diff --git a/pex/build_system/pep_517.py b/pex/build_system/pep_517.py
index b085f47b2..f7d87ef93 100644
--- a/pex/build_system/pep_517.py
+++ b/pex/build_system/pep_517.py
@@ -186,7 +186,13 @@ def _invoke_build_hook(
             stderr=subprocess.PIPE,
         )
         return SpawnedJob.file(
-            Job(command=args, process=process),
+            Job(
+                command=args,
+                process=process,
+                context="PEP-517:{hook_method} at {project_directory}".format(
+                    hook_method=hook_method, project_directory=project_directory
+                ),
+            ),
             output_file=fp.name,
             result_func=lambda file_content: json.loads(file_content.decode("utf-8")),
         )
diff --git a/pex/dist_metadata.py b/pex/dist_metadata.py
index 84621edbc..daee47054 100644
--- a/pex/dist_metadata.py
+++ b/pex/dist_metadata.py
@@ -651,22 +651,40 @@ def requires_dists(location):
         )
 
 
+# Frozen exception types don't work under 3.11+ where the `__traceback__` attribute can be set
+# after construction in some cases.
+@attr.s
 class RequirementParseError(Exception):
     """Indicates and invalid requirement string.
 
     See PEP-508: https://www.python.org/dev/peps/pep-0508
     """
 
+    error = attr.ib()  # type: Any
+    source = attr.ib(default=None)  # type: Optional[str]
+
+    def __str__(self):
+        # type: () -> str
+        if not self.source:
+            return str(self.error)
+        return "Failed to parse a requirement of {source}: {err}".format(
+            err=self.error, source=self.source
+        )
+
 
 @attr.s(frozen=True)
 class Constraint(object):
     @classmethod
-    def parse(cls, constraint):
-        # type: (Text) -> Constraint
+    def parse(
+        cls,
+        constraint,  # type: Text
+        source=None,  # type: Optional[str]
+    ):
+        # type: (...) -> Constraint
         try:
             return cls.from_packaging_requirement(PackagingRequirement(constraint))
         except InvalidRequirement as e:
-            raise RequirementParseError(str(e))
+            raise RequirementParseError(str(e), source=source)
 
     @classmethod
     def from_packaging_requirement(cls, requirement):
@@ -777,12 +795,16 @@ def as_requirement(self):
 @attr.s(frozen=True)
 class Requirement(Constraint):
     @classmethod
-    def parse(cls, requirement):
-        # type: (Text) -> Requirement
+    def parse(
+        cls,
+        requirement,  # type: Text
+        source=None,  # type: Optional[str]
+    ):
+        # type: (...) -> Requirement
         try:
             return cls.from_packaging_requirement(PackagingRequirement(requirement))
         except InvalidRequirement as e:
-            raise RequirementParseError(str(e))
+            raise RequirementParseError(str(e), source=source)
 
     @classmethod
     def from_packaging_requirement(cls, requirement):
diff --git a/pex/interpreter.py b/pex/interpreter.py
index 395358d38..bb483e8b0 100644
--- a/pex/interpreter.py
+++ b/pex/interpreter.py
@@ -46,7 +46,6 @@
         Mapping,
         MutableMapping,
         Optional,
-        Sequence,
         Text,
         Tuple,
         Union,
@@ -1566,45 +1565,6 @@ def __repr__(self):
         )
 
 
-def spawn_python_job(
-    args,  # type: Iterable[str]
-    env=None,  # type: Optional[Mapping[str, str]]
-    interpreter=None,  # type: Optional[PythonInterpreter]
-    expose=None,  # type: Optional[Sequence[str]]
-    pythonpath=None,  # type: Optional[Iterable[str]]
-    **subprocess_kwargs  # type: Any
-):
-    # type: (...) -> Job
-    """Spawns a python job.
-
-    :param args: The arguments to pass to the python interpreter.
-    :param env: The environment to spawn the python interpreter process in. Defaults to the ambient
-                environment.
-    :param interpreter: The interpreter to use to spawn the python job. Defaults to the current
-                        interpreter.
-    :param expose: The names of any vendored distributions to expose to the spawned python process.
-                   These will be appended to `pythonpath` if passed.
-    :param pythonpath: The PYTHONPATH to expose to the spawned python process. These will be
-                       pre-pended to the `expose` path if passed.
-    :param subprocess_kwargs: Any additional :class:`subprocess.Popen` kwargs to pass through.
-    :returns: A job handle to the spawned python process.
-    """
-    pythonpath = list(pythonpath or ())
-    subprocess_env = dict(env or os.environ)
-    if expose:
-        # In order to expose vendored distributions with their un-vendored import paths in-tact, we
-        # need to set `__PEX_UNVENDORED__`. See: vendor.__main__.ImportRewriter._modify_import.
-        subprocess_env["__PEX_UNVENDORED__"] = ",".join(expose)
-
-        pythonpath.extend(third_party.expose(expose, interpreter=interpreter))
-
-    interpreter = interpreter or PythonInterpreter.get()
-    cmd, process = interpreter.open_process(
-        args=args, pythonpath=pythonpath, env=subprocess_env, **subprocess_kwargs
-    )
-    return Job(command=cmd, process=process)
-
-
 # See the "Test results from various systems" table here:
 #  https://www.in-ulm.de/~mascheck/various/shebang/#length
 MAX_SHEBANG_LENGTH = 512 if sys.platform == "darwin" else 128
diff --git a/pex/jobs.py b/pex/jobs.py
index ab3bbc320..bae04ccc6 100644
--- a/pex/jobs.py
+++ b/pex/jobs.py
@@ -63,19 +63,33 @@ def __init__(
             exitcode,  # type: int
             stderr,  # type: Optional[Text]
             message,  # type: str
+            context=None,  # type: Optional[str]
         ):
             # type: (...) -> None
-            super(Job.Error, self).__init__(message)
+            super(Job.Error, self).__init__(
+                "{ctx}: {msg}".format(ctx=context, msg=message) if context else message
+            )
             self.pid = pid
             self.command = command
             self.exitcode = exitcode
             self.stderr = stderr
+            self._context = context
+
+        def contextualized_stderr(self):
+            # type: () -> Iterator[Text]
+            if self.stderr:
+                for line in self.stderr.splitlines():
+                    if not self._context:
+                        yield line
+                    else:
+                        yield "{ctx}: {line}".format(ctx=self._context, line=line)
 
