvmEnv"], Optional[str]]]  # noqa: F821
-] = defaultdict(list)
+VALIDATORS: Dict[str, List[ValidationCallback]] = defaultdict(list)
 
 
 # A map from cBench benchmark path to a list of BenchmarkDynamicConfig messages,
diff --git a/tests/llvm/datasets/cbench_validate_test.py b/tests/llvm/datasets/cbench_validate_test.py
index 156e47b46..377f720d3 100644
--- a/tests/llvm/datasets/cbench_validate_test.py
+++ b/tests/llvm/datasets/cbench_validate_test.py
@@ -3,6 +3,8 @@
 # This source code is licensed under the MIT license found in the
 # LICENSE file in the root directory of this source tree.
 """Test for cBench semantics validation."""
+import pytest
+
 from compiler_gym import ValidationResult
 from compiler_gym.envs.llvm import LlvmEnv
 from tests.test_main import main
@@ -10,6 +12,7 @@
 pytest_plugins = ["tests.pytest_plugins.llvm"]
 
 
+@pytest.mark.timeout(600)
 def test_validate_benchmark_semantics(env: LlvmEnv, validatable_cbench_uri: str):
     """Run the validation routine on all benchmarks."""
     env.reward_space = "IrInstructionCount"
@@ -29,6 +32,7 @@ def test_validate_benchmark_semantics(env: LlvmEnv, validatable_cbench_uri: str)
     assert result.okay()
 
 
+@pytest.mark.timeout(600)
 def test_non_validatable_benchmark_validate(
     env: LlvmEnv, non_validatable_cbench_uri: str
 ):