diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7f7b9b04..e214da84 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,7 @@ Status of the `main` branch. Changes prior to the next official version change w
   - Add Grok Build support (context `grok`, setup CLI, hooks)
   - The `languages` key in project configurations was changed to `language_servers` to better reflect
     the actual semantics (configurations are automatically migrated)
+  - Fix: glob matching bare `*` and `?` in non-`**` patterns matched across `/`, contradicting documented behaviour #1732
 
 * Language Servers: 
   - Allow language server priorities to be configured in `serena_config.yml` (for auto-detection during 
diff --git a/src/serena/config/serena_config.py b/src/serena/config/serena_config.py
index 063cc658..9a169962 100644
--- a/src/serena/config/serena_config.py
+++ b/src/serena/config/serena_config.py
@@ -33,7 +33,7 @@ from serena.constants import (
     SERENA_MANAGED_DIR_NAME,
 )
 from serena.util.inspection import compute_language_server_support_composition
-from serena.util.text_utils import glob_match
+from serena.util.text_utils import GlobMatcher
 from serena.util.yaml import YamlCommentNormalisation, load_yaml, normalise_yaml_comments, save_yaml, transfer_yaml_comments
 from solidlsp.ls_config import LanguageServerId
 
@@ -1437,7 +1437,7 @@ class SerenaConfig(SharedConfig, ModeSelectionDefinitionWithBaseModes):
         """
         project_root_str = str(project_root)
         for pattern in self.trusted_project_path_patterns:
-            if glob_match(pattern, project_root_str):
+            if GlobMatcher(pattern).matches(project_root_str):
                 return True
         return False
 
diff --git a/src/serena/tools/file_tools.py b/src/serena/tools/file_tools.py
index 3cc55d82..bd52f5db 100644
--- a/src/serena/tools/file_tools.py
+++ b/src/serena/tools/file_tools.py
@@ -16,10 +16,9 @@ from serena.tools import SUCCESS_RESULT, EditedFileContext, EditingToolWithDiagn
 from serena.util.file_system import scan_directory
 from serena.util.text_utils import (
     ContentReplacer,
+    GlobMatcher,
     MultiFileContentReplacer,
     ReplacementOccurrence,
-    expand_braces,
-    glob_match,
 )
 from solidlsp.ls_utils import TextUtils
 
@@ -350,13 +349,13 @@ class ReplaceInFilesTool(EditingToolWithDiagnostics):
                 is_ignored_file=self.project.is_ignored_path,
                 relative_to=self.get_project_root(),
             )
-        include_patterns = expand_braces(paths_include_glob.strip()) if paths_include_glob.strip() else None
-        exclude_patterns = expand_braces(paths_exclude_glob.strip()) if paths_exclude_glob.strip() else None
+        include_glob_matcher = GlobMatcher(paths_include_glob.strip()) if paths_include_glob.strip() else None
+        exclude_glob_matcher = GlobMatcher(paths_exclude_glob.strip()) if paths_exclude_glob.strip() else None
         files: list[tuple[str, str]] = []
         for path in sorted(rel_paths):
-            if include_patterns and not any(glob_match(p, path) for p in include_patterns):
+            if include_glob_matcher and not include_glob_matcher.matches(path):
                 continue
-            if exclude_patterns and any(glob_match(p, path) for p in exclude_patterns):
+            if exclude_glob_matcher and exclude_glob_matcher.matches(path):
                 continue
             try:
                 files.append((path, self.project.read_file(path)))
diff --git a/src/serena/util/text_utils.py b/src/serena/util/text_utils.py
index 4f8f10cc..8ab6f943 100644
--- a/src/serena/util/text_utils.py
+++ b/src/serena/util/text_utils.py
@@ -1,4 +1,3 @@
-import fnmatch
 import hashlib
 import logging
 import re
@@ -9,6 +8,7 @@ from typing import Any, Literal, Self
 
 from bs4 import BeautifulSoup
 from joblib import Parallel, delayed
+from sensai.util.string import ToStringMixin
 
 from serena.util.file_proxy import FileCollection, FileProxy
 from solidlsp.ls_utils import TextUtils
@@ -116,34 +116,12 @@ class MatchedConsecutiveLines:
         return cls(lines=text_lines, source_file_path=source_file_path)
 