     def __init__(
         self,
         command,  # type: Iterable[str]
         process,  # type: subprocess.Popen
         finalizer=None,  # type: Optional[Callable[[int], None]]
+        context=None,  # type: Optional[str]
     ):
         # type: (...) -> None
         """
@@ -84,10 +98,13 @@ def __init__(
         :param finalizer: An optional cleanup function to call exactly once with the process return
                           code when the underlying process terminates in the course of calling this
                           job's public methods.
+        :param context: An optional context labeling the job that will be used to decorate error
+                        information.
         """
         self._command = tuple(command)
         self._process = process
         self._finalizer = finalizer
+        self._context = context
 
     def wait(self):
         # type: () -> None
@@ -153,6 +170,7 @@ def create_error(
             exitcode=self._process.returncode,
             stderr=err,
             message=msg,
+            context=self._context,
         )
 
     def _finalize_job(self):
@@ -407,7 +425,7 @@ def job_error_message(
             pid=job_error.pid,
             command=" ".join(job_error.command),
             exitcode=job_error.exitcode,
-            stderr=job_error.stderr,
+            stderr="\n".join(job_error.contextualized_stderr()),
         )
 
     @abstractmethod
diff --git a/pex/pip/dependencies/requires.py b/pex/pip/dependencies/requires.py
index 8938ac564..ef3c0d293 100644
--- a/pex/pip/dependencies/requires.py
+++ b/pex/pip/dependencies/requires.py
@@ -22,7 +22,7 @@ def requires(self, *args, **kwargs):
             modified_requires = []
             orig = orig_requires(self, *args, **kwargs)
             for req in orig:
-                requirement = PexRequirement.parse(str(req))
+                requirement = PexRequirement.parse(str(req), source=repr(self))
                 excluded_by = dependency_configuration.excluded_by(requirement)
                 if excluded_by:
                     logger.debug(
diff --git a/pex/pip/log_analyzer.py b/pex/pip/log_analyzer.py
index a30d2654b..a2701c2cb 100644
--- a/pex/pip/log_analyzer.py
+++ b/pex/pip/log_analyzer.py
@@ -7,6 +7,7 @@
 import subprocess
 from abc import abstractmethod
 
+from pex.common import safe_delete
 from pex.jobs import Job
 from pex.typing import TYPE_CHECKING, Generic
 
@@ -81,7 +82,7 @@ def __init__(
         self._log = log
         self._log_analyzers = list(log_analyzers)
         self._preserve_log = preserve_log
-        super(LogScrapeJob, self).__init__(command, process, finalizer=finalizer)
+        super(LogScrapeJob, self).__init__(command, process, finalizer=finalizer, context="pip")
 
     def _check_returncode(self, stderr=None):
         # type: (Optional[bytes]) -> None
@@ -90,6 +91,7 @@ def _check_returncode(self, stderr=None):
             for analyzer in self._log_analyzers
             if analyzer.should_collect(self._process.returncode)
         ]
+        analyzed_stderr = b""  # type: bytes
         if activated_analyzers:
             collected = []
             # A process may fail so early that there is no log file to analyze.
@@ -100,7 +102,7 @@ def _check_returncode(self, stderr=None):
                     for line in fp:
                         if not activated_analyzers:
                             break
-                        for index, analyzer in enumerate(activated_analyzers):
+                        for index, analyzer in tuple(enumerate(activated_analyzers)):
                             result = analyzer.analyze(line)
                             if isinstance(result.data, ErrorMessage):
                                 collected.append(result.data)
@@ -110,7 +112,21 @@ def _check_returncode(self, stderr=None):
                                     break
                 for analyzer in activated_analyzers:
                     analyzer.analysis_completed()
-                if not self._preserve_log:
-                    os.unlink(self._log)
-                stderr = (stderr or b"") + "".join(collected).encode("utf-8")
-        super(LogScrapeJob, self)._check_returncode(stderr=stderr)
+            if collected:
+                analyzed_stderr = "".join(collected).encode("utf-8")
+
+        # Fall back to displaying the Pip logs in full if we have no stderr output or analysis. It's
+        # likely overwhelming, but better than silence and useful for debugging.
+        if (
+            not stderr
+            and not analyzed_stderr
+            and self._process.returncode != 0
+            and os.path.isfile(self._log)
+        ):
+            with open(self._log, "rb") as fp:
+                analyzed_stderr = fp.read()
+
+        if not self._preserve_log:
+            safe_delete(self._log)
+
+        super(LogScrapeJob, self)._check_returncode(stderr=(stderr or b"") + analyzed_stderr)
diff --git a/pex/pip/tool.py b/pex/pip/tool.py
index 1bb7273e3..a407a94b9 100644
--- a/pex/pip/tool.py
+++ b/pex/pip/tool.py
@@ -50,6 +50,7 @@
         Iterator,
         List,
         Mapping,
+        Match,
         Optional,
         Sequence,
         Tuple,
@@ -233,6 +234,42 @@ def analyze(self, line):
         return self.Continue()
 
 
+@attr.s
+class _PexIssue2113Analyzer(ErrorAnalyzer):
+    # Improves obscure error output described in: https://github.com/pex-tool/pex/issues/2113
+
+    _strip = attr.ib(default=0, init=False)  # type: Optional[int]
+    _command = attr.ib(default=None, init=False)  # type: Optional[str]
+    _command_output = attr.ib(factory=list, init=False)  # type: List[str]
+    _command_errored = attr.ib(default=None, init=False)  # type: Optional[Match]
+
+    def analyze(self, line):
+        # type: (str) -> ErrorAnalysis
+
+        if self._command_errored:
+            return self.Complete()
+
+        match = re.match(r"^(?P<timestamp>\S+)\s+Running command (?P<command>.*)$", line)
+        if match:
+            self._strip = len(match.group("timestamp"))
+            self._command = match.group("command")
+            del self._command_output[:]
+            self._command_output.append(line[self._strip :])
+            return self.Continue()
+
+        if self._command:
+            self._command_errored = re.match(
+                r"^\S+\s+ERROR:.*{command}".format(command=re.escape(self._command)), line
+            )
+            if self._command_errored:
+                return self.Continue(
+                    ErrorMessage("".join(self._command_output + [line[self._strip :]]))
+                )
+            self._command_output.append(line[self._strip :])
+
+        return self.Continue()
+
+
 @attr.s(frozen=True)
 class PipVenv(object):
     venv_dir = attr.ib()  # type: str
@@ -414,7 +451,7 @@ def _spawn_pip_isolated_job(
             extra_env=extra_env,
             **popen_kwargs
         )
-        return Job(command=command, process=process, finalizer=finalizer)
+        return Job(command=command, process=process, finalizer=finalizer, context="pip")
 
