diff --git a/docs/changelog/3578.bugfix.rst b/docs/changelog/3578.bugfix.rst
new file mode 100644
index 0000000000..236ab29210
--- /dev/null
+++ b/docs/changelog/3578.bugfix.rst
@@ -0,0 +1,2 @@
+Makes the error message more clear when pyproject.toml file cannot be loaded
+or is missing expected keys.
diff --git a/src/tox/config/source/discover.py b/src/tox/config/source/discover.py
index f04b9a7a0c..988c4976da 100644
--- a/src/tox/config/source/discover.py
+++ b/src/tox/config/source/discover.py
@@ -5,6 +5,7 @@
 from pathlib import Path
 from typing import TYPE_CHECKING
 
+from tox.config.types import MissingRequiredConfigKeyError
 from tox.report import HandledError
 
 from .legacy_toml import LegacyToml
@@ -59,21 +60,32 @@ def _locate_source() -> Source | None:
     for base in chain([folder], folder.parents):
         for src_type in SOURCE_TYPES:
             candidate: Path = base / src_type.FILENAME
-            try:
-                return src_type(candidate)
-            except ValueError:
-                pass
+            if candidate.exists():
+                try:
+                    return src_type(candidate)
+                except MissingRequiredConfigKeyError as exc:
+                    msg = f"{src_type.__name__} skipped loading {candidate.resolve()} due to {exc}"
+                    logging.info(msg)
+                except ValueError as exc:
+                    msg = f"{src_type.__name__} failed loading {candidate.resolve()} due to {exc}"
+                    raise HandledError(msg) from exc
     return None
 
 
 def _load_exact_source(config_file: Path) -> Source:
     # if the filename matches to the letter some config file name do not fallback to other source types
+    if not config_file.exists():
+        msg = f"config file {config_file} does not exist"
+        raise HandledError(msg)
     exact_match = [s for s in SOURCE_TYPES if config_file.name == s.FILENAME]  # pragma: no cover
     for src_type in exact_match or SOURCE_TYPES:  # pragma: no branch
         try:
             return src_type(config_file)
-        except ValueError:  # noqa: PERF203
+        except MissingRequiredConfigKeyError:  # noqa: PERF203
             pass
+        except ValueError as exc:
+            msg = f"{src_type.__name__} failed loading {config_file.resolve()} due to {exc}"
+            raise HandledError(msg) from exc
     msg = f"could not recognize config file {config_file}"
     raise HandledError(msg)
 
@@ -88,7 +100,7 @@ def _create_default_source(root_dir: Path | None) -> Source:
     else:  # if not set use where we find pyproject.toml in the tree or cwd
         empty = root_dir
     names = " or ".join({i.FILENAME: None for i in SOURCE_TYPES})
-    logging.warning("No %s found, assuming empty tox.ini at %s", names, empty)
+    logging.warning("No loadable %s found, assuming empty tox.ini at %s", names, empty)
     return ToxIni(empty / "tox.ini", content="")
 
 
diff --git a/src/tox/config/source/legacy_toml.py b/src/tox/config/source/legacy_toml.py
index db6227cddd..6de39f11fe 100644
--- a/src/tox/config/source/legacy_toml.py
+++ b/src/tox/config/source/legacy_toml.py
@@ -2,6 +2,8 @@
 
 import sys
 
+from tox.config.types import MissingRequiredConfigKeyError
+
 if sys.version_info >= (3, 11):  # pragma: no cover (py311+)
     import tomllib
 else:  # pragma: no cover (py311+)
@@ -27,7 +29,8 @@ def __init__(self, path: Path) -> None:
         try:
             content = toml_content["tool"]["tox"]["legacy_tox_ini"]
         except KeyError as exc:
-            raise ValueError(path) from exc
+            msg = f"`tool.tox.legacy_tox_ini` missing from {path}"
+            raise MissingRequiredConfigKeyError(msg) from exc
         super().__init__(path, content=content)
 
 
diff --git a/src/tox/config/source/setup_cfg.py b/src/tox/config/source/setup_cfg.py
index d1d316eac9..ffb994afdd 100644
--- a/src/tox/config/source/setup_cfg.py
+++ b/src/tox/config/source/setup_cfg.py
@@ -18,7 +18,8 @@ class SetupCfg(IniSource):
     def __init__(self, path: Path) -> None:
         super().__init__(path)
         if not self._parser.has_section(self.CORE_SECTION.key):
-            raise ValueError
+            msg = f"section {self.CORE_SECTION.key} not found"
+            raise ValueError(msg)
 
