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[pre-commit.ci] pre-commit autoupdate (#3915)
[etc/vim.git] / src / black / trans.py
index 055f33c0ee2fda2d8c52a286e3bc807f5647798c..c0cc92613acba59996d25dba09701f2137a10985 100644 (file)
@@ -1,39 +1,57 @@
 """
 String transformers that can split and merge strings.
 """
+import re
 from abc import ABC, abstractmethod
 from collections import defaultdict
 from dataclasses import dataclass
-import regex as re
 from typing import (
     Any,
     Callable,
+    ClassVar,
     Collection,
     Dict,
+    Final,
     Iterable,
     Iterator,
     List,
+    Literal,
     Optional,
     Sequence,
+    Set,
     Tuple,
     TypeVar,
     Union,
 )
 
-from black.rusty import Result, Ok, Err
+from mypy_extensions import trait
 
-from black.mode import Feature
-from black.nodes import syms, replace_child, parent_type
-from black.nodes import is_empty_par, is_empty_lpar, is_empty_rpar
-from black.nodes import CLOSING_BRACKETS, STANDALONE_COMMENT
-from black.lines import Line, append_leaves
-from black.brackets import BracketMatchError
 from black.comments import contains_pragma_comment
-from black.strings import has_triple_quotes, get_string_prefix, assert_is_leaf_string
-from black.strings import normalize_string_quotes
-
-from blib2to3.pytree import Leaf, Node
+from black.lines import Line, append_leaves
+from black.mode import Feature, Mode
+from black.nodes import (
+    CLOSING_BRACKETS,
+    OPENING_BRACKETS,
+    STANDALONE_COMMENT,
+    is_empty_lpar,
+    is_empty_par,
+    is_empty_rpar,
+    is_part_of_annotation,
+    parent_type,
+    replace_child,
+    syms,
+)
+from black.rusty import Err, Ok, Result
+from black.strings import (
+    assert_is_leaf_string,
+    count_chars_in_width,
+    get_string_prefix,
+    has_triple_quotes,
+    normalize_string_quotes,
+    str_width,
+)
 from blib2to3.pgen2 import token
+from blib2to3.pytree import Leaf, Node
 
 
 class CannotTransform(Exception):
@@ -43,13 +61,15 @@ class CannotTransform(Exception):
 # types
 T = TypeVar("T")
 LN = Union[Leaf, Node]
-Transformer = Callable[[Line, Collection[Feature]], Iterator[Line]]
+Transformer = Callable[[Line, Collection[Feature], Mode], Iterator[Line]]
 Index = int
 NodeType = int
 ParserState = int
 StringID = int
 TResult = Result[T, CannotTransform]  # (T)ransform Result
-TMatchResult = TResult[Index]
+TMatchResult = TResult[List[Index]]
+
+SPLIT_SAFE_CHARS = frozenset(["\u3001", "\u3002", "\uff0c"])  # East Asian stops
 
 
 def TErr(err_msg: str) -> Err[CannotTransform]:
@@ -61,7 +81,86 @@ def TErr(err_msg: str) -> Err[CannotTransform]:
     return Err(cant_transform)
 
 
-@dataclass  # type: ignore
+def hug_power_op(
+    line: Line, features: Collection[Feature], mode: Mode
+) -> Iterator[Line]:
+    """A transformer which normalizes spacing around power operators."""
+
+    # Performance optimization to avoid unnecessary Leaf clones and other ops.
+    for leaf in line.leaves:
+        if leaf.type == token.DOUBLESTAR:
+            break
+    else:
+        raise CannotTransform("No doublestar token was found in the line.")
+
+    def is_simple_lookup(index: int, step: Literal[1, -1]) -> bool:
+        # Brackets and parentheses indicate calls, subscripts, etc. ...
+        # basically stuff that doesn't count as "simple". Only a NAME lookup
+        # or dotted lookup (eg. NAME.NAME) is OK.
+        if step == -1:
+            disallowed = {token.RPAR, token.RSQB}
+        else:
+            disallowed = {token.LPAR, token.LSQB}
+
+        while 0 <= index < len(line.leaves):
+            current = line.leaves[index]
+            if current.type in disallowed:
+                return False
+            if current.type not in {token.NAME, token.DOT} or current.value == "for":
+                # If the current token isn't disallowed, we'll assume this is simple as
+                # only the disallowed tokens are semantically attached to this lookup
+                # expression we're checking. Also, stop early if we hit the 'for' bit
+                # of a comprehension.
+                return True
+
+            index += step
+
+        return True
+
+    def is_simple_operand(index: int, kind: Literal["base", "exponent"]) -> bool:
+        # An operand is considered "simple" if's a NAME, a numeric CONSTANT, a simple
+        # lookup (see above), with or without a preceding unary operator.
+        start = line.leaves[index]
+        if start.type in {token.NAME, token.NUMBER}:
+            return is_simple_lookup(index, step=(1 if kind == "exponent" else -1))
+
+        if start.type in {token.PLUS, token.MINUS, token.TILDE}:
+            if line.leaves[index + 1].type in {token.NAME, token.NUMBER}:
+                # step is always one as bases with a preceding unary op will be checked
+                # for simplicity starting from the next token (so it'll hit the check
+                # above).
+                return is_simple_lookup(index + 1, step=1)
+
+        return False
+
+    new_line = line.clone()
+    should_hug = False
+    for idx, leaf in enumerate(line.leaves):
+        new_leaf = leaf.clone()
+        if should_hug:
+            new_leaf.prefix = ""
+            should_hug = False
+
+        should_hug = (
+            (0 < idx < len(line.leaves) - 1)
+            and leaf.type == token.DOUBLESTAR
+            and is_simple_operand(idx - 1, kind="base")
+            and line.leaves[idx - 1].value != "lambda"
+            and is_simple_operand(idx + 1, kind="exponent")
+        )
+        if should_hug:
+            new_leaf.prefix = ""
+
+        # We have to be careful to make a new line properly:
+        # - bracket related metadata must be maintained (handled by Line.append)
+        # - comments need to copied over, updating the leaf IDs they're attached to
+        new_line.append(new_leaf, preformatted=True)
+        for comment_leaf in line.comments_after(leaf):
+            new_line.append(comment_leaf, preformatted=True)
+
+    yield new_line
+
+
 class StringTransformer(ABC):
     """
     An implementation of the Transformer protocol that relies on its
@@ -89,31 +188,40 @@ class StringTransformer(ABC):
         as much as possible.
     """
 