     @staticmethod
     def _iter_build_configuration_options(build_configuration):
@@ -540,57 +577,53 @@ def spawn_download_distributions(
         ):
             log_analyzers.append(_Issue9420Analyzer())
 
-        log = None
+        # Most versions of Pip hide useful information when a metadata build command fails; this
+        # analyzer brings that build failure information to the fore.
+        log_analyzers.append(_PexIssue2113Analyzer())
+
         popen_kwargs = {}
         finalizer = None
-        if log_analyzers:
-            prefix = "pex-pip-log."
-            log = os.path.join(
-                mkdtemp(prefix=prefix) if preserve_log else safe_mkdtemp(prefix=prefix), "pip.log"
-            )
-            if preserve_log:
-                TRACER.log(
-                    "Preserving `pip download` log at {log_path}".format(log_path=log),
-                    V=ENV.PEX_VERBOSE,
-                )
-
-            download_cmd = ["--log", log] + download_cmd
-            # N.B.: The `pip -q download ...` command is quiet but
-            # `pip -q --log log.txt download ...` leaks download progress bars to stdout. We work
-            # around this by sending stdout to the bit bucket.
-            popen_kwargs["stdout"] = open(os.devnull, "wb")
-
-            if ENV.PEX_VERBOSE > 0:
-                tailer = Tailer.tail(
-                    path=log,
-                    output=get_stderr_bytes_buffer(),
-                    filters=(
-                        re.compile(
-                            r"^.*(pip is looking at multiple versions of [^\s+] to determine "
-                            r"which version is compatible with other requirements\. This could "
-                            r"take a while\.).*$"
-                        ),
-                        re.compile(
-                            r"^.*(This is taking longer than usual. You might need to provide "
-                            r"the dependency resolver with stricter constraints to reduce "
-                            r"runtime\. If you want to abort this run, you can press "
-                            r"Ctrl \+ C to do so\. To improve how pip performs, tell us what "
-                            r"happened here: https://pip\.pypa\.io/surveys/backtracking).*$"
-                        ),
-                    ),
-                )
-
-                def finalizer(_):
-                    # type: (int) -> None
-                    tailer.stop()
 
-        elif preserve_log:
+        prefix = "pex-pip-log."
+        log = os.path.join(
+            mkdtemp(prefix=prefix) if preserve_log else safe_mkdtemp(prefix=prefix), "pip.log"
+        )
+        if preserve_log:
             TRACER.log(
-                "The `pip download` log is not being utilized, to see more `pip download` "
-                "details, re-run with more Pex verbosity (more `-v`s).",
+                "Preserving `pip download` log at {log_path}".format(log_path=log),
                 V=ENV.PEX_VERBOSE,
             )
 
+        download_cmd = ["--log", log] + download_cmd
+        # N.B.: The `pip -q download ...` command is quiet but
+        # `pip -q --log log.txt download ...` leaks download progress bars to stdout. We work
+        # around this by sending stdout to the bit bucket.
+        popen_kwargs["stdout"] = open(os.devnull, "wb")
+
+        if ENV.PEX_VERBOSE > 0:
+            tailer = Tailer.tail(
+                path=log,
+                output=get_stderr_bytes_buffer(),
+                filters=(
+                    re.compile(
+                        r"^.*(pip is looking at multiple versions of [^\s+] to determine "
+                        r"which version is compatible with other requirements\. This could "
+                        r"take a while\.).*$"
+                    ),
+                    re.compile(
+                        r"^.*(This is taking longer than usual. You might need to provide "
+                        r"the dependency resolver with stricter constraints to reduce "
+                        r"runtime\. If you want to abort this run, you can press "
+                        r"Ctrl \+ C to do so\. To improve how pip performs, tell us what "
+                        r"happened here: https://pip\.pypa\.io/surveys/backtracking).*$"
+                    ),
+                ),
+            )
+
+            def finalizer(_):
+                # type: (int) -> None
+                tailer.stop()
+
         command, process = self._spawn_pip_isolated(
             download_cmd,
             package_index_configuration=package_index_configuration,
@@ -599,12 +632,9 @@ def finalizer(_):
             extra_env=extra_env,
             **popen_kwargs
         )
-        if log:
-            return LogScrapeJob(
-                command, process, log, log_analyzers, preserve_log=preserve_log, finalizer=finalizer
-            )
-        else:
-            return Job(command, process)
+        return LogScrapeJob(
+            command, process, log, log_analyzers, preserve_log=preserve_log, finalizer=finalizer
+        )
 
