diff --git a/packages/griffelib/src/griffe/_internal/expressions.py b/packages/griffelib/src/griffe/_internal/expressions.py
index df959bee..e00bfe16 100644
--- a/packages/griffelib/src/griffe/_internal/expressions.py
+++ b/packages/griffelib/src/griffe/_internal/expressions.py
@@ -563,6 +563,43 @@ def iterate(self, *, flat: bool = True) -> Iterator[str | Expr]:
         yield "}"
 
 
+_FSTRING_ALL_QUOTES = ("'", '"', "'''", '"""')
+_FSTRING_MULTI_QUOTES = ('"""', "'''")
+
+
+def _fstring_choose_quote(values: Sequence[str | Expr]) -> tuple[str, list[str]]:
+    # Follows ast.unparse's visit_JoinedStr quote-selection algorithm.
+    # Pre-render all parts: literals get brace-doubled, expressions get flattened.
+    fstring_parts: list[tuple[str, bool]] = []
+    for value in values:
+        if isinstance(value, str):
+            fstring_parts.append((value.replace("{", "{{").replace("}", "}}"), True))
+        else:
+            fstring_parts.append((str(value), False))
+
+    quote_types: list[str] = list(_FSTRING_ALL_QUOTES)
+    escaped_parts: list[str] = []
+
+    for raw, is_constant in fstring_parts:
+        if is_constant:
+            escaped = (
+                raw.replace("\\", "\\\\")
+                .replace("\r", "\\r")
+                .replace("\0", "\\x00")
+                .replace("\n", "\\n")
+                .replace("\t", "\\t")
+            )
+            quote_types = [q for q in quote_types if q not in escaped] or quote_types
+            escaped_parts.append(escaped)
+        else:
+            if "\n" in raw:
+                quote_types = [q for q in quote_types if q in _FSTRING_MULTI_QUOTES] or quote_types
+            quote_types = [q for q in quote_types if q not in raw] or quote_types
+            escaped_parts.append(raw)
+
+    return quote_types[0], escaped_parts
+
+
 @dataclass(eq=True, slots=True)
 class ExprJoinedStr(Expr):
     """Joined strings like `f"a {b} c"`."""
@@ -571,9 +608,14 @@ class ExprJoinedStr(Expr):
     """Joined values."""
 
     def iterate(self, *, flat: bool = True) -> Iterator[str | Expr]:
-        yield "f'"
-        yield from _join(self.values, "", flat=flat)
-        yield "'"
+        quote, escaped_parts = _fstring_choose_quote(self.values)
+        yield f"f{quote}"
+        for value, escaped in zip(self.values, escaped_parts, strict=True):
+            if isinstance(value, str):
+                yield escaped
+            else:
+                yield from _yield(value, flat=flat, outer_precedence=_OperatorPrecedence.NONE)
+        yield quote
 
 
 @dataclass(eq=True, slots=True)
@@ -938,9 +980,14 @@ class ExprTemplateStr(Expr):
     """Joined values."""
 
     def iterate(self, *, flat: bool = True) -> Iterator[str | Expr]:
-        yield "t'"
-        yield from _join(self.values, "", flat=flat)
-        yield "'"
+        quote, escaped_parts = _fstring_choose_quote(self.values)
+        yield f"t{quote}"
+        for value, escaped in zip(self.values, escaped_parts, strict=True):
+            if isinstance(value, str):
+                yield escaped
+            else:
+                yield from _yield(value, flat=flat, outer_precedence=_OperatorPrecedence.NONE)
+        yield quote
 
 
 @dataclass(eq=True, slots=True)
@@ -1176,7 +1223,7 @@ def _build_constant(
         if in_joined_str and not in_formatted_str:
             # We're in a f-string, not in a formatted value, don't keep quotes.
             return node.value
-        if parse_strings and not literal_strings:
+        if parse_strings and not literal_strings and not in_formatted_str:
             # We're in a place where a string could be a type annotation
             # (and not in a Literal[...] type annotation).
             # We parse the string and build from the resulting nodes again.
diff --git a/packages/griffelib/tests/test_expressions.py b/packages/griffelib/tests/test_expressions.py
index 3fcd831b..dab89b81 100644
--- a/packages/griffelib/tests/test_expressions.py
+++ b/packages/griffelib/tests/test_expressions.py
@@ -233,6 +233,57 @@ def func[Z](arg1: T, arg2: Y): pass
         assert module["C.func"].parameters["arg2"].annotation.canonical_path == "Y"
 