-    line_length: int
-    normalize_strings: bool
-    __name__ = "StringTransformer"
+    __name__: Final = "StringTransformer"
+
+    # Ideally this would be a dataclass, but unfortunately mypyc breaks when used with
+    # `abc.ABC`.
+    def __init__(self, line_length: int, normalize_strings: bool) -> None:
+        self.line_length = line_length
+        self.normalize_strings = normalize_strings
 
     @abstractmethod
     def do_match(self, line: Line) -> TMatchResult:
         """
         Returns:
-            * Ok(string_idx) such that `line.leaves[string_idx]` is our target
-            string, if a match was able to be made.
-                OR
-            * Err(CannotTransform), if a match was not able to be made.
+            * Ok(string_indices) such that for each index, `line.leaves[index]`
+              is our target string if a match was able to be made. For
+              transformers that don't result in more lines (e.g. StringMerger,
+              StringParenStripper), multiple matches and transforms are done at
+              once to reduce the complexity.
+              OR
+            * Err(CannotTransform), if no match could be made.
         """
 
     @abstractmethod
-    def do_transform(self, line: Line, string_idx: int) -> Iterator[TResult[Line]]:
+    def do_transform(
+        self, line: Line, string_indices: List[int]
+    ) -> Iterator[TResult[Line]]:
         """
         Yields:
             * Ok(new_line) where new_line is the new transformed line.
-                OR
+              OR
             * Err(CannotTransform) if the transformation failed for some reason. The
-            `do_match(...)` template method should usually be used to reject
-            the form of the given Line, but in some cases it is difficult to
-            know whether or not a Line meets the StringTransformer's
-            requirements until the transformation is already midway.
+              `do_match(...)` template method should usually be used to reject
+              the form of the given Line, but in some cases it is difficult to
+              know whether or not a Line meets the StringTransformer's
+              requirements until the transformation is already midway.
 
         Side Effects:
             This method should NOT mutate @line directly, but it MAY mutate the
@@ -122,7 +230,9 @@ class StringTransformer(ABC):
             yield an CannotTransform after that point.)
         """
 
-    def __call__(self, line: Line, _features: Collection[Feature]) -> Iterator[Line]:
+    def __call__(
+        self, line: Line, _features: Collection[Feature], _mode: Mode
+    ) -> Iterator[Line]:
         """
         StringTransformer instances have a call signature that mirrors that of
         the Transformer type.
@@ -145,9 +255,9 @@ class StringTransformer(ABC):
                 " this line as one that it can transform."
             ) from cant_transform
 
-        string_idx = match_result.ok()
+        string_indices = match_result.ok()
 
-        for line_result in self.do_transform(line, string_idx):
+        for line_result in self.do_transform(line, string_indices):
             if isinstance(line_result, Err):
                 cant_transform = line_result.err()
                 raise CannotTransform(
@@ -183,6 +293,7 @@ class CustomSplit:
     break_idx: int
 
 
+@trait
 class CustomSplitMapMixin:
     """
     This mixin class is used to map merged strings to a sequence of
@@ -190,8 +301,10 @@ class CustomSplitMapMixin:
     the resultant substrings go over the configured max line length.
     """
 
-    _Key = Tuple[StringID, str]
-    _CUSTOM_SPLIT_MAP: Dict[_Key, Tuple[CustomSplit, ...]] = defaultdict(tuple)
+    _Key: ClassVar = Tuple[StringID, str]
+    _CUSTOM_SPLIT_MAP: ClassVar[Dict[_Key, Tuple[CustomSplit, ...]]] = defaultdict(
+        tuple
+    )
 
     @staticmethod
     def _get_key(string: str) -> "CustomSplitMapMixin._Key":
@@ -218,8 +331,8 @@ class CustomSplitMapMixin:
 
         Returns:
             * A list of the custom splits that are mapped to @string, if any
-            exist.
-                OR
+              exist.
+              OR
             * [], otherwise.
 
         Side Effects:
@@ -242,20 +355,20 @@ class CustomSplitMapMixin:
         return key in self._CUSTOM_SPLIT_MAP
 
 
-class StringMerger(CustomSplitMapMixin, StringTransformer):
+class StringMerger(StringTransformer, CustomSplitMapMixin):
     """StringTransformer that merges strings together.
 
     Requirements:
         (A) The line contains adjacent strings such that ALL of the validation checks
-        listed in StringMerger.__validate_msg(...)'s docstring pass.
-            OR
+        listed in StringMerger._validate_msg(...)'s docstring pass.
+        OR
         (B) The line contains a string which uses line continuation backslashes.
 
     Transformations:
         Depending on which of the two requirements above where met, either:
 
         (A) The string group associated with the target string is merged.
-            OR
+        OR
         (B) All line-continuation backslashes are removed from the target string.
 
     Collaborations:
@@ -267,28 +380,50 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
 
         is_valid_index = is_valid_index_factory(LL)
 
-        for (i, leaf) in enumerate(LL):
+        string_indices = []
+        idx = 0
+        while is_valid_index(idx):
+            leaf = LL[idx]
             if (
                 leaf.type == token.STRING
-                and is_valid_index(i + 1)
-                and LL[i + 1].type == token.STRING
+                and is_valid_index(idx + 1)
+                and LL[idx + 1].type == token.STRING
             ):
-                return Ok(i)
+                if not is_part_of_annotation(leaf):
+                    string_indices.append(idx)
+
+                # Advance to the next non-STRING leaf.
+                idx += 2
+                while is_valid_index(idx) and LL[idx].type == token.STRING:
+                    idx += 1
+
+            elif leaf.type == token.STRING and "\\\n" in leaf.value:
+                string_indices.append(idx)
+                # Advance to the next non-STRING leaf.
+                idx += 1
+                while is_valid_index(idx) and LL[idx].type == token.STRING:
+                    idx += 1
 
-            if leaf.type == token.STRING and "\\\n" in leaf.value:
-                return Ok(i)
+            else:
+                idx += 1
 
-        return TErr("This line has no strings that need merging.")
+        if string_indices:
+            return Ok(string_indices)
+        else:
+            return TErr("This line has no strings that need merging.")
 