     def _ensure_wheel_installed(self, package_index_configuration=None):
         # type: (Optional[PackageIndexConfiguration]) -> None
diff --git a/pex/resolve/downloads.py b/pex/resolve/downloads.py
index edf8b2085..92e07b7ff 100644
--- a/pex/resolve/downloads.py
+++ b/pex/resolve/downloads.py
@@ -186,6 +186,11 @@ def download(
             try:
                 self._download(url=artifact.url, download_dir=dest_dir).wait()
             except Job.Error as e:
-                return Error((e.stderr or str(e)).splitlines()[-1])
+                error_lines = list(e.contextualized_stderr()) or str(e).splitlines()
+                return Error(
+                    os.linesep.join(error_lines)
+                    if "See above for details" in error_lines[-1]
+                    else error_lines[-1]
+                )
         hashing.file_hash(dest_file, digest)
         return artifact.filename
diff --git a/pex/resolve/lock_resolver.py b/pex/resolve/lock_resolver.py
index f84bce95b..91e2aa28c 100644
--- a/pex/resolve/lock_resolver.py
+++ b/pex/resolve/lock_resolver.py
@@ -400,7 +400,7 @@ def resolve_from_lock(
                             index=index,
                             pin=downloadable_artifact.pin,
                             url=downloadable_artifact.artifact.url.download_url,
-                            error=error,
+                            error="\n    ".join(str(error).splitlines()),
                         )
                         for index, (downloadable_artifact, error) in enumerate(
                             download_errors.items(), start=1
diff --git a/testing/__init__.py b/testing/__init__.py
index e020a9bb9..7ab8580da 100644
--- a/testing/__init__.py
+++ b/testing/__init__.py
@@ -29,7 +29,6 @@
 from pex.pex_info import PexInfo
 from pex.pip.installation import get_pip
 from pex.resolve.configured_resolver import ConfiguredResolver
-from pex.resolve.resolver_configuration import PipConfiguration
 from pex.typing import TYPE_CHECKING
 from pex.util import named_temporary_file
 from pex.venv.virtualenv import InstallationChoice, Virtualenv
@@ -211,7 +210,7 @@ def bdist(self):
         # type: () -> str
         get_pip(
             interpreter=self._interpreter,
-            resolver=ConfiguredResolver(pip_configuration=PipConfiguration()),
+            resolver=ConfiguredResolver.default(),
         ).spawn_build_wheels(
             distributions=[self._source_dir],
             wheel_dir=self._wheel_dir,
diff --git a/tests/integration/cli/commands/test_issue_1801.py b/tests/integration/cli/commands/test_issue_1801.py
index de548fe53..e4f63d365 100644
--- a/tests/integration/cli/commands/test_issue_1801.py
+++ b/tests/integration/cli/commands/test_issue_1801.py
@@ -4,12 +4,7 @@
 import os.path
 import re
 
-import pytest
-from colors import green
-
 from pex.resolve.lockfile import json_codec
-from pex.resolve.resolver_configuration import ResolverVersion
-from testing import run_pex_command
 from testing.cli import run_pex3
 
 
@@ -63,31 +58,3 @@ def test_preserve_pip_download_log():
     assert artifact.url.download_url.endswith(expected_url_suffix)
     assert expected_algorithm == artifact.fingerprint.algorithm
     assert expected_hash == artifact.fingerprint.hash
-
-
-@pytest.mark.skipif(
-    ResolverVersion.default() is ResolverVersion.PIP_2020,
-    reason=(
-        "The PIP_2020 resolver triggers download analysis in normal resolves but this test is "
-        "concerned with the case when there is no analysis to be performed."
-    ),
-)
-def test_preserve_pip_download_log_none():
-    # type: () -> None
-
-    result = run_pex_command(
-        args=[
-            "ansicolors==1.1.8",
-            "--preserve-pip-download-log",
-            "--",
-            "-c",
-            "import colors; print(colors.green('42'))",
-        ],
-        quiet=True,
-    )
-    result.assert_success()
-    assert green("42") == result.output.strip()
-    assert (
-        "pex: The `pip download` log is not being utilized, to see more `pip download` details, "
-        "re-run with more Pex verbosity (more `-v`s).\n"
-    ) in result.error, result.error
diff --git a/tests/integration/cli/commands/test_lock.py b/tests/integration/cli/commands/test_lock.py
index cb57fa3a7..78f95d97f 100644
--- a/tests/integration/cli/commands/test_lock.py
+++ b/tests/integration/cli/commands/test_lock.py
@@ -883,33 +883,31 @@ def test_update_targeted_impossible(
     pip_version = json_codec.load(lock_file_path).pip_version
     if pip_version == PipVersion.v20_3_4_patched:
         expected_lines = [
-            "ERROR: Could not find a version that satisfies the requirement urllib3<1.27,>=1.21.1 "
-            "(from requests)",
-            "ERROR: No matching distribution found for urllib3<1.27,>=1.21.1",
-            "",
+            "pip: ERROR: Could not find a version that satisfies the requirement "
+            "urllib3<1.27,>=1.21.1 (from requests)",
+            "pip: ERROR: No matching distribution found for urllib3<1.27,>=1.21.1",
         ]
     else:
         expected_lines = [
-            "ERROR: Cannot install requests==2.26.0 because these package versions have "
+            "pip: ERROR: Cannot install requests==2.26.0 because these package versions have "
             "conflicting dependencies.",
-            "ERROR: ResolutionImpossible: for help visit "
+            "pip: ERROR: ResolutionImpossible: for help visit "
             "https://pip.pypa.io/en/latest/topics/dependency-resolution/"
             "#dealing-with-dependency-conflicts",
-            " ",
-            " The conflict is caused by:",
-            "     requests 2.26.0 depends on urllib3<1.27 and >=1.21.1",
-            "     The user requested (constraint) urllib3<1.16",
-            " ",
-            " To fix this you could try to:",
-            " 1. loosen the range of package versions you've specified",
-            " 2. remove package versions to allow {pip_to} attempt to solve the dependency "
+            "pip:  ",
+            "pip:  The conflict is caused by:",
+            "pip:      requests 2.26.0 depends on urllib3<1.27 and >=1.21.1",
+            "pip:      The user requested (constraint) urllib3<1.16",
+            "pip:  ",
+            "pip:  To fix this you could try to:",
+            "pip:  1. loosen the range of package versions you've specified",
+            "pip:  2. remove package versions to allow {pip_to} attempt to solve the dependency "
             "conflict".format(
                 pip_to="pip" if pip_version.version < PipVersion.v24_1.version else "pip to"
             ),
-            "",
         ]
     assert expected_lines == error_lines[12:], os.linesep.join(
-        difflib.unified_diff(os.linesep.join(expected_lines), os.linesep.join(error_lines[12:]))
+        difflib.unified_diff(expected_lines, error_lines[12:])
     )
 