 
 __all__ = ("SetupCfg",)
diff --git a/src/tox/config/source/toml_pyproject.py b/src/tox/config/source/toml_pyproject.py
index 4c03e41ac6..b70b1404b3 100644
--- a/src/tox/config/source/toml_pyproject.py
+++ b/src/tox/config/source/toml_pyproject.py
@@ -7,6 +7,7 @@
 
 from tox.config.loader.section import Section
 from tox.config.loader.toml import TomlLoader
+from tox.config.types import MissingRequiredConfigKeyError
 from tox.report import HandledError
 
 from .api import Source
@@ -81,7 +82,7 @@ def __init__(self, path: Path) -> None:
                 our_content = our_content[key]
             self._our_content = our_content
         except KeyError as exc:
-            raise ValueError(path) from exc
+            raise MissingRequiredConfigKeyError(path) from exc
         super().__init__(path)
 
     def get_core_section(self) -> Section:
diff --git a/src/tox/config/types.py b/src/tox/config/types.py
index 42c2c48149..0e9070ad40 100644
--- a/src/tox/config/types.py
+++ b/src/tox/config/types.py
@@ -10,6 +10,13 @@ class CircularChainError(ValueError):
     """circular chain in config"""
 
 
+class MissingRequiredConfigKeyError(ValueError):
+    """missing required config key
+
+    Used by the two toml loaders in order to identify if config keys are present.
+    """
+
+
 class Command:  # noqa: PLW1641
     """A command to execute."""
 
diff --git a/tests/config/source/test_discover.py b/tests/config/source/test_discover.py
index 86370e5cec..d86fb750bc 100644
--- a/tests/config/source/test_discover.py
+++ b/tests/config/source/test_discover.py
@@ -10,8 +10,8 @@
 
 def out_no_src(path: Path) -> str:
     return (
-        f"ROOT: No tox.ini or setup.cfg or pyproject.toml or tox.toml found, assuming empty tox.ini at {path}\n"
-        f"default environments:\npy -> [no description]\n"
+        f"ROOT: No loadable tox.ini or setup.cfg or pyproject.toml or tox.toml found, assuming empty tox.ini at {path}"
+        f"\ndefault environments:\npy -> [no description]\n"
     )
 
 
@@ -47,4 +47,4 @@ def test_bad_src_content(tox_project: ToxProjectCreator, tmp_path: Path) -> None
 
     outcome = project.run("l", "-c", str(tmp_path / "setup.cfg"))
     outcome.assert_failed()
-    assert outcome.out == f"ROOT: HandledError| could not recognize config file {tmp_path / 'setup.cfg'}\n"
+    assert outcome.out == f"ROOT: HandledError| config file {tmp_path / 'setup.cfg'} does not exist\n"
diff --git a/tests/config/source/test_setup_cfg.py b/tests/config/source/test_setup_cfg.py
index 3de4747353..e5a84ec9d4 100644
--- a/tests/config/source/test_setup_cfg.py
+++ b/tests/config/source/test_setup_cfg.py
@@ -19,4 +19,4 @@ def test_bad_conf_setup_cfg(tox_project: ToxProjectCreator) -> None:
     filename = str(project.path / "setup.cfg")
     outcome = project.run("l", "-c", filename)
     outcome.assert_failed()
-    assert outcome.out == f"ROOT: HandledError| could not recognize config file {filename}\n"
+    assert outcome.out == f"ROOT: HandledError| SetupCfg failed loading {filename} due to section tox:tox not found\n"
diff --git a/tests/session/cmd/test_legacy.py b/tests/session/cmd/test_legacy.py
index 0d04dc6a12..08d65fe2d5 100644
--- a/tests/session/cmd/test_legacy.py
+++ b/tests/session/cmd/test_legacy.py
@@ -66,7 +66,8 @@ def test_legacy_list_env_with_no_tox_file(tox_project: ToxProjectCreator) -> Non
     outcome = project.run("le", "-l")
     outcome.assert_success()
     out = (
-        f"ROOT: No tox.ini or setup.cfg or pyproject.toml or tox.toml found, assuming empty tox.ini at {project.path}\n"
+        "ROOT: No loadable tox.ini or setup.cfg or pyproject.toml or tox.toml found, assuming empty tox.ini at "
+        f"{project.path}\n"
     )
     assert not outcome.err
     assert outcome.out == out