-    def do_transform(self, line: Line, string_idx: int) -> Iterator[TResult[Line]]:
+    def do_transform(
+        self, line: Line, string_indices: List[int]
+    ) -> Iterator[TResult[Line]]:
         new_line = line
+
         rblc_result = self._remove_backslash_line_continuation_chars(
-            new_line, string_idx
+            new_line, string_indices
         )
         if isinstance(rblc_result, Ok):
             new_line = rblc_result.ok()
 
-        msg_result = self._merge_string_group(new_line, string_idx)
+        msg_result = self._merge_string_group(new_line, string_indices)
         if isinstance(msg_result, Ok):
             new_line = msg_result.ok()
 
@@ -309,7 +444,7 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
 
     @staticmethod
     def _remove_backslash_line_continuation_chars(
-        line: Line, string_idx: int
+        line: Line, string_indices: List[int]
     ) -> TResult[Line]:
         """
         Merge strings that were split across multiple lines using
@@ -323,34 +458,44 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
         """
         LL = line.leaves
 
-        string_leaf = LL[string_idx]
-        if not (
-            string_leaf.type == token.STRING
-            and "\\\n" in string_leaf.value
-            and not has_triple_quotes(string_leaf.value)
-        ):
+        indices_to_transform = []
+        for string_idx in string_indices:
+            string_leaf = LL[string_idx]
+            if (
+                string_leaf.type == token.STRING
+                and "\\\n" in string_leaf.value
+                and not has_triple_quotes(string_leaf.value)
+            ):
+                indices_to_transform.append(string_idx)
+
+        if not indices_to_transform:
             return TErr(
-                f"String leaf {string_leaf} does not contain any backslash line"
-                " continuation characters."
+                "Found no string leaves that contain backslash line continuation"
+                " characters."
             )
 
         new_line = line.clone()
         new_line.comments = line.comments.copy()
         append_leaves(new_line, line, LL)
 
-        new_string_leaf = new_line.leaves[string_idx]
-        new_string_leaf.value = new_string_leaf.value.replace("\\\n", "")
+        for string_idx in indices_to_transform:
+            new_string_leaf = new_line.leaves[string_idx]
+            new_string_leaf.value = new_string_leaf.value.replace("\\\n", "")
 
         return Ok(new_line)
 
-    def _merge_string_group(self, line: Line, string_idx: int) -> TResult[Line]:
+    def _merge_string_group(
+        self, line: Line, string_indices: List[int]
+    ) -> TResult[Line]:
         """
-        Merges string group (i.e. set of adjacent strings) where the first
-        string in the group is `line.leaves[string_idx]`.
+        Merges string groups (i.e. set of adjacent strings).
+
+        Each index from `string_indices` designates one string group's first
+        leaf in `line.leaves`.
 
         Returns:
             Ok(new_line), if ALL of the validation checks found in
-            __validate_msg(...) pass.
+            _validate_msg(...) pass.
                 OR
             Err(CannotTransform), otherwise.
         """
@@ -358,10 +503,54 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
 
         is_valid_index = is_valid_index_factory(LL)
 
-        vresult = self._validate_msg(line, string_idx)
-        if isinstance(vresult, Err):
-            return vresult
+        # A dict of {string_idx: tuple[num_of_strings, string_leaf]}.
+        merged_string_idx_dict: Dict[int, Tuple[int, Leaf]] = {}
+        for string_idx in string_indices:
+            vresult = self._validate_msg(line, string_idx)
+            if isinstance(vresult, Err):
+                continue
+            merged_string_idx_dict[string_idx] = self._merge_one_string_group(
+                LL, string_idx, is_valid_index
+            )
+
+        if not merged_string_idx_dict:
+            return TErr("No string group is merged")
+
+        # Build the final line ('new_line') that this method will later return.
+        new_line = line.clone()
+        previous_merged_string_idx = -1
+        previous_merged_num_of_strings = -1
+        for i, leaf in enumerate(LL):
+            if i in merged_string_idx_dict:
+                previous_merged_string_idx = i
+                previous_merged_num_of_strings, string_leaf = merged_string_idx_dict[i]
+                new_line.append(string_leaf)
+
+            if (
+                previous_merged_string_idx
+                <= i
+                < previous_merged_string_idx + previous_merged_num_of_strings
+            ):
+                for comment_leaf in line.comments_after(LL[i]):
+                    new_line.append(comment_leaf, preformatted=True)
+                continue
+
+            append_leaves(new_line, line, [leaf])
+
+        return Ok(new_line)
 
+    def _merge_one_string_group(
+        self, LL: List[Leaf], string_idx: int, is_valid_index: Callable[[int], bool]
+    ) -> Tuple[int, Leaf]:
+        """
+        Merges one string group where the first string in the group is
+        `LL[string_idx]`.
+
+        Returns:
+            A tuple of `(num_of_strings, leaf)` where `num_of_strings` is the
+            number of strings merged and `leaf` is the newly merged string
+            to be replaced in the new line.
+        """
         # If the string group is wrapped inside an Atom node, we must make sure
         # to later replace that Atom with our new (merged) string leaf.
         atom_node = LL[string_idx].parent
@@ -387,6 +576,12 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
                 characters have been escaped.
             """
             assert_is_leaf_string(string)
+            if "f" in string_prefix:
+                string = _toggle_fexpr_quotes(string, QUOTE)
+                # After quotes toggling, quotes in expressions won't be escaped
+                # because quotes can't be reused in f-strings. So we can simply
+                # let the escaping logic below run without knowing f-string
+                # expressions.
 