     # The pip legacy resolver, though is not strict and will let us get away with this.
@@ -984,34 +982,32 @@ def test_update_add_impossible(
     pip_version = json_codec.load(lock_file_path).pip_version
     if pip_version == PipVersion.v20_3_4_patched:
         expected_lines = [
-            "ERROR: Could not find a version that satisfies the requirement certifi<2017.4.17 "
+            "pip: ERROR: Could not find a version that satisfies the requirement certifi<2017.4.17 "
             "(from conflicting-certifi-requirement)",
-            "ERROR: No matching distribution found for certifi<2017.4.17",
-            "",
+            "pip: ERROR: No matching distribution found for certifi<2017.4.17",
         ]
     else:
         expected_lines = [
-            "ERROR: Cannot install conflicting-certifi-requirement==1.2.3 and requests==2.26.0 "
-            "because these package versions have conflicting dependencies.",
-            "ERROR: ResolutionImpossible: for help visit "
+            "pip: ERROR: Cannot install conflicting-certifi-requirement==1.2.3 and "
+            "requests==2.26.0 because these package versions have conflicting dependencies.",
+            "pip: ERROR: ResolutionImpossible: for help visit "
             "https://pip.pypa.io/en/latest/topics/dependency-resolution/"
             "#dealing-with-dependency-conflicts",
-            " ",
-            " The conflict is caused by:",
-            "     requests 2.26.0 depends on certifi>=2017.4.17",
-            "     conflicting-certifi-requirement 1.2.3 depends on certifi<2017.4.17",
-            "     The user requested (constraint) certifi==2021.5.30",
-            " ",
-            " To fix this you could try to:",
-            " 1. loosen the range of package versions you've specified",
-            " 2. remove package versions to allow {pip_to} attempt to solve the dependency "
+            "pip:  ",
+            "pip:  The conflict is caused by:",
+            "pip:      requests 2.26.0 depends on certifi>=2017.4.17",
+            "pip:      conflicting-certifi-requirement 1.2.3 depends on certifi<2017.4.17",
+            "pip:      The user requested (constraint) certifi==2021.5.30",
+            "pip:  ",
+            "pip:  To fix this you could try to:",
+            "pip:  1. loosen the range of package versions you've specified",
+            "pip:  2. remove package versions to allow {pip_to} attempt to solve the dependency "
             "conflict".format(
                 pip_to="pip" if pip_version.version < PipVersion.v24_1.version else "pip to"
             ),
-            "",
         ]
     assert expected_lines == error_lines[13:], os.linesep.join(
-        difflib.unified_diff(os.linesep.join(expected_lines), os.linesep.join(error_lines[12:]))
+        difflib.unified_diff(expected_lines, error_lines[12:])
     )
 
     # The pip legacy resolver, though is not strict and will let us get away with this.
diff --git a/tests/integration/cli/commands/test_lock_resolve_auth.py b/tests/integration/cli/commands/test_lock_resolve_auth.py
index 327aec8ad..71b848bda 100644
--- a/tests/integration/cli/commands/test_lock_resolve_auth.py
+++ b/tests/integration/cli/commands/test_lock_resolve_auth.py
@@ -168,7 +168,7 @@ def assert_unauthorized(
     assert (
         "There was 1 error downloading required artifacts:\n"
         "1. ansicolors 1.1.8 from {repo_url}/ansicolors-1.1.8-py2.py3-none-any.whl\n"
-        "    ERROR: Could not install requirement ansicolors==1.1.8 from "
+        "    pip: ERROR: Could not install requirement ansicolors==1.1.8 from "
         "{repo_url}/ansicolors-1.1.8-py2.py3-none-any.whl because of HTTP error 401 Client Error: "
         "Unauthorized for url: {repo_url}/ansicolors-1.1.8-py2.py3-none-any.whl for URL "
         "{repo_url}/ansicolors-1.1.8-py2.py3-none-any.whl".format(
diff --git a/tests/integration/cli/commands/test_lock_update_issues_2332_2334.py b/tests/integration/cli/commands/test_lock_update_issues_2332_2334.py
index 2635f03cf..e5e31a8b0 100644
--- a/tests/integration/cli/commands/test_lock_update_issues_2332_2334.py
+++ b/tests/integration/cli/commands/test_lock_update_issues_2332_2334.py
@@ -290,9 +290,9 @@ def test_lock_update_conflict(
                 else re.escape(
                     dedent(
                         """\
-                        The conflict is caused by:
-                             The user requested proj-b==1.*
-                             The user requested (constraint) proj-b>=2
+                        pip:  The conflict is caused by:
+                        pip:      The user requested proj-b==1.*
+                        pip:      The user requested (constraint) proj-b>=2
                         """
                     )
                 )
diff --git a/tests/integration/test_integration.py b/tests/integration/test_integration.py
index 15372960e..dce25e855 100644
--- a/tests/integration/test_integration.py
+++ b/tests/integration/test_integration.py
@@ -1753,24 +1753,24 @@ def test_pip_issues_9420_workaround():
     assert normalized_stderr.startswith(
         dedent(
             """\
-            ERROR: Cannot install colorama==0.4.1 and isort[colors]==5.7.0 because these package versions have conflicting dependencies.
-            ERROR: ResolutionImpossible: for help visit https://pip.pypa.io/
+            pip: ERROR: Cannot install colorama==0.4.1 and isort[colors]==5.7.0 because these package versions have conflicting dependencies.
+            pip: ERROR: ResolutionImpossible: for help visit https://pip.pypa.io/
             """
         ).strip()
     ), normalized_stderr
     assert normalized_stderr.endswith(
         dedent(
             """\
-            The conflict is caused by:
-            The user requested colorama==0.4.1
-            isort[colors] 5.7.0 depends on colorama<0.5.0 and >=0.4.3; extra == "colors"
-
-            To fix this you could try to:
-            1. loosen the range of package versions you've specified
-            2. remove package versions to allow pip to attempt to solve the dependency conflict
+            pip:  The conflict is caused by:
+            pip:      The user requested colorama==0.4.1
+            pip:      isort[colors] 5.7.0 depends on colorama<0.5.0 and >=0.4.3; extra == "colors"
+            pip:
+            pip:  To fix this you could try to:
+            pip:  1. loosen the range of package versions you've specified
+            pip:  2. remove package versions to allow pip to attempt to solve the dependency conflict
             """
         ).strip()
-    )
+    ), normalized_stderr
 
 
 @pytest.mark.skipif(
@@ -1970,30 +1970,30 @@ def test_require_hashes(tmpdir):
         re.sub(r"\s+", " ", line.strip()): index
         for index, line in enumerate(as_constraints_result.error.splitlines())
     }
-    index = error_lines["Expected sha512 worse"]
+    index = error_lines["pip: Expected sha512 worse"]
     assert (
         index + 1
         == error_lines[
-            "Got ca602ae6dd925648c8ff87ef00bcef2d0ebebf1090b44e8dd43b75403f07db50269e5078f709cbce8e"
-            "7cfaedaf1b754d02dda08b6970b6a157cbf4c31ebc16a7"
+            "pip: Got ca602ae6dd925648c8ff87ef00bcef2d0ebebf1090b44e8dd43b75403f07db50269e5078f709c"
+            "bce8e7cfaedaf1b754d02dda08b6970b6a157cbf4c31ebc16a7"
         ]
     )
 