 
-def glob_to_regex(glob_pat: str) -> str:
-    regex_parts: list[str] = []
-    i = 0
-    while i < len(glob_pat):
-        ch = glob_pat[i]
-        if ch == "*":
-            regex_parts.append(".*")
-        elif ch == "?":
-            regex_parts.append(".")
-        elif ch == "\\":
-            i += 1
-            if i < len(glob_pat):
-                regex_parts.append(re.escape(glob_pat[i]))
-            else:
-                regex_parts.append("\\")
-        else:
-            regex_parts.append(re.escape(ch))
-        i += 1
-    return "".join(regex_parts)
-
-
 def search_text(
     pattern: str,
     content: str | None = None,
     source_file_path: str | None = None,
     context_lines_before: int = 0,
     context_lines_after: int = 0,
-    is_glob: bool = False,
     multiline: bool = True,
 ) -> list[MatchedConsecutiveLines]:
     """
@@ -155,8 +133,6 @@ def search_text(
         this has to be passed and the file will be read.
     :param context_lines_before: Number of context lines to include before matches
     :param context_lines_after: Number of context lines to include after matches
-    :param is_glob: If True, pattern is treated as a glob-like pattern (e.g., "*.py", "test_??.py")
-             and will be converted to regex internally
     :param multiline: whether to apply multi-line matching, enabling the flags re.DOTALL and re.MULTILINE
     :return: List of `TextSearchMatch` objects
     :raises: ValueError if the pattern is not valid
@@ -172,10 +148,6 @@ def search_text(
     lines = TextUtils.split_lines(content)
     total_lines = len(lines)
 
-    # Convert pattern to a compiled regex if it's a string
-    if is_glob:
-        pattern = glob_to_regex(pattern)
-
     # For multiline matches, optionally use DOTALL so '.' matches newlines
     flags = (re.MULTILINE | re.DOTALL) if multiline else 0
     compiled_pattern = re.compile(pattern, flags)
@@ -213,36 +185,9 @@ def search_text(
     return matches
 
 
-def expand_braces(pattern: str) -> list[str]:
+class GlobMatcher(ToStringMixin):
     """
-    Expands brace patterns in a glob string.
-    For example, "**/*.{js,jsx,ts,tsx}" becomes ["**/*.js", "**/*.jsx", "**/*.ts", "**/*.tsx"].
-    Handles multiple brace sets as well.
-    """
-    patterns = [pattern]
-    while any("{" in p or "}" in p for p in patterns):
-        new_patterns = []
-        for p in patterns:
-            match = re.search(r"\{([^{}]*)\}", p)
-            if match:
-                options_expr = match.group(1)
-                if not options_expr:
-                    raise ValueError(f"Invalid glob brace expression in {pattern!r}: empty braces are not allowed")
-
-                prefix = p[: match.start()]
-                suffix = p[match.end() :]
-                options = options_expr.split(",")
-                for option in options:
-                    new_patterns.append(f"{prefix}{option}{suffix}")
-            else:
-                raise ValueError(f"Invalid glob brace expression in {pattern!r}: unmatched brace")
-        patterns = new_patterns
-    return patterns
-
-
-def glob_match(pattern: str, path: str) -> bool:
-    """
-    Match a file path against a glob pattern.
+    Supports matching a file path against a glob pattern.
 
     Supports standard glob patterns:
     - * matches any number of characters except /
@@ -252,53 +197,100 @@ def glob_match(pattern: str, path: str) -> bool:
 
     Supports brace expansion:
     - {a,b,c} expands to multiple patterns (including nesting)
-
-    Unsupported patterns:
-    - Bash extended glob features are unavailable in Python's fnmatch
-    - Extended globs like !(), ?(), +(), *(), @() are not supported
-
-    :param pattern: Glob pattern (e.g., 'src/**/*.py', '**agent.py')
-    :param path: File path to match against
-    :return: True if path matches pattern
     """
-    pattern = pattern.replace("\\", "/")  # Normalize backslashes to forward slashes
-    path = path.replace("\\", "/")  # Normalize path backslashes to forward slashes
 