             RE_EVEN_BACKSLASHES = r"(?:(?<!\\)(?:\\\\)*)"
             naked_string = string[len(string_prefix) + 1 : -1]
@@ -411,7 +606,7 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
             and is_valid_index(next_str_idx)
             and LL[next_str_idx].type == token.STRING
         ):
-            prefix = get_string_prefix(LL[next_str_idx].value)
+            prefix = get_string_prefix(LL[next_str_idx].value).lower()
             next_str_idx += 1
 
         # The next loop merges the string group. The final string will be
@@ -431,13 +626,13 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
             num_of_strings += 1
 
             SS = LL[next_str_idx].value
-            next_prefix = get_string_prefix(SS)
+            next_prefix = get_string_prefix(SS).lower()
 
             # If this is an f-string group but this substring is not prefixed
             # with 'f'...
             if "f" in prefix and "f" not in next_prefix:
                 # Then we must escape any braces contained in this substring.
-                SS = re.subf(r"(\{|\})", "{1}{1}", SS)
+                SS = re.sub(r"(\{|\})", r"\1\1", SS)
 
             NSS = make_naked(SS, next_prefix)
 
@@ -449,6 +644,9 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
 
             next_str_idx += 1
 
+        # Take a note on the index of the non-STRING leaf.
+        non_string_idx = next_str_idx
+
         S_leaf = Leaf(token.STRING, S)
         if self.normalize_strings:
             S_leaf.value = normalize_string_quotes(S_leaf.value)
@@ -468,29 +666,27 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
         string_leaf = Leaf(token.STRING, S_leaf.value.replace(BREAK_MARK, ""))
 
         if atom_node is not None:
-            replace_child(atom_node, string_leaf)
-
-        # Build the final line ('new_line') that this method will later return.
-        new_line = line.clone()
-        for (i, leaf) in enumerate(LL):
-            if i == string_idx:
-                new_line.append(string_leaf)
-
-            if string_idx <= i < string_idx + num_of_strings:
-                for comment_leaf in line.comments_after(LL[i]):
-                    new_line.append(comment_leaf, preformatted=True)
-                continue
-
-            append_leaves(new_line, line, [leaf])
+            # If not all children of the atom node are merged (this can happen
+            # when there is a standalone comment in the middle) ...
+            if non_string_idx - string_idx < len(atom_node.children):
+                # We need to replace the old STRING leaves with the new string leaf.
+                first_child_idx = LL[string_idx].remove()
+                for idx in range(string_idx + 1, non_string_idx):
+                    LL[idx].remove()
+                if first_child_idx is not None:
+                    atom_node.insert_child(first_child_idx, string_leaf)
+            else:
+                # Else replace the atom node with the new string leaf.
+                replace_child(atom_node, string_leaf)
 
         self.add_custom_splits(string_leaf.value, custom_splits)
-        return Ok(new_line)
+        return num_of_strings, string_leaf
 
     @staticmethod
     def _validate_msg(line: Line, string_idx: int) -> TResult[None]:
         """Validate (M)erge (S)tring (G)roup
 
-        Transform-time string validation logic for __merge_string_group(...).
+        Transform-time string validation logic for _merge_string_group(...).
 
         Returns:
             * Ok(None), if ALL validation checks (listed below) pass.
@@ -504,6 +700,11 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
                 - The set of all string prefixes in the string group is of
                   length greater than one and is not equal to {"", "f"}.
                 - The string group consists of raw strings.
+                - The string group is stringified type annotations. We don't want to
+                  process stringified type annotations since pyright doesn't support
+                  them spanning multiple string values. (NOTE: mypy, pytype, pyre do
+                  support them, so we can change if pyright also gains support in the
+                  future. See https://github.com/microsoft/pyright/issues/4359.)
         """
         # We first check for "inner" stand-alone comments (i.e. stand-alone
         # comments that have a string leaf before them AND after them).
@@ -541,7 +742,7 @@ class StringMerger(CustomSplitMapMixin, StringTransformer):
                 return TErr("StringMerger does NOT merge multiline strings.")
 
             num_of_strings += 1
-            prefix = get_string_prefix(leaf.value)
+            prefix = get_string_prefix(leaf.value).lower()
             if "r" in prefix:
                 return TErr("StringMerger does NOT merge raw strings.")
 
@@ -576,7 +777,7 @@ class StringParenStripper(StringTransformer):
             - The target string is NOT the only argument to a function call.
             - The target string is NOT a "pointless" string.
             - If the target string contains a PERCENT, the brackets are not
-              preceeded or followed by an operator with higher precedence than
+              preceded or followed by an operator with higher precedence than
               PERCENT.
 
     Transformations:
@@ -593,7 +794,15 @@ class StringParenStripper(StringTransformer):
 
         is_valid_index = is_valid_index_factory(LL)
 
-        for (idx, leaf) in enumerate(LL):
+        string_indices = []
+
+        idx = -1
+        while True:
+            idx += 1
+            if idx >= len(LL):
+                break
+            leaf = LL[idx]
+
             # Should be a string...
             if leaf.type != token.STRING:
                 continue
@@ -675,45 +884,76 @@ class StringParenStripper(StringTransformer):
                 }:
                     continue
 
-                return Ok(string_idx)
+                string_indices.append(string_idx)
+                idx = string_idx
+                while idx < len(LL) - 1 and LL[idx + 1].type == token.STRING:
+                    idx += 1
 
+        if string_indices:
+            return Ok(string_indices)
         return TErr("This line has no strings wrapped in parens.")
 
-    def do_transform(self, line: Line, string_idx: int) -> Iterator[TResult[Line]]:
+    def do_transform(
+        self, line: Line, string_indices: List[int]
+    ) -> Iterator[TResult[Line]]:
         LL = line.leaves
 
-        string_parser = StringParser()
-        rpar_idx = string_parser.parse(LL, string_idx)
+        string_and_rpar_indices: List[int] = []
+        for string_idx in string_indices:
+            string_parser = StringParser()
+            rpar_idx = string_parser.parse(LL, string_idx)
+
+            should_transform = True
+            for leaf in (LL[string_idx - 1], LL[rpar_idx]):
+                if line.comments_after(leaf):
+                    # Should not strip parentheses which have comments attached
+                    # to them.
+                    should_transform = False
+                    break
+            if should_transform:
+                string_and_rpar_indices.extend((string_idx, rpar_idx))
 