-    index = error_lines["Expected sha384 bad"]
+    index = error_lines["pip: Expected sha384 bad"]
     assert (
         index + 1
         == error_lines[
-            "Got 64ec6b63f74b7bdf161a9b38fabf59c0a691ba9ed325f0864fea984e0deabe648cbd12d619d3989b64"
-            "24488349df3b30"
+            "pip: Got 64ec6b63f74b7bdf161a9b38fabf59c0a691ba9ed325f0864fea984e0deabe648cbd12d619d39"
+            "89b6424488349df3b30"
         ]
     )
 
     index = error_lines[
-        "Expected sha256 2f4da4594db7e1e110a944bb1b551fdf4e6c136ad42e4234131391e21eb5b0d0"
+        "pip: Expected sha256 2f4da4594db7e1e110a944bb1b551fdf4e6c136ad42e4234131391e21eb5b0d0"
     ]
     assert (
         index + 1
-        == error_lines["Got 2f4da4594db7e1e110a944bb1b551fdf4e6c136ad42e4234131391e21eb5b0df"]
+        == error_lines["pip: Got 2f4da4594db7e1e110a944bb1b551fdf4e6c136ad42e4234131391e21eb5b0df"]
     )
 
 
diff --git a/tests/integration/test_issue_2113.py b/tests/integration/test_issue_2113.py
new file mode 100644
index 000000000..39010adf8
--- /dev/null
+++ b/tests/integration/test_issue_2113.py
@@ -0,0 +1,181 @@
+# Copyright 2024 Pex project contributors.
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+from __future__ import absolute_import
+
+import os.path
+import re
+from textwrap import dedent
+
+import pytest
+
+from pex import targets
+from pex.build_system import pep_517
+from pex.common import safe_open
+from pex.resolve.configured_resolver import ConfiguredResolver
+from pex.result import try_
+from pex.typing import TYPE_CHECKING
+from testing import PY_VER, IntegResults, run_pex_command
+from testing.cli import run_pex3
+
+if TYPE_CHECKING:
+    from typing import Any
+
+
+@pytest.fixture
+def feast_simulator_project(tmpdir):
+    # type: (Any) -> str
+    project_dir = os.path.join(str(tmpdir), "feast-simulator")
+    with safe_open(os.path.join(project_dir, "setup.py"), "w") as fp:
+        fp.write(
+            dedent(
+                """\
+                from setuptools import setup
+
+
+                setup(
+                    name="feast-simulator",
+                    version="0.1.0",
+                    install_requires=["ansicolors<1.1.9,>=1.0.*"]
+                )
+                """
+            )
+        )
+    return project_dir
+
+
+skip_if_setuptools_too_old = pytest.mark.skipif(
+    PY_VER < (3, 7),
+    reason=(
+        "The setuptools / packaging compatible with Python<3.7 does not fail to process the bad "
+        "metadata used in this test."
+    ),
+)
+
+
+def assert_local_project_build_failure_message(result):
+    # type: (IntegResults) -> None
+    result.assert_failure(
+        expected_error_re=(
+            r".*"
+            r"^\s*pip:.*(?:{cause_distribution_hint_one}|{cause_distribution_hint_two}).*"
+            r"(?:{reason_one}|{reason_two}).*$"
+            r".*"
+            r"^\s*pip:.*{requirement}$"
+            r".*"
+        ).format(
+            # N.B.: We have two versions of cause and reason to account for permutations of Pip,
+            # setuptools and package resources messages which all intermix here.
+            cause_distribution_hint_one=re.escape(
+                "Failed to parse a requirement of feast-simulator 0.1.0"
+            ),
+            cause_distribution_hint_two=re.escape("error in feast-simulator setup command:"),
+            reason_one=re.escape(
+                "'install_requires' must be a string or list of strings containing valid "
+                "project/version requirement specifiers"
+            ),
+            reason_two=re.escape(".* suffix can only be used with `==` or `!=` operators"),
+            requirement=re.escape("ansicolors<1.1.9,>=1.0.*"),
+        ),
+        re_flags=re.DOTALL | re.MULTILINE,
+    )
+
+
+@skip_if_setuptools_too_old
+def test_metadata_gen_from_local_project_failure_lock(
+    tmpdir,  # type: Any
+    feast_simulator_project,  # type: str
+):
+    # type: (...) -> None
+    assert_local_project_build_failure_message(
+        run_pex3("lock", "create", feast_simulator_project, "-o", os.path.join(str(tmpdir), "lock"))
+    )
+
+
+@skip_if_setuptools_too_old
+def test_metadata_gen_from_local_project_failure_build_pex(
+    tmpdir,  # type: Any
+    feast_simulator_project,  # type: str
+):
+    # type: (...) -> None
+    assert_local_project_build_failure_message(
+        run_pex_command(
+            args=[feast_simulator_project, "-o", (os.path.join(str(tmpdir), "pex"))], quiet=True
+        )
+    )
+
+
+@pytest.fixture
+def feast_simulator_sdist(
+    tmpdir,  # type: Any
+    feast_simulator_project,  # type: str
+):
+    # type: (...) -> str
+    with safe_open(os.path.join(feast_simulator_project, "pyproject.toml"), "w") as fp:
+        fp.write(
+            dedent(
+                """\
+                [build-system]
+                build-backend = "setuptools.build_meta"
+
+                # N.B.: We need an older setuptools to be able to build an sdist containing bad
+                # metadata. With setuptools 67.0.0, packaging 23.0 is vendored with strict
+                # requirement parsing that leads to setuptools refusing to build the sdist at all.
+                # See: https://setuptools.pypa.io/en/stable/history.html#v67-0-0
+                requires = ["setuptools<67"]
+                """
+            )
+        )
+
+    return str(
+        try_(
+            pep_517.build_sdist(
+                project_directory=feast_simulator_project,
+                dist_dir=os.path.join(str(tmpdir), "build"),
+                target=targets.current(),
+                resolver=ConfiguredResolver.default(),
+            )
+        )
+    )
+
+
+def assert_dist_build_failure_message(result):
+    # type: (IntegResults) -> None
+    result.assert_failure(
+        expected_error_re=(
+            r".*"
+            r"^\s*pip:.*{cause_distribution_hint}.*$"
+            r".*"
+            r"^\s*pip:.*{reason}$"
+            r".*"
+            r"^\s*pip:.*{requirement}$"
+            r".*"
+        ).format(
+            cause_distribution_hint=re.escape("feast_simulator-0.1.0.dist-info"),
+            reason=re.escape(".* suffix can only be used with `==` or `!=` operators"),
+            requirement=re.escape("ansicolors<1.1.9,>=1.0.*"),
+        ),
+        re_flags=re.DOTALL | re.MULTILINE,
+    )
+
+
+@skip_if_setuptools_too_old
+def test_metadata_gen_from_dist_failure_lock(
+    tmpdir,  # type: Any
+    feast_simulator_sdist,  # type: str
+):
+    # type: (...) -> None
+    lock = os.path.join(str(tmpdir), "lock")
+    assert_dist_build_failure_message(run_pex3("lock", "create", feast_simulator_sdist, "-o", lock))
+
+
+@skip_if_setuptools_too_old
+def test_metadata_gen_from_dist_failure_build_pex(
+    tmpdir,  # type: Any
+    feast_simulator_sdist,  # type: str
+):
+    # type: (...) -> None
+    pex = os.path.join(str(tmpdir), "pex")
+    assert_dist_build_failure_message(
+        run_pex_command(args=[feast_simulator_sdist, "-o", pex], quiet=True)
+    )
diff --git a/tests/integration/test_pep_427.py b/tests/integration/test_pep_427.py
index 92b423b0f..b984717a0 100644
--- a/tests/integration/test_pep_427.py
+++ b/tests/integration/test_pep_427.py
@@ -10,6 +10,7 @@
 from pex.common import is_exe, safe_open
 from pex.pep_427 import install_wheel_interpreter
 from pex.pip.installation import get_pip
+from pex.resolve.configured_resolver import ConfiguredResolver
 from pex.typing import TYPE_CHECKING
 from pex.venv.virtualenv import InstallationChoice, Virtualenv
 from testing import WheelBuilder, make_env
@@ -27,12 +28,12 @@ def test_install_wheel_interpreter(tmpdir):
     assert not os.path.exists(cowsay_script)
 
