diff --git a/src/pipgrip/cli.py b/src/pipgrip/cli.py
index b70f192..636db95 100755
--- a/src/pipgrip/cli.py
+++ b/src/pipgrip/cli.py
@@ -52,7 +52,12 @@
 from pipgrip.libs.mixology.package import Package
 from pipgrip.libs.mixology.version_solver import VersionSolver
 from pipgrip.package_source import PackageSource, render_pin
-from pipgrip.pipper import install_packages, read_requirements
+from pipgrip.pipper import (
+    BUILD_FAILURE_STR,
+    REPORT_FAILURE_STR,
+    install_packages,
+    read_requirements,
+)
 
 logging.basicConfig(format="%(levelname)s: %(message)s")
 logger = logging.getLogger()
@@ -479,7 +484,7 @@ def main(
             exc = None
         except RuntimeError as e:
             # RuntimeError coming from pipgrip.pipper
-            if "Failed to download/build wheel" not in str(e):
+            if REPORT_FAILURE_STR not in str(e) and BUILD_FAILURE_STR not in str(e):
                 # only continue handling expected RuntimeErrors
                 raise
             solution = solver.solution
diff --git a/src/pipgrip/pipper.py b/src/pipgrip/pipper.py
index c2e291d..b503066 100644
--- a/src/pipgrip/pipper.py
+++ b/src/pipgrip/pipper.py
@@ -49,6 +49,10 @@
 
 logger = logging.getLogger(__name__)
 
+REPORT_FAILURE_STR = "Failed to get report for"
+BUILD_FAILURE_STR = "Failed to download/build wheel for"
+VERSIONS_FAILURE_STR = "Failed to get available versions for"
+
 
 def read_requirements(path):
     re_comments = re.compile(r"(?:^|\s+)#")
@@ -292,7 +296,7 @@ def _get_available_versions(package, index_url, extra_index_url, pre):
             ]
             _available_versions_cache[cache_key] = available_versions
             return available_versions
-    raise RuntimeError("Failed to get available versions for {}".format(package))
+    raise RuntimeError("{} {}".format(VERSIONS_FAILURE_STR, package))
 
 
 def _get_package_report(
@@ -357,7 +361,7 @@ def _get_package_report(
                 package, output.strip()
             )
         )
-        raise RuntimeError("Failed to get report for {}".format(package))
+        raise RuntimeError("{} {}".format(REPORT_FAILURE_STR, package))
     else:
         with io.open(report_file, "r", encoding="utf-8") as fp:
             return json.load(fp)
@@ -397,7 +401,7 @@ def _download_wheel(
                 package, output.strip()
             )
         )
-        raise RuntimeError("Failed to download/build wheel for {}".format(package))
+        raise RuntimeError("{} {}".format(BUILD_FAILURE_STR, package))
     out = out.splitlines()[::-1]
     abs_wheel_dir_lower = abs_wheel_dir.lower()
     cwd_wheel_dir_lower = cwd_wheel_dir.lower()
@@ -474,7 +478,7 @@ def _download_wheel(
             "\n".join(out[::-1])
         )
     )
-    raise RuntimeError("Failed to download/build wheel for {}".format(package))
+    raise RuntimeError("{} {}".format(BUILD_FAILURE_STR, package))
 
 
 def _extract_metadata(wheel_fname):
diff --git a/tests/test_cli.py b/tests/test_cli.py
index cb8fa37..294287a 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -30,6 +30,9 @@
 # OF THIS SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
 #
 # SPDX-License-Identifier: BSD-3-Clause
+import logging
+import subprocess
+
 import pytest
 from click.testing import CliRunner
 
@@ -141,7 +144,13 @@ def mock_stream_bash_command(*args, **kwargs):
     return "I passed"
 
 
-def invoke_patched(func, arguments, monkeypatch, use_report=False, **kwargs):
+def mock_stream_bash_command_failure(*args, **kwargs):
+    raise subprocess.CalledProcessError(1, args[0])
+
+
+def invoke_patched(
+    func, arguments, monkeypatch, use_report=False, mock_failure=False, **kwargs
+):
     def default_environment():
         return {
             "implementation_name": "cpython",
@@ -157,16 +166,28 @@ def default_environment():
             "sys_platform": "linux",
         }
 
-    monkeypatch.setattr(
-        pipgrip.pipper,
-        "_download_wheel",
-        mock_download_wheel,
-    )
-    monkeypatch.setattr(
-        pipgrip.pipper,
-        "_get_package_report",
-        mock_get_package_report,
-    )
+    if mock_failure:
+        monkeypatch.setattr(
+            pipgrip.pipper,
+            "stream_bash_command",
+            mock_stream_bash_command_failure,
+        )
+    else:
+        monkeypatch.setattr(
+            pipgrip.pipper,
+            "stream_bash_command",
+            mock_stream_bash_command,
+        )
+        monkeypatch.setattr(
+            pipgrip.pipper,
+            "_download_wheel",
+            mock_download_wheel,
+        )
+        monkeypatch.setattr(
+            pipgrip.pipper,
+            "_get_package_report",
+            mock_get_package_report,
+        )
     if use_report:
         monkeypatch.setattr(
             pipgrip.pipper,
@@ -189,11 +210,6 @@ def default_environment():
         "default_environment",
         default_environment,
     )
-    monkeypatch.setattr(
-        pipgrip.pipper,
-        "stream_bash_command",
-        mock_stream_bash_command,
-    )
     runner = CliRunner()
     return runner.invoke(main, arguments, **kwargs)
 
@@ -426,6 +442,24 @@ def test_solutions(arguments, expected, monkeypatch):
     ), "Unexpected output:\n{}".format(result.output.strip())
 
 
+def test_failue_build(monkeypatch, caplog):
+    caplog.set_level(logging.DEBUG)
+    arguments = ["requests[socks]"]
+    result = invoke_patched(main, arguments, monkeypatch, mock_failure=True)
+    assert result.exit_code
+    assert "Best guess" in caplog.text
+
+
+def test_failue_report(monkeypatch, caplog):
+    caplog.set_level(logging.DEBUG)
+    arguments = ["requests[socks]"]
+    result = invoke_patched(
+        main, arguments, monkeypatch, use_report=True, mock_failure=True
+    )
+    assert result.exit_code
+    assert "Best guess" in caplog.text
+
+
 @pytest.mark.parametrize(
     "arguments",
     [