-        for leaf in (LL[string_idx - 1], LL[rpar_idx]):
-            if line.comments_after(leaf):
-                yield TErr(
-                    "Will not strip parentheses which have comments attached to them."
-                )
-                return
+        if string_and_rpar_indices:
+            yield Ok(self._transform_to_new_line(line, string_and_rpar_indices))
+        else:
+            yield Err(
+                CannotTransform("All string groups have comments attached to them.")
+            )
+
+    def _transform_to_new_line(
+        self, line: Line, string_and_rpar_indices: List[int]
+    ) -> Line:
+        LL = line.leaves
 
         new_line = line.clone()
         new_line.comments = line.comments.copy()
-        try:
-            append_leaves(new_line, line, LL[: string_idx - 1])
-        except BracketMatchError:
-            # HACK: I believe there is currently a bug somewhere in
-            # right_hand_split() that is causing brackets to not be tracked
-            # properly by a shared BracketTracker.
-            append_leaves(new_line, line, LL[: string_idx - 1], preformatted=True)
-
-        string_leaf = Leaf(token.STRING, LL[string_idx].value)
-        LL[string_idx - 1].remove()
-        replace_child(LL[string_idx], string_leaf)
-        new_line.append(string_leaf)
-
-        append_leaves(
-            new_line, line, LL[string_idx + 1 : rpar_idx] + LL[rpar_idx + 1 :]
-        )
 
-        LL[rpar_idx].remove()
+        previous_idx = -1
+        # We need to sort the indices, since string_idx and its matching
+        # rpar_idx may not come in order, e.g. in
+        # `("outer" % ("inner".join(items)))`, the "inner" string's
+        # string_idx is smaller than "outer" string's rpar_idx.
+        for idx in sorted(string_and_rpar_indices):
+            leaf = LL[idx]
+            lpar_or_rpar_idx = idx - 1 if leaf.type == token.STRING else idx
+            append_leaves(new_line, line, LL[previous_idx + 1 : lpar_or_rpar_idx])
+            if leaf.type == token.STRING:
+                string_leaf = Leaf(token.STRING, LL[idx].value)
+                LL[lpar_or_rpar_idx].remove()  # Remove lpar.
+                replace_child(LL[idx], string_leaf)
+                new_line.append(string_leaf)
+                # replace comments
+                old_comments = new_line.comments.pop(id(LL[idx]), [])
+                new_line.comments.setdefault(id(string_leaf), []).extend(old_comments)
+            else:
+                LL[lpar_or_rpar_idx].remove()  # This is a rpar.
+
+            previous_idx = idx
+
+        # Append the leaves after the last idx:
+        append_leaves(new_line, line, LL[idx + 1 :])
 
-        yield Ok(new_line)
+        return new_line
 
 
 class BaseStringSplitter(StringTransformer):
@@ -724,20 +964,35 @@ class BaseStringSplitter(StringTransformer):
 
     Requirements:
         * The target string value is responsible for the line going over the
-        line length limit. It follows that after all of black's other line
-        split methods have been exhausted, this line (or one of the resulting
-        lines after all line splits are performed) would still be over the
-        line_length limit unless we split this string.
-            AND
+          line length limit. It follows that after all of black's other line
+          split methods have been exhausted, this line (or one of the resulting
+          lines after all line splits are performed) would still be over the
+          line_length limit unless we split this string.
+          AND
+
         * The target string is NOT a "pointless" string (i.e. a string that has
-        no parent or siblings).
-            AND
+          no parent or siblings).
+          AND
+
         * The target string is not followed by an inline comment that appears
-        to be a pragma.
-            AND
+          to be a pragma.
+          AND
+
         * The target string is not a multiline (i.e. triple-quote) string.
     """
 
+    STRING_OPERATORS: Final = [
+        token.EQEQUAL,
+        token.GREATER,
+        token.GREATEREQUAL,
+        token.LESS,
+        token.LESSEQUAL,
+        token.NOTEQUAL,
+        token.PERCENT,
+        token.PLUS,
+        token.STAR,
+    ]
+
     @abstractmethod
     def do_splitter_match(self, line: Line) -> TMatchResult:
         """
@@ -754,7 +1009,12 @@ class BaseStringSplitter(StringTransformer):
         if isinstance(match_result, Err):
             return match_result
 
-        string_idx = match_result.ok()
+        string_indices = match_result.ok()
+        assert len(string_indices) == 1, (
+            f"{self.__class__.__name__} should only find one match at a time, found"
+            f" {len(string_indices)}"
+        )
+        string_idx = string_indices[0]
         vresult = self._validate(line, string_idx)
         if isinstance(vresult, Err):
             return vresult
@@ -769,7 +1029,7 @@ class BaseStringSplitter(StringTransformer):
 
         Returns:
             * Ok(None), if ALL of the requirements are met.
-                OR
+              OR
             * Err(CannotTransform), if ANY of the requirements are NOT met.
         """
         LL = line.leaves
@@ -847,15 +1107,15 @@ class BaseStringSplitter(StringTransformer):
                 p_idx -= 1
 
             P = LL[p_idx]
-            if P.type == token.PLUS:
-                # WMA4 a space and a '+' character (e.g. `+ STRING`).
-                offset += 2
+            if P.type in self.STRING_OPERATORS:
+                # WMA4 a space and a string operator (e.g. `+ STRING` or `== STRING`).
+                offset += len(str(P)) + 1
 
             if P.type == token.COMMA:
                 # WMA4 a space, a comma, and a closing bracket [e.g. `), STRING`].
                 offset += 3
 
-            if P.type in [token.COLON, token.EQUAL, token.NAME]:
+            if P.type in [token.COLON, token.EQUAL, token.PLUSEQUAL, token.NAME]:
                 # This conditional branch is meant to handle dictionary keys,
                 # variable assignments, 'return STRING' statement lines, and
                 # 'else STRING' ternary expression lines.
@@ -910,20 +1170,140 @@ class BaseStringSplitter(StringTransformer):
             # WMA4 the length of the inline comment.
             offset += len(comment_leaf.value)
 
-        max_string_length = self.line_length - offset
+        max_string_length = count_chars_in_width(str(line), self.line_length - offset)
         return max_string_length
 