     download_dir = os.path.join(str(tmpdir), "downloads")
-    get_pip().spawn_download_distributions(
+    get_pip(resolver=ConfiguredResolver.default()).spawn_download_distributions(
         download_dir=download_dir, requirements=["cowsay==5.0"]
     ).wait()
 
     wheel_dir = os.path.join(str(tmpdir), "wheels")
-    get_pip().spawn_build_wheels(
+    get_pip(resolver=ConfiguredResolver.default()).spawn_build_wheels(
         distributions=glob(os.path.join(download_dir, "*.tar.gz")), wheel_dir=wheel_dir
     ).wait()
     wheels = glob(os.path.join(wheel_dir, "*.whl"))
diff --git a/tests/pip/test_log_analyzer.py b/tests/pip/test_log_analyzer.py
new file mode 100644
index 000000000..03ac31305
--- /dev/null
+++ b/tests/pip/test_log_analyzer.py
@@ -0,0 +1,155 @@
+# Copyright 2024 Pex project contributors.
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+from __future__ import absolute_import
+
+import os.path
+import subprocess
+from textwrap import dedent
+
+import pytest
+
+from pex.common import chmod_plus_x
+from pex.jobs import Job
+from pex.pip.log_analyzer import ErrorAnalyzer, ErrorMessage, LogAnalyzer, LogScrapeJob
+from pex.typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from typing import Any, Optional
+
+    import attr  # vendor:skip
+else:
+    from pex.third_party import attr
+
+
+class NoopErrorAnalyzer(ErrorAnalyzer):
+    def analyze(self, line):
+        return self.Complete()
+
+
+@attr.s
+class FirstLineErrorAnalyzer(ErrorAnalyzer):
+    _error_message = attr.ib(default=None, init=False)  # type: Optional[ErrorMessage]
+
+    def analyze(self, line):
+        if self._error_message:
+            return self.Complete()
+        self._error_message = ErrorMessage(line)
+        return self.Continue(self._error_message)
+
+
+@pytest.fixture
+def log(tmpdir):
+    # type: (Any) -> str
+
+    log = os.path.join(str(tmpdir), "pip.log")
+    with open(log, "w") as fp:
+        fp.write(
+            dedent(
+                """\
+                Multi-line log output.
+                Line 2.
+                Key insight!
+                Line 4.
+                Last line.
+                """
+            )
+        )
+    return log
+
+
+@pytest.fixture
+def script(tmpdir):
+    # type: (Any) -> str
+
+    script = os.path.join(str(tmpdir), "exe.sh")
+    with open(script, "w") as fp:
+        fp.write(
+            dedent(
+                """\
+                #!/bin/sh
+
+                exit 42
+                """
+            )
+        )
+    chmod_plus_x(script)
+    return script
+
+
+def assert_job_failure(
+    log,  # type: str
+    script,  # type: str
+    *log_analyzers  # type: LogAnalyzer
+):
+    # type: (...) -> str
+
+    process = subprocess.Popen(args=[script])
+    process.wait()
+
+    finalized = []
+    with pytest.raises(Job.Error) as exc_info:
+        LogScrapeJob(
+            command=[script],
+            process=process,
+            log=log,
+            log_analyzers=log_analyzers,
+            preserve_log=False,
+            finalizer=lambda code: finalized.append(code),
+        ).wait()
+    assert not os.path.exists(log)
+    assert [42] == finalized
+    return str(exc_info.value)
+
+
+def test_errored_log_scrape_job_with_analysis(
+    tmpdir,  # type: Any
+    log,  # type: str
+    script,  # type: str
+):
+    # type: (...) -> None
+
+    error_msg = assert_job_failure(log, script, NoopErrorAnalyzer(), FirstLineErrorAnalyzer())
+    assert (
+        "pip: Executing {script} failed with 42\n"
+        "STDERR:\n"
+        "Multi-line log output.\n".format(script=script)
+    ) == error_msg
+
+
+def test_errored_log_scrape_job_with_no_analysis(
+    tmpdir,  # type: Any
+    log,  # type: str
+    script,  # type: str
+):
+    # type: (...) -> None
+
+    error_msg = assert_job_failure(log, script, NoopErrorAnalyzer())
+    assert (
+        "pip: Executing {script} failed with 42\n"
+        "STDERR:\n"
+        "Multi-line log output.\n"
+        "Line 2.\n"
+        "Key insight!\n"
+        "Line 4.\n"
+        "Last line.\n".format(script=script)
+    ) == error_msg
+
+
+def test_errored_log_scrape_job_with_no_analyzers(
+    tmpdir,  # type: Any
+    log,  # type: str
+    script,  # type: str
+):
+    # type: (...) -> None
+
+    error_msg = assert_job_failure(log, script)
+    assert (
+        "pip: Executing {script} failed with 42\n"
+        "STDERR:\n"
+        "Multi-line log output.\n"
+        "Line 2.\n"
+        "Key insight!\n"
+        "Line 4.\n"
+        "Last line.\n".format(script=script)
+    ) == error_msg
diff --git a/tests/test_dist_metadata.py b/tests/test_dist_metadata.py
index 2ad1fbcb7..4297e8150 100644
--- a/tests/test_dist_metadata.py
+++ b/tests/test_dist_metadata.py
@@ -28,6 +28,7 @@
 from pex.pep_503 import ProjectName
 from pex.pex_warnings import PEXWarning
 from pex.pip.installation import get_pip
+from pex.resolve.configured_resolver import ConfiguredResolver
 from pex.resolve.resolver_configuration import BuildConfiguration
 from pex.third_party.packaging.specifiers import SpecifierSet
 from pex.typing import TYPE_CHECKING
@@ -59,7 +60,7 @@ def downloaded_sdist(requirement):
     # type: (str) -> Iterator[str]
     with temporary_dir() as td:
         download_dir = os.path.join(td, "download")
-        get_pip().spawn_download_distributions(
+        get_pip(resolver=ConfiguredResolver.default()).spawn_download_distributions(
             download_dir=download_dir,
             requirements=[requirement],
             transitive=False,
@@ -103,7 +104,9 @@ def pip_tgz_sdist():
 def pip_wheel(pip_tgz_sdist):
     # type: (str) -> Iterator[str]
     with temporary_dir() as wheel_dir:
-        get_pip().spawn_build_wheels([pip_tgz_sdist], wheel_dir=wheel_dir).wait()
+        get_pip(resolver=ConfiguredResolver.default()).spawn_build_wheels(
+            [pip_tgz_sdist], wheel_dir=wheel_dir
+        ).wait()
         wheels = os.listdir(wheel_dir)
         assert len(wheels) == 1, "Expected 1 wheel to be built for {}.".format(pip_tgz_sdist)
         wheel = os.path.join(wheel_dir, wheels[0])
diff --git a/tests/test_jobs.py b/tests/test_jobs.py
index c10cb2103..7c460aaa8 100644
--- a/tests/test_jobs.py
+++ b/tests/test_jobs.py
@@ -1,6 +1,8 @@
 # Copyright 2019 Pex project contributors.
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
+from __future__ import absolute_import
+
 import json
 import os
 import subprocess
@@ -8,12 +10,12 @@
 