-    # Handle ** patterns that should match zero or more directories
-    if "**" in pattern:
-        # Method 1: Standard fnmatch (matches one or more directories)
-        regex1 = fnmatch.translate(pattern)
-        if re.match(regex1, path):
-            return True
-
-        # Method 2: Handle zero-directory case by removing /** entirely
-        # Convert "src/**/test.py" to "src/test.py"
-        if "/**/" in pattern:
-            zero_dir_pattern = pattern.replace("/**/", "/")
-            regex2 = fnmatch.translate(zero_dir_pattern)
-            if re.match(regex2, path):
-                return True
-
-        # Method 3: Handle leading ** case by removing **/
-        # Convert "**/test.py" to "test.py"
-        if pattern.startswith("**/"):
-            zero_dir_pattern = pattern[3:]  # Remove "**/"
-            regex3 = fnmatch.translate(zero_dir_pattern)
-            if re.match(regex3, path):
-                return True
-
-        return False
-    else:
-        # Simple pattern without **, use fnmatch directly
-        return fnmatch.fnmatch(path, pattern)
-
-
-class GlobMatcher:
     def __init__(self, expr: str):
-        self._patterns = expand_braces(expr)
+        """
+        :param expr: a glob pattern which may make use of brace expansion (e.g., "src/**/*.{js,jsx,ts,tsx}")
+        """
+        expr = expr.replace("\\", "/")  # normalise backslashes to forward slashes
+        self._glob_expr = expr
+        self._glob_patterns = self._expand_braces(expr)
+        self._regex_patterns = [re.compile(self._translate_glob_to_regex(p)) for p in self._glob_patterns]
+
+    def _tostring_includes(self) -> list[str]:
+        return ["_glob_expr"]
+
+    @staticmethod
+    def _expand_braces(pattern: str) -> list[str]:
+        """
+        Expands brace patterns in a glob string.
+        For example, "**/*.{js,jsx,ts,tsx}" becomes ["**/*.js", "**/*.jsx", "**/*.ts", "**/*.tsx"].
+        Handles multiple brace sets as well.
+        """
+        patterns = [pattern]
+        while any("{" in p or "}" in p for p in patterns):
+            new_patterns = []
+            for p in patterns:
+                match = re.search(r"\{([^{}]*)\}", p)
+                if match:
+                    options_expr = match.group(1)
+                    if not options_expr:
+                        raise ValueError(f"Invalid glob brace expression in {pattern!r}: empty braces are not allowed")
+
+                    prefix = p[: match.start()]
+                    suffix = p[match.end() :]
+                    options = options_expr.split(",")
+                    for option in options:
+                        new_patterns.append(f"{prefix}{option}{suffix}")
+                else:
+                    raise ValueError(f"Invalid glob brace expression in {pattern!r}: unmatched brace")
+            patterns = new_patterns
+        return patterns
+
+    @staticmethod
+    def _translate_glob_to_regex(pattern: str) -> str:
+        res = []
+        i = 0
+        n = len(pattern)
+        while i < n:
+            c = pattern[i]
+            i += 1
+            if c == "*":
+                if i < n and pattern[i] == "*":  # **
+                    i += 1
+                    if i < n and pattern[i] == "/":  # **/
+                        i += 1
+                        if res and res[-1] == "/":  # /**/
+                            res = res[:-1]
+                            res.append("(?:/|/.*/)")
+                        elif res:  # c**/ (with c != '/')
+                            res.append(".*/")
+                        else:  # **/ at the start of the pattern
+                            res.append("(?:.*/)?")
+                    else:  # c**d  (with c, d != '/')
+                        res.append(".*")
+                else:  # single *
+                    if not res or res[-1] != "[^/]*":
+                        res.append("[^/]*")
+            elif c == "?":
+                res.append("[^/]")
+            elif c == "[":
+                j = i
+                if j < n and pattern[j] == "!":
+                    j += 1
+                if j < n and pattern[j] == "]":
+                    j += 1
+                while j < n and pattern[j] != "]":
+                    j += 1
+                if j >= n:
+                    res.append(r"\[")
+                else:
+                    stuff = pattern[i:j]
+                    if stuff.startswith("!"):
+                        stuff = "^" + stuff[1:]
+                    elif stuff.startswith("^"):
+                        stuff = r"\^" + stuff
+                    res.append(f"[{stuff}]")
+                    i = j + 1
+            else:
+                res.append(re.escape(c))
+        inner = "".join(res)
+        return f"(?s:{inner})\\Z"
 
     def matches(self, path: str) -> bool:
-        return any(glob_match(p, path) for p in self._patterns)
+        path = path.replace("\\", "/")  # normalise backslashes to forward slashes
+        return any(regex.match(path) for regex in self._regex_patterns)
 
 
 def search_files(
diff --git a/test/serena/test_text_utils.py b/test/serena/test_text_utils.py
index 0eb86f3c..865b71b4 100644
--- a/test/serena/test_text_utils.py
+++ b/test/serena/test_text_utils.py
@@ -1,10 +1,9 @@
-import re
 from collections.abc import Callable
 
 import pytest
 
 from serena.util.file_proxy import FileCollection, FileProxy
-from serena.util.text_utils import LineType, MultiFileContentReplacer, glob_to_regex, search_files, search_text
+from serena.util.text_utils import GlobMatcher, LineType, MultiFileContentReplacer, search_files, search_text
 
 
 class TestSearchText:
@@ -177,94 +176,6 @@ class TestSearchText:
         match_lines = [line for line in multiline_match.lines if line.match_type == LineType.MATCH]
         assert len(match_lines) >= 3
 
