diff --git a/openapi_core/spec/paths.py b/openapi_core/spec/paths.py
index f6e8228a..3d441de0 100644
--- a/openapi_core/spec/paths.py
+++ b/openapi_core/spec/paths.py
@@ -62,3 +62,14 @@ def from_dict(
             ref_resolver_handlers=ref_resolver_handlers,
             separator=separator,
         )
+
+    def exists(self) -> bool:
+        try:
+            self.content()
+        except KeyError:
+            return False
+        else:
+            return True
+
+    def uri(self) -> str:
+        return f"#/{str(self)}"
diff --git a/openapi_core/templating/paths/exceptions.py b/openapi_core/templating/paths/exceptions.py
index 4e38c480..8eccde4a 100644
--- a/openapi_core/templating/paths/exceptions.py
+++ b/openapi_core/templating/paths/exceptions.py
@@ -9,7 +9,7 @@ class PathError(OpenAPIError):
 
 @dataclass
 class PathNotFound(PathError):
-    """Find path error"""
+    """Path not found"""
 
     url: str
 
@@ -17,6 +17,14 @@ def __str__(self) -> str:
         return f"Path not found for {self.url}"
 
 
+@dataclass
+class PathsNotFound(PathNotFound):
+    """Paths not found"""
+
+    def __str__(self) -> str:
+        return f"Paths not found in spec: {self.url}"
+
+
 @dataclass
 class OperationNotFound(PathError):
     """Find path operation error"""
diff --git a/openapi_core/templating/paths/finders.py b/openapi_core/templating/paths/finders.py
index f4c9cb04..e6f70841 100644
--- a/openapi_core/templating/paths/finders.py
+++ b/openapi_core/templating/paths/finders.py
@@ -15,6 +15,7 @@
 from openapi_core.templating.paths.datatypes import PathOperationServer
 from openapi_core.templating.paths.exceptions import OperationNotFound
 from openapi_core.templating.paths.exceptions import PathNotFound
+from openapi_core.templating.paths.exceptions import PathsNotFound
 from openapi_core.templating.paths.exceptions import ServerNotFound
 from openapi_core.templating.paths.util import template_path_len
 from openapi_core.templating.util import parse
@@ -73,8 +74,10 @@ def __init__(self, spec: Spec, base_url: Optional[str] = None):
         self.base_url = base_url
 
     def _get_paths_iter(self, name: str) -> Iterator[Path]:
-        template_paths: List[Path] = []
         paths = self.spec / "paths"
+        if not paths.exists():
+            raise PathsNotFound(paths.uri())
+        template_paths: List[Path] = []
         for path_pattern, path in list(paths.items()):
             # simple path.
             # Return right away since it is always the most concrete
@@ -140,9 +143,9 @@ def _get_servers_iter(
 
 class WebhookPathFinder(BasePathFinder):
     def _get_paths_iter(self, name: str) -> Iterator[Path]:
-        if "webhooks" not in self.spec:
-            raise PathNotFound("Webhooks not found")
         webhooks = self.spec / "webhooks"
+        if not webhooks.exists():
+            raise PathsNotFound(webhooks.uri())
         for webhook_name, path in list(webhooks.items()):
             if name == webhook_name:
                 path_result = TemplateResult(webhook_name, {})
diff --git a/tests/unit/templating/test_paths_finders.py b/tests/unit/templating/test_paths_finders.py
index 5c3fd065..13240112 100644
--- a/tests/unit/templating/test_paths_finders.py
+++ b/tests/unit/templating/test_paths_finders.py
@@ -4,6 +4,7 @@
 from openapi_core.templating.datatypes import TemplateResult
 from openapi_core.templating.paths.exceptions import OperationNotFound
 from openapi_core.templating.paths.exceptions import PathNotFound
+from openapi_core.templating.paths.exceptions import PathsNotFound
 from openapi_core.templating.paths.exceptions import ServerNotFound
 from openapi_core.templating.paths.finders import APICallPathFinder
 from openapi_core.testing import MockRequest
@@ -272,6 +273,22 @@ def test_raises(self, finder):
             finder.find(method, full_url)
 
 
+class BaseTestPathsNotFound:
+    @pytest.fixture
+    def spec(self, info):
+        spec = {
+            "info": info,
+        }
+        return Spec.from_dict(spec, validator=None)
+
+    def test_raises(self, finder):
+        method = "get"
+        full_url = "http://petstore.swagger.io/resource"
+
+        with pytest.raises(PathsNotFound):
+            finder.find(method, full_url)
+
+
 class TestSpecSimpleServerServerNotFound(
     BaseTestServerNotFound,
     BaseTestSpecServer,
@@ -299,6 +316,14 @@ class TestSpecSimpleServerPathNotFound(
     pass
 
 
+class TestSpecSimpleServerPathsNotFound(
+    BaseTestPathsNotFound,
+    BaseTestSpecServer,
+    BaseTestSimpleServer,
+):
+    pass
+
+
 class TestOperationSimpleServerServerNotFound(
     BaseTestServerNotFound,
     BaseTestOperationServer,
@@ -326,6 +351,14 @@ class TestOperationSimpleServerPathNotFound(
     pass
 
 
+class TestOperationSimpleServerPathsNotFound(
+    BaseTestPathsNotFound,
+    BaseTestOperationServer,
+    BaseTestSimpleServer,
+):
+    pass
+
+
 class TestPathSimpleServerServerNotFound(
     BaseTestServerNotFound,
     BaseTestPathServer,
@@ -353,6 +386,14 @@ class TestPathSimpleServerPathNotFound(
     pass
 
 
+class TestPathSimpleServerPathsNotFound(
+    BaseTestPathsNotFound,
+    BaseTestPathServer,
+    BaseTestSimpleServer,
+):
+    pass
+
+
 class TestSpecSimpleServerValid(
     BaseTestValid, BaseTestSpecServer, BaseTestSimplePath, BaseTestSimpleServer
 ):
@@ -428,6 +469,14 @@ class TestSpecVariableServerPathNotFound(
     pass
 
 
+class TestSpecVariableServerPathsNotFound(
+    BaseTestPathsNotFound,
+    BaseTestSpecServer,
+    BaseTestVariableServer,
+):
+    pass
+
+
 class TestOperationVariableServerServerNotFound(
     BaseTestServerNotFound,
     BaseTestOperationServer,
@@ -455,6 +504,14 @@ class TestOperationVariableServerPathNotFound(
     pass
 
 
+class TestOperationVariableServerPathsNotFound(
+    BaseTestPathsNotFound,
+    BaseTestOperationServer,
+    BaseTestVariableServer,
+):
+    pass
+
+
 class TestPathVariableServerServerNotFound(
     BaseTestServerNotFound,
     BaseTestPathServer,
@@ -482,6 +539,14 @@ class TestPathVariableServerPathNotFound(
     pass
 
 
+class TestPathVariableServerPathsNotFound(
+    BaseTestPathsNotFound,
+    BaseTestPathServer,
+    BaseTestVariableServer,
+):
+    pass
+
+
 class TestSpecVariableServerValid(
     BaseTestVariableValid,
     BaseTestSpecServer,