 import pytest
 
-from pex.interpreter import spawn_python_job
+from pex.interpreter import PythonInterpreter
 from pex.jobs import _ABSOLUTE_MAX_JOBS, DEFAULT_MAX_JOBS, Job, SpawnedJob, _sanitize_max_jobs
 from pex.typing import TYPE_CHECKING, cast
 
 if TYPE_CHECKING:
-    from typing import Any, Dict
+    from typing import Any, Dict, Iterable
 
 
 def test_sanitize_max_jobs_none():
@@ -40,6 +42,15 @@ def test_sanitize_max_jobs_too_large():
     assert _ABSOLUTE_MAX_JOBS == _sanitize_max_jobs(_ABSOLUTE_MAX_JOBS + 5)
 
 
+def spawn_python_job(
+    args,  # type: Iterable[str]
+    **subprocess_kwargs  # type: Any
+):
+    # type: (...) -> Job
+    cmd, process = PythonInterpreter.get().open_process(args=args, **subprocess_kwargs)
+    return Job(command=cmd, process=process)
+
+
 def create_error_job(exit_code):
     # type: (int) -> Job
     return spawn_python_job(args=["-c", "import sys; sys.exit({})".format(exit_code)])
diff --git a/tests/tools/commands/test_repository.py b/tests/tools/commands/test_repository.py
index 4a4b2629a..a164fd9a7 100644
--- a/tests/tools/commands/test_repository.py
+++ b/tests/tools/commands/test_repository.py
@@ -17,6 +17,7 @@
 from pex.dist_metadata import Distribution, Requirement
 from pex.pip.installation import get_pip
 from pex.pip.version import PipVersion
+from pex.resolve.configured_resolver import ConfiguredResolver
 from pex.resolve.resolver_configuration import BuildConfiguration
 from pex.third_party.packaging.specifiers import SpecifierSet
 from pex.typing import TYPE_CHECKING
@@ -218,7 +219,7 @@ def test_extract_lifecycle(pex, pex_tools_env, tmpdir):
     # Since we'll be locking down indexes to just find-links, we need to include the wheel .whl
     # needed by vendored Pip.
     vendored_pip_dists_dir = os.path.join(str(tmpdir), "vendored-pip-dists")
-    get_pip().spawn_download_distributions(
+    get_pip(resolver=ConfiguredResolver.default()).spawn_download_distributions(
         download_dir=vendored_pip_dists_dir,
         requirements=[PipVersion.VENDORED.wheel_requirement],
         build_configuration=BuildConfiguration.create(allow_builds=False),
diff --git a/tox.ini b/tox.ini
index 4664152f6..b318170ae 100644
--- a/tox.ini
+++ b/tox.ini
@@ -137,6 +137,9 @@ commands =
 
 [testenv:{typecheck,check}]
 deps =
+    # We keep this compatible with Python 2.7 for the 2.7 type check.
+    pytest==4.6.11
+
     # This version should track the version in pex/vendor/__init__.py.
     attrs @ git+https://github.com/python-attrs/attrs@947bfb542104209a587280701d8cb389c813459d
     httpx==0.23.0