-    def test_search_text_with_glob_pattern(self):
-        """Test searching with glob-like patterns."""
-        content = """
-        class UserService:
-            def get_user(self, user_id):
-                return {"id": user_id, "name": "Test User"}
-
-            def create_user(self, user_data):
-                print(f"Creating user: {user_data}")
-                return {"id": 123, **user_data}
-
-            def update_user(self, user_id, user_data):
-                print(f"Updating user {user_id} with {user_data}")
-                return True
-        """
-
-        # Search with a glob pattern for all user methods
-        matches = search_text("*_user*", content=content, is_glob=True, multiline=False)
-
-        assert len(matches) == 3
-        assert "get_user" in matches[0].lines[0].line_content
-        assert "create_user" in matches[1].lines[0].line_content
-        assert "update_user" in matches[2].lines[0].line_content
-
-    def test_search_text_with_complex_glob_pattern(self):
-        """Test searching with more complex glob patterns."""
-        content = """
-        def process_data(data):
-            return [transform(item) for item in data]
-
-        def transform(item):
-            if isinstance(item, dict):
-                return {k: v.upper() if isinstance(v, str) else v for k, v in item.items()}
-            elif isinstance(item, list):
-                return [x * 2 for x in item if isinstance(x, (int, float))]
-            elif isinstance(item, str):
-                return item.upper()
-            else:
-                return item
-        """
-
-        # Search with a simplified glob pattern to find all isinstance occurrences
-        matches = search_text("*isinstance*", content=content, is_glob=True, multiline=False)
-
-        # Should match lines with isinstance(item, dict) and isinstance(item, list)
-        assert len(matches) >= 2
-        instance_matches = [
-            line.line_content
-            for match in matches
-            for line in match.lines
-            if line.match_type == LineType.MATCH and "isinstance(item," in line.line_content
-        ]
-        assert len(instance_matches) >= 2
-        assert any("isinstance(item, dict)" in line for line in instance_matches)
-        assert any("isinstance(item, list)" in line for line in instance_matches)
-
-    def test_search_text_glob_with_special_chars(self):
-        """Glob patterns containing regex special characters should match literally."""
-        content = """
-        def func_square():
-            print("value[42]")
-
-        def func_curly():
-            print("value{bar}")
-        """
-
-        matches_square = search_text(r"*\[42\]*", content=content, is_glob=True, multiline=False)
-        assert len(matches_square) == 1
-        assert "[42]" in matches_square[0].lines[0].line_content
-
-        matches_curly = search_text("*{bar}*", content=content, is_glob=True, multiline=False)
-        assert len(matches_curly) == 1
-        assert "{bar}" in matches_curly[0].lines[0].line_content
-
-    def test_glob_to_regex_question_matches_single_char(self):
-        """A glob '?' matches exactly one character, matching glob_match's documented semantics."""
-        rx = glob_to_regex("a?c")
-        assert re.fullmatch(rx, "abc") is not None
-        assert re.fullmatch(rx, "ac") is None
-        assert re.fullmatch(rx, "abbc") is None
-
-    def test_search_text_glob_question_single_char(self):
-        """search_text('c?t', is_glob=True) must match 'cat' (one char), not 'coat' (two chars)."""
-        content = "value_cat_end\nvalue_coat_end"
-        matches = search_text("c?t", content=content, is_glob=True, multiline=False)
-        assert len(matches) == 1
-        assert "value_cat_end" in matches[0].lines[0].line_content
-
     def test_search_text_no_matches(self):
         """Test searching with a pattern that doesn't match anything."""
         content = """
@@ -317,7 +228,8 @@ class TestSearchFiles:
             (["a.py", "b.txt", "c.py"], "match", "*.py", "c.*", ["a.py"], "Include .py, exclude c.*"),
             # Directory matching - Using pathspec patterns
             (["main.c", "test/main.c"], "match", "test/*", None, ["test/main.c"], "Include files in test/ subdir"),
-            (["data/a.csv", "data/b.log"], "match", "data/*", "*.log", ["data/a.csv"], "Include data/*, exclude *.log"),