+    @staticmethod
+    def _prefer_paren_wrap_match(LL: List[Leaf]) -> Optional[int]:
+        """
+        Returns:
+            string_idx such that @LL[string_idx] is equal to our target (i.e.
+            matched) string, if this line matches the "prefer paren wrap" statement
+            requirements listed in the 'Requirements' section of the StringParenWrapper
+            class's docstring.
+                OR
+            None, otherwise.
+        """
+        # The line must start with a string.
+        if LL[0].type != token.STRING:
+            return None
+
+        matching_nodes = [
+            syms.listmaker,
+            syms.dictsetmaker,
+            syms.testlist_gexp,
+        ]
+        # If the string is an immediate child of a list/set/tuple literal...
+        if (
+            parent_type(LL[0]) in matching_nodes
+            or parent_type(LL[0].parent) in matching_nodes
+        ):
+            # And the string is surrounded by commas (or is the first/last child)...
+            prev_sibling = LL[0].prev_sibling
+            next_sibling = LL[0].next_sibling
+            if (
+                not prev_sibling
+                and not next_sibling
+                and parent_type(LL[0]) == syms.atom
+            ):
+                # If it's an atom string, we need to check the parent atom's siblings.
+                parent = LL[0].parent
+                assert parent is not None  # For type checkers.
+                prev_sibling = parent.prev_sibling
+                next_sibling = parent.next_sibling
+            if (not prev_sibling or prev_sibling.type == token.COMMA) and (
+                not next_sibling or next_sibling.type == token.COMMA
+            ):
+                return 0
+
+        return None
+
+
+def iter_fexpr_spans(s: str) -> Iterator[Tuple[int, int]]:
+    """
+    Yields spans corresponding to expressions in a given f-string.
+    Spans are half-open ranges (left inclusive, right exclusive).
+    Assumes the input string is a valid f-string, but will not crash if the input
+    string is invalid.
+    """
+    stack: List[int] = []  # our curly paren stack
+    i = 0
+    while i < len(s):
+        if s[i] == "{":
+            # if we're in a string part of the f-string, ignore escaped curly braces
+            if not stack and i + 1 < len(s) and s[i + 1] == "{":
+                i += 2
+                continue
+            stack.append(i)
+            i += 1
+            continue
+
+        if s[i] == "}":
+            if not stack:
+                i += 1
+                continue
+            j = stack.pop()
+            # we've made it back out of the expression! yield the span
+            if not stack:
+                yield (j, i + 1)
+            i += 1
+            continue
+
+        # if we're in an expression part of the f-string, fast forward through strings
+        # note that backslashes are not legal in the expression portion of f-strings
+        if stack:
+            delim = None
+            if s[i : i + 3] in ("'''", '"""'):
+                delim = s[i : i + 3]
+            elif s[i] in ("'", '"'):
+                delim = s[i]
+            if delim:
+                i += len(delim)
+                while i < len(s) and s[i : i + len(delim)] != delim:
+                    i += 1
+                i += len(delim)
+                continue
+        i += 1
+
+
+def fstring_contains_expr(s: str) -> bool:
+    return any(iter_fexpr_spans(s))
+
+
+def _toggle_fexpr_quotes(fstring: str, old_quote: str) -> str:
+    """
+    Toggles quotes used in f-string expressions that are `old_quote`.
+
+    f-string expressions can't contain backslashes, so we need to toggle the
+    quotes if the f-string itself will end up using the same quote. We can
+    simply toggle without escaping because, quotes can't be reused in f-string
+    expressions. They will fail to parse.
 
-class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
+    NOTE: If PEP 701 is accepted, above statement will no longer be true.
+    Though if quotes can be reused, we can simply reuse them without updates or
+    escaping, once Black figures out how to parse the new grammar.
+    """
+    new_quote = "'" if old_quote == '"' else '"'
+    parts = []
+    previous_index = 0
+    for start, end in iter_fexpr_spans(fstring):
+        parts.append(fstring[previous_index:start])
+        parts.append(fstring[start:end].replace(old_quote, new_quote))
+        previous_index = end
+    parts.append(fstring[previous_index:])
+    return "".join(parts)
+
+
+class StringSplitter(BaseStringSplitter, CustomSplitMapMixin):
     """
     StringTransformer that splits "atom" strings (i.e. strings which exist on
     lines by themselves).
 
     Requirements:
-        * The line consists ONLY of a single string (with the exception of a
-        '+' symbol which MAY exist at the start of the line), MAYBE a string
-        trailer, and MAYBE a trailing comma.
-            AND
+        * The line consists ONLY of a single string (possibly prefixed by a
+          string operator [e.g. '+' or '==']), MAYBE a string trailer, and MAYBE
+          a trailing comma.
+          AND
         * All of the requirements listed in BaseStringSplitter's docstring.
 
     Transformations:
@@ -952,28 +1332,32 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
         CustomSplit objects and add them to the custom split map.
     """
 
-    MIN_SUBSTR_SIZE = 6
-    # Matches an "f-expression" (e.g. {var}) that might be found in an f-string.
-    RE_FEXPR = r"""
-    (?<!\{) (?:\{\{)* \{ (?!\{)
-        (?:
-            [^\{\}]
-            | \{\{
-            | \}\}
-            | (?R)
-        )+?
-    (?<!\}) \} (?:\}\})* (?!\})
-    """
+    MIN_SUBSTR_SIZE: Final = 6
 
     def do_splitter_match(self, line: Line) -> TMatchResult:
         LL = line.leaves
 
+        if self._prefer_paren_wrap_match(LL) is not None:
+            return TErr("Line needs to be wrapped in parens first.")
+
         is_valid_index = is_valid_index_factory(LL)
 
         idx = 0
 
-        # The first leaf MAY be a '+' symbol...
-        if is_valid_index(idx) and LL[idx].type == token.PLUS:
+        # The first two leaves MAY be the 'not in' keywords...
+        if (
+            is_valid_index(idx)
+            and is_valid_index(idx + 1)
+            and [LL[idx].type, LL[idx + 1].type] == [token.NAME, token.NAME]
+            and str(LL[idx]) + str(LL[idx + 1]) == "not in"
+        ):
+            idx += 2
+        # Else the first leaf MAY be a string operator symbol or the 'in' keyword...
+        elif is_valid_index(idx) and (
+            LL[idx].type in self.STRING_OPERATORS
+            or LL[idx].type == token.NAME
+            and str(LL[idx]) == "in"
+        ):
             idx += 1
 
         # The next/first leaf MAY be an empty LPAR...
@@ -1002,69 +1386,81 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
         if is_valid_index(idx):
             return TErr("This line does not end with a string.")
 
