diff --git a/src/serena/agent.py b/src/serena/agent.py
index 522b6c2..aa78640 100644
--- a/src/serena/agent.py
+++ b/src/serena/agent.py
@@ -865,7 +865,7 @@ class SerenaAgent:
         if len(relative_path.parts) > 0 and relative_path.parts[0] == ".git":
             return True
 
-        return match_path(str(relative_path), self.ignore_spec)
+        return match_path(str(relative_path), self.ignore_spec, root_path=self.get_project_root())
 
     def validate_relative_path(self, relative_path: str) -> None:
         """
diff --git a/src/serena/util/file_system.py b/src/serena/util/file_system.py
index f16b46a..26a5943 100644
--- a/src/serena/util/file_system.py
+++ b/src/serena/util/file_system.py
@@ -92,14 +92,14 @@ class GitignoreSpec:
         """Initialize the PathSpec from patterns."""
         self.pathspec = PathSpec.from_lines(pathspec.patterns.GitWildMatchPattern, self.patterns)
 
-    def matches(self, path: str) -> bool:
+    def matches(self, relative_path: str) -> bool:
         """
         Check if the given path matches any pattern in this gitignore spec.
 
-        :param path: Path to check (should be relative to repo root)
+        :param relative_path: Path to check (should be relative to repo root)
         :return: True if path matches any pattern
         """
-        return self.pathspec.match_file(path)
+        return match_path(relative_path, self.pathspec, root_path=os.path.dirname(self.file_path))
 
 
 class GitignoreParser:
@@ -276,7 +276,16 @@ class GitignoreParser:
         self._load_gitignore_files()
 
 
-def match_path(relative_path: str, path_spec: PathSpec) -> bool:
+def match_path(relative_path: str, path_spec: PathSpec, root_path: str = "") -> bool:
+    """
+    Match a relative path against a given pathspec. Just pathspec.match_file() is not enough,
+    we need to do some massaging to fix issues with pathspec matching.
+
+    :param relative_path: relative path to match against the pathspec
+    :param path_spec: the pathspec to match against
+    :param root_path: the root path from which the relative path is derived
+    :return:
+    """
     normalized_path = str(relative_path).replace(os.path.sep, "/")
 
     # We can have patterns like /src/..., which would only match corresponding paths from the repo root
@@ -289,6 +298,7 @@ def match_path(relative_path: str, path_spec: PathSpec) -> bool:
 
     # pathspec can't handle the matching of directories if they don't end with a slash!
     # see https://github.com/cpburnz/python-pathspec/issues/89
-    if os.path.isdir(relative_path) and not normalized_path.endswith("/"):
+    abs_path = os.path.abspath(os.path.join(root_path, relative_path))
+    if os.path.isdir(abs_path) and not normalized_path.endswith("/"):
         normalized_path = normalized_path + "/"
     return path_spec.match_file(normalized_path)
diff --git a/src/solidlsp/ls.py b/src/solidlsp/ls.py
index 77d35ba..4b8163c 100644
--- a/src/solidlsp/ls.py
+++ b/src/solidlsp/ls.py
@@ -318,7 +318,7 @@ class SolidLanguageServer(ABC):
             if self.is_ignored_dirname(part):
                 return True
 
-        return match_path(relative_path, self.get_ignore_spec())
+        return match_path(relative_path, self.get_ignore_spec(), root_path=self.repository_root_path)
 
     def _shutdown(self, timeout: float = 5.0):
         """