 
+@pytest.mark.parametrize(
+    ("code", "expected"),
+    [
+        # Single quotes only in literal parts → double-quote delimiter.
+        ('f"it\'s {x}"', 'f"it\'s {x}"'),
+        ("f\"don't {x} won't {y}\"", "f\"don't {x} won't {y}\""),
+        # Double quotes only in literal parts → single-quote delimiter.
+        ("f'say \"hello\" to {x}'", "f'say \"hello\" to {x}'"),
+        ('f\'"open" and "close" around {x}\'', 'f\'"open" and "close" around {x}\''),
+        # Both quote types in literal parts → triple-single-quote delimiter.
+        (r"""f'it\'s "complicated" {x}'""", "f'''it's \"complicated\" {x}'''"),
+        (r"""f'she said "it\'s fine" to {x}'""", "f'''she said \"it's fine\" to {x}'''"),
+        (r"""f'can\'t stop, won\'t stop: "the {x} motto"'""", "f'''can't stop, won't stop: \"the {x} motto\"'''"),
+        # Literal braces must be doubled ({{/}}) in the output.
+        ("f'{a} {{b}}'", "f'{a} {{b}}'"),
+        ("f'{{opening}} {x} {{closing}}'", "f'{{opening}} {x} {{closing}}'"),
+        # String literals inside f-string expressions are never type annotations.
+        # The expression content drives delimiter choice (single → use double outer).
+        ("f'{print(\"1\")}'", "f\"{print('1')}\""),
+        ("f'{x + \"hello\"}'", "f\"{x + 'hello'}\""),
+    ],
+)
+def test_fstring_quote_selection(code: str, expected: str) -> None:
+    """ExprJoinedStr produces valid Python source for f-strings with tricky quote content.
+
+    Regression test for https://github.com/mkdocstrings/griffe/issues/444.
+    """
+    top_node = compile(code, filename="<>", mode="exec", flags=ast.PyCF_ONLY_AST, optimize=2)
+    expression = get_expression(top_node.body[0].value, parent=Module("module"))  # ty:ignore[unresolved-attribute]
+    assert str(expression) == expected
+
+
+@pytest.mark.skipif(sys.version_info < (3, 14), reason="t-strings require Python 3.14+")
+@pytest.mark.parametrize(
+    ("code", "expected"),
+    [
+        ('t"it\'s {x}"', 't"it\'s {x}"'),
+        ("t'say \"hello\" to {x}'", "t'say \"hello\" to {x}'"),
+        (r"""t'it\'s "complicated" {x}'""", "t'''it's \"complicated\" {x}'''"),
+    ],
+)
+def test_tstring_quote_selection(code: str, expected: str) -> None:
+    """ExprTemplateStr produces valid Python source for t-strings with tricky quote content.
+
+    Regression test for https://github.com/mkdocstrings/griffe/issues/444.
+    """
+    top_node = compile(code, filename="<>", mode="exec", flags=ast.PyCF_ONLY_AST, optimize=2)
+    expression = get_expression(top_node.body[0].value, parent=Module("module"))  # ty:ignore[unresolved-attribute]
+    assert str(expression) == expected
+
+
 def test_render_dict_comprehension() -> None:
     """Assert dict comprehensions are rendered correctly."""
     with temporary_visited_module(
diff --git a/packages/griffelib/tests/test_nodes.py b/packages/griffelib/tests/test_nodes.py
index 4e95d739..46d8d7b9 100644
--- a/packages/griffelib/tests/test_nodes.py
+++ b/packages/griffelib/tests/test_nodes.py
@@ -52,8 +52,20 @@
     "call(something=something)",
     # Strings.
     "f'a {round(key, 2)} {z}'",
-    # YORE: EOL 3.13: Replace line with `"t'a {round(key, 2)} {z}'",`.
+    'f"it\'s {x}"',  # ' only -> " delimiter
+    "f\"don't {x} won't {y}\"",  # multiple ' -> " delimiter
+    "f'say \"hello\" to {x}'",  # " only -> ' delimiter
+    'f\'"quoted" and "re-quoted" {x}\'',  # multiple " -> ' delimiter
+    "f'''it's \"complicated\" {x}'''",  # both -> triple-' delimiter
+    "f'''she said \"it's fine\" to {x}'''",  # both, different parts -> triple-'
+    # YORE: EOL 3.13: Regex-replace `\*\(\[(.+)\].+\),` with `\1,` within line.
     *(["t'a {round(key, 2)} {z}'"] if sys.version_info >= (3, 14) else []),
+    # YORE: EOL 3.13: Regex-replace `\*\(\[(.+)\].+\),` with `\1,` within line.
+    *(['t"it\'s {x}"'] if sys.version_info >= (3, 14) else []),
+    # YORE: EOL 3.13: Regex-replace `\*\(\[(.+)\].+\),` with `\1,` within line.
+    *(["t'say \"hello\" to {x}'"] if sys.version_info >= (3, 14) else []),
+    # YORE: EOL 3.13: Regex-replace `\*\(\[(.+)\].+\),` with `\1,` within line.
+    *(["t'''it's \"complicated\" {x}'''"] if sys.version_info >= (3, 14) else []),
     # Slices.
     "o[x]",
     "o[x, y]",