-        return Ok(string_idx)
+        return Ok([string_idx])
 
-    def do_transform(self, line: Line, string_idx: int) -> Iterator[TResult[Line]]:
+    def do_transform(
+        self, line: Line, string_indices: List[int]
+    ) -> Iterator[TResult[Line]]:
         LL = line.leaves
+        assert len(string_indices) == 1, (
+            f"{self.__class__.__name__} should only find one match at a time, found"
+            f" {len(string_indices)}"
+        )
+        string_idx = string_indices[0]
 
         QUOTE = LL[string_idx].value[-1]
 
         is_valid_index = is_valid_index_factory(LL)
         insert_str_child = insert_str_child_factory(LL[string_idx])
 
-        prefix = get_string_prefix(LL[string_idx].value)
+        prefix = get_string_prefix(LL[string_idx].value).lower()
 
         # We MAY choose to drop the 'f' prefix from substrings that don't
         # contain any f-expressions, but ONLY if the original f-string
         # contains at least one f-expression. Otherwise, we will alter the AST
         # of the program.
-        drop_pointless_f_prefix = ("f" in prefix) and re.search(
-            self.RE_FEXPR, LL[string_idx].value, re.VERBOSE
+        drop_pointless_f_prefix = ("f" in prefix) and fstring_contains_expr(
+            LL[string_idx].value
         )
 
         first_string_line = True
-        starts_with_plus = LL[0].type == token.PLUS
 
-        def line_needs_plus() -> bool:
-            return first_string_line and starts_with_plus
+        string_op_leaves = self._get_string_operator_leaves(LL)
+        string_op_leaves_length = (
+            sum(len(str(prefix_leaf)) for prefix_leaf in string_op_leaves) + 1
+            if string_op_leaves
+            else 0
+        )
 
-        def maybe_append_plus(new_line: Line) -> None:
+        def maybe_append_string_operators(new_line: Line) -> None:
             """
             Side Effects:
-                If @line starts with a plus and this is the first line we are
-                constructing, this function appends a PLUS leaf to @new_line
-                and replaces the old PLUS leaf in the node structure. Otherwise
-                this function does nothing.
+                If @line starts with a string operator and this is the first
+                line we are constructing, this function appends the string
+                operator to @new_line and replaces the old string operator leaf
+                in the node structure. Otherwise this function does nothing.
             """
-            if line_needs_plus():
-                plus_leaf = Leaf(token.PLUS, "+")
-                replace_child(LL[0], plus_leaf)
-                new_line.append(plus_leaf)
+            maybe_prefix_leaves = string_op_leaves if first_string_line else []
+            for i, prefix_leaf in enumerate(maybe_prefix_leaves):
+                replace_child(LL[i], prefix_leaf)
+                new_line.append(prefix_leaf)
 
         ends_with_comma = (
             is_valid_index(string_idx + 1) and LL[string_idx + 1].type == token.COMMA
         )
 
-        def max_last_string() -> int:
+        def max_last_string_column() -> int:
             """
             Returns:
-                The max allowed length of the string value used for the last
-                line we will construct.
+                The max allowed width of the string value used for the last
+                line we will construct.  Note that this value means the width
+                rather than the number of characters (e.g., many East Asian
+                characters expand to two columns).
             """
             result = self.line_length
             result -= line.depth * 4
             result -= 1 if ends_with_comma else 0
-            result -= 2 if line_needs_plus() else 0
+            result -= string_op_leaves_length
             return result
 
-        # --- Calculate Max Break Index (for string value)
+        # --- Calculate Max Break Width (for string value)
         # We start with the line length limit
-        max_break_idx = self.line_length
+        max_break_width = self.line_length
         # The last index of a string of length N is N-1.
-        max_break_idx -= 1
+        max_break_width -= 1
         # Leading whitespace is not present in the string value (e.g. Leaf.value).
-        max_break_idx -= line.depth * 4
-        if max_break_idx < 0:
+        max_break_width -= line.depth * 4
+        if max_break_width < 0:
             yield TErr(
                 f"Unable to split {LL[string_idx].value} at such high of a line depth:"
                 f" {line.depth}"
@@ -1077,7 +1473,7 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
         # line limit.
         use_custom_breakpoints = bool(
             custom_splits
-            and all(csplit.break_idx <= max_break_idx for csplit in custom_splits)
+            and all(csplit.break_idx <= max_break_width for csplit in custom_splits)
         )
 
         # Temporary storage for the remaining chunk of the string line that
@@ -1093,7 +1489,7 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
             if use_custom_breakpoints:
                 return len(custom_splits) > 1
             else:
-                return len(rest_value) > max_last_string()
+                return str_width(rest_value) > max_last_string_column()
 
         string_line_results: List[Ok[Line]] = []
         while more_splits_should_be_made():
@@ -1103,7 +1499,10 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
                 break_idx = csplit.break_idx
             else:
                 # Algorithmic Split (automatic)
-                max_bidx = max_break_idx - 2 if line_needs_plus() else max_break_idx
+                max_bidx = (
+                    count_chars_in_width(rest_value, max_break_width)
+                    - string_op_leaves_length
+                )
                 maybe_break_idx = self._get_break_idx(rest_value, max_bidx)
                 if maybe_break_idx is None:
                     # If we are unable to algorithmically determine a good split
@@ -1124,21 +1523,37 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
 