+            # A bare `*.log` no longer crosses `/` (see #1732); use `data/*.log` to exclude within data/.
+            (["data/a.csv", "data/b.log"], "match", "data/*", "data/*.log", ["data/a.csv"], "Include data/*, exclude data/*.log"),
             (["src/a.py", "tests/b.py"], "match", "src/**", "tests/**", ["src/a.py"], "Include src/**, exclude tests/**"),
             (["src/mod/a.py", "tests/b.py"], "match", "**/*.py", "tests/**", ["src/mod/a.py"], "Include **/*.py, exclude tests/**"),
             (["file.py", "dir/file.py"], "match", "dir/*.py", None, ["dir/file.py"], "Include files directly in dir"),
@@ -593,23 +505,33 @@ class TestGlobMatch:
         [
             # Basic wildcard patterns
             ("*.py", "file.py", True),
+            ("*.py", "src/file.py", False),
             ("*.py", "file.txt", False),
             ("*agent.py", "agent.py", True),
             ("*agent.py", "process_isolated_agent.py", True),
+            ("*agent.py", "src/agent.py", False),
             ("*agent.py", "agent_test.py", False),
+            ("a?b.py", "acb.py", True),
+            ("a?b.py", "a/b.py", False),
+            ("src/*.py", "src/file.py", True),
+            ("src/*.py", "src/sub/file.py", False),
             # Double asterisk patterns
             ("**agent.py", "agent.py", True),
+            ("**/agent.py", "agent.py", True),
+            ("**/agent.py", "src/serena/agent.py", True),
+            ("src/**/agent.py", "src/agent.py", True),
+            ("src/**/agent.py", "src/serena/foo/agent.py", True),
+            ("src/s**a/agent.py", "src/serena/agent.py", True),
+            ("src/s**a/agent.py", "src/serena/a/agent.py", True),
             ("**agent.py", "src/agent.py", True),
             ("**agent.py", "src/serena/agent.py", True),
             ("**agent.py", "src/serena/process_isolated_agent.py", True),
             ("**agent.py", "agent_test.py", False),
-            # Prefix with double asterisk
             ("src/**agent.py", "src/agent.py", True),
             ("src/**agent.py", "src/serena/agent.py", True),
             ("src/**agent.py", "src/serena/process_isolated_agent.py", True),
             ("src/**agent.py", "other/agent.py", False),
             ("src/**agent.py", "src/agent_test.py", False),
-            # Directory patterns
             ("src/**", "src/file.py", True),
             ("src/**", "src/dir/file.py", True),
             ("src/**", "other/file.py", False),
@@ -620,13 +542,20 @@ class TestGlobMatch:
             # Simple patterns without asterisks
             ("src/file.py", "src/file.py", True),
             ("src/file.py", "src/other.py", False),
+            # Patterns with backslash
+            ("src\\file.py", "src/file.py", True),
+            ("src\\file.py", "src\\file.py", True),
+            ("src\\file.py", "src/other.py", False),
+            # Patterns with []
+            ("file[0-9].py", "file1.py", True),
+            ("file[0-9].py", "filea.py", False),
+            ("file[!0-9].py", "filea.py", True),
+            ("file[!0-9].py", "file1.py", False),
         ],
     )
     def test_glob_match(self, pattern, path, expected):
         """Test glob_match function with various patterns."""
-        from serena.util.text_utils import glob_match
-
-        assert glob_match(pattern, path) == expected
+        assert GlobMatcher(pattern).matches(path) == expected
 
 
 class TestExpandBraces:
@@ -651,9 +580,7 @@ class TestExpandBraces:
     )
     def test_expand_braces(self, pattern, expected):
         """Test brace expansion for glob patterns."""
-        from serena.util.text_utils import expand_braces
-
-        assert sorted(expand_braces(pattern)) == sorted(expected)
+        assert sorted(GlobMatcher._expand_braces(pattern)) == sorted(expected)
 
     @pytest.mark.parametrize(
         "pattern",
@@ -665,10 +592,8 @@ class TestExpandBraces:
     )
     def test_expand_braces_rejects_malformed_braces(self, pattern):
         """Malformed brace globs should fail instead of looping forever."""
-        from serena.util.text_utils import expand_braces
-
         with pytest.raises(ValueError, match="Invalid glob brace expression"):
-            expand_braces(pattern)
+            GlobMatcher._expand_braces(pattern)
 
 
 class TestMultiFileContentReplacer: