diff --git a/src/pip/_internal/build_env.py b/src/pip/_internal/build_env.py
index 3a246a1e349..98844e70287 100644
--- a/src/pip/_internal/build_env.py
+++ b/src/pip/_internal/build_env.py
@@ -169,10 +169,14 @@ def install(
             args.append("--prefer-binary")
         args.append("--")
         args.extend(requirements)
+
+        identify_requirement = (
+            f" for {for_req.name}" if for_req and for_req.name else ""
+        )
         with open_spinner(f"Installing {kind}") as spinner:
             call_subprocess(
                 args,
-                command_desc=f"pip subprocess to install {kind}",
+                command_desc=f"installing {kind}{identify_requirement}",
                 spinner=spinner,
             )
 
diff --git a/src/pip/_internal/exceptions.py b/src/pip/_internal/exceptions.py
index 98f95494c62..d6e9095fb55 100644
--- a/src/pip/_internal/exceptions.py
+++ b/src/pip/_internal/exceptions.py
@@ -190,6 +190,23 @@ class InstallationError(PipError):
     """General exception during installation"""
 
 
+class FailedToPrepareCandidate(InstallationError):
+    """Raised when we fail to prepare a candidate (i.e. fetch and generate metadata).
+
+    This is intentionally not a diagnostic error, since the output will be presented
+    above this error, when this occurs. This should instead present information to the
+    user.
+    """
+
+    def __init__(
+        self, *, package_name: str, requirement_chain: str, failed_step: str
+    ) -> None:
+        super().__init__(f"Failed to build '{package_name}' when {failed_step.lower()}")
+        self.package_name = package_name
+        self.requirement_chain = requirement_chain
+        self.failed_step = failed_step
+
+
 class MissingPyProjectBuildRequires(DiagnosticPipError):
     """Raised when pyproject.toml has `build-system`, but no `build-system.requires`."""
 
@@ -384,7 +401,7 @@ def __init__(
         output_lines: list[str] | None,
     ) -> None:
         if output_lines is None:
-            output_prompt = Text("See above for output.")
+            output_prompt = Text("No available output.")
         else:
             output_prompt = (
                 Text.from_markup(f"[red][{len(output_lines)} lines of output][/]\n")
@@ -412,7 +429,7 @@ def __str__(self) -> str:
         return f"{self.command_description} exited with {self.exit_code}"
 
 
-class MetadataGenerationFailed(InstallationSubprocessError, InstallationError):
+class MetadataGenerationFailed(DiagnosticPipError, InstallationError):
     reference = "metadata-generation-failed"
 
     def __init__(
@@ -420,7 +437,7 @@ def __init__(
         *,
         package_details: str,
     ) -> None:
-        super(InstallationSubprocessError, self).__init__(
+        super().__init__(
             message="Encountered error while generating package metadata.",
             context=escape(package_details),
             hint_stmt="See above for details.",
diff --git a/src/pip/_internal/resolution/resolvelib/candidates.py b/src/pip/_internal/resolution/resolvelib/candidates.py
index a8315349791..920eb1b9e2f 100644
--- a/src/pip/_internal/resolution/resolvelib/candidates.py
+++ b/src/pip/_internal/resolution/resolvelib/candidates.py
@@ -10,6 +10,7 @@
 from pip._vendor.packaging.version import Version
 
 from pip._internal.exceptions import (
+    FailedToPrepareCandidate,
     HashError,
     InstallationSubprocessError,
     InvalidInstalledPackage,
@@ -244,9 +245,19 @@ def _prepare(self) -> BaseDistribution:
             e.req = self._ireq
             raise
         except InstallationSubprocessError as exc:
-            # The output has been presented already, so don't duplicate it.
-            exc.context = "See above for output."
-            raise
+            if isinstance(self._ireq.comes_from, InstallRequirement):
+                request_chain = self._ireq.comes_from.from_path()
+            else:
+                request_chain = self._ireq.comes_from
+
+            if request_chain is None:
+                request_chain = "directly requested"
+
+            raise FailedToPrepareCandidate(
+                package_name=self._ireq.name or str(self._link),
+                requirement_chain=request_chain,
+                failed_step=exc.command_description,
+            )
 
         self._check_metadata_consistency(dist)
         return dist