             # --- Construct `next_value`
             next_value = rest_value[:break_idx] + QUOTE
+
+            # HACK: The following 'if' statement is a hack to fix the custom
+            # breakpoint index in the case of either: (a) substrings that were
+            # f-strings but will have the 'f' prefix removed OR (b) substrings
+            # that were not f-strings but will now become f-strings because of
+            # redundant use of the 'f' prefix (i.e. none of the substrings
+            # contain f-expressions but one or more of them had the 'f' prefix
+            # anyway; in which case, we will prepend 'f' to _all_ substrings).
+            #
+            # There is probably a better way to accomplish what is being done
+            # here...
+            #
+            # If this substring is an f-string, we _could_ remove the 'f'
+            # prefix, and the current custom split did NOT originally use a
+            # prefix...
             if (
-                # Are we allowed to try to drop a pointless 'f' prefix?
-                drop_pointless_f_prefix
-                # If we are, will we be successful?
-                and next_value != self._normalize_f_string(next_value, prefix)
+                use_custom_breakpoints
+                and not csplit.has_prefix
+                and (
+                    # `next_value == prefix + QUOTE` happens when the custom
+                    # split is an empty string.
+                    next_value == prefix + QUOTE
+                    or next_value != self._normalize_f_string(next_value, prefix)
+                )
             ):
-                # If the current custom split did NOT originally use a prefix,
-                # then `csplit.break_idx` will be off by one after removing
+                # Then `csplit.break_idx` will be off by one after removing
                 # the 'f' prefix.
-                break_idx = (
-                    break_idx + 1
-                    if use_custom_breakpoints and not csplit.has_prefix
-                    else break_idx
-                )
+                break_idx += 1
                 next_value = rest_value[:break_idx] + QUOTE
+
+            if drop_pointless_f_prefix:
                 next_value = self._normalize_f_string(next_value, prefix)
 
             # --- Construct `next_leaf`
@@ -1148,7 +1563,7 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
 
             # --- Construct `next_line`
             next_line = line.clone()
-            maybe_append_plus(next_line)
+            maybe_append_string_operators(next_line)
             next_line.append(next_leaf)
             string_line_results.append(Ok(next_line))
 
@@ -1169,7 +1584,7 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
         self._maybe_normalize_string_quotes(rest_leaf)
 
         last_line = line.clone()
-        maybe_append_plus(last_line)
+        maybe_append_string_operators(last_line)
 
         # If there are any leaves to the right of the target string...
         if is_valid_index(string_idx + 1):
@@ -1184,7 +1599,7 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
 
             # Try to fit them all on the same line with the last substring...
             if (
-                len(temp_value) <= max_last_string()
+                str_width(temp_value) <= max_last_string_column()
                 or LL[string_idx + 1].type == token.COMMA
             ):
                 last_line.append(rest_leaf)
@@ -1205,6 +1620,59 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
             last_line.comments = line.comments.copy()
             yield Ok(last_line)
 
+    def _iter_nameescape_slices(self, string: str) -> Iterator[Tuple[Index, Index]]:
+        """
+        Yields:
+            All ranges of @string which, if @string were to be split there,
+            would result in the splitting of an \\N{...} expression (which is NOT
+            allowed).
+        """
+        # True - the previous backslash was unescaped
+        # False - the previous backslash was escaped *or* there was no backslash
+        previous_was_unescaped_backslash = False
+        it = iter(enumerate(string))
+        for idx, c in it:
+            if c == "\\":
+                previous_was_unescaped_backslash = not previous_was_unescaped_backslash
+                continue
+            if not previous_was_unescaped_backslash or c != "N":
+                previous_was_unescaped_backslash = False
+                continue
+            previous_was_unescaped_backslash = False
+
+            begin = idx - 1  # the position of backslash before \N{...}
+            for idx, c in it:
+                if c == "}":
+                    end = idx
+                    break
+            else:
+                # malformed nameescape expression?
+                # should have been detected by AST parsing earlier...
+                raise RuntimeError(f"{self.__class__.__name__} LOGIC ERROR!")
+            yield begin, end
+
+    def _iter_fexpr_slices(self, string: str) -> Iterator[Tuple[Index, Index]]:
+        """
+        Yields:
+            All ranges of @string which, if @string were to be split there,
+            would result in the splitting of an f-expression (which is NOT
+            allowed).
+        """
+        if "f" not in get_string_prefix(string).lower():
+            return
+        yield from iter_fexpr_spans(string)
+
+    def _get_illegal_split_indices(self, string: str) -> Set[Index]:
+        illegal_indices: Set[Index] = set()
+        iterators = [
+            self._iter_fexpr_slices(string),
+            self._iter_nameescape_slices(string),
+        ]
+        for it in iterators:
+            for begin, end in it:
+                illegal_indices.update(range(begin, end + 1))
+        return illegal_indices
+
     def _get_break_idx(self, string: str, max_break_idx: int) -> Optional[int]:
         """
         This method contains the algorithm that StringSplitter uses to
@@ -1234,40 +1702,15 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
         assert is_valid_index(max_break_idx)
         assert_is_leaf_string(string)
 
-        _fexpr_slices: Optional[List[Tuple[Index, Index]]] = None
-
-        def fexpr_slices() -> Iterator[Tuple[Index, Index]]:
-            """
-            Yields:
-                All ranges of @string which, if @string were to be split there,
-                would result in the splitting of an f-expression (which is NOT
-                allowed).
-            """
-            nonlocal _fexpr_slices
-
-            if _fexpr_slices is None:
-                _fexpr_slices = []
-                for match in re.finditer(self.RE_FEXPR, string, re.VERBOSE):
-                    _fexpr_slices.append(match.span())
+        _illegal_split_indices = self._get_illegal_split_indices(string)
 
-            yield from _fexpr_slices
-
-        is_fstring = "f" in get_string_prefix(string)
-
-        def breaks_fstring_expression(i: Index) -> bool:
+        def breaks_unsplittable_expression(i: Index) -> bool:
             """
             Returns:
                 True iff returning @i would result in the splitting of an
-                f-expression (which is NOT allowed).
+                unsplittable expression (which is NOT allowed).
             """
-            if not is_fstring:
-                return False
-
-            for (start, end) in fexpr_slices():
-                if start <= i < end:
-                    return True
-
-            return False
+            return i in _illegal_split_indices
 
         def passes_all_checks(i: Index) -> bool:
             """
@@ -1276,6 +1719,7 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
                 section of this classes' docstring would be be met by returning @i.
             """
             is_space = string[i] == " "
+            is_split_safe = is_valid_index(i - 1) and string[i - 1] in SPLIT_SAFE_CHARS
 
             is_not_escaped = True
             j = i - 1
@@ -1288,10 +1732,10 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
                 and len(string[:i]) >= self.MIN_SUBSTR_SIZE
             )
             return (
-                is_space
+                (is_space or is_split_safe)
                 and is_not_escaped
                 and is_big_enough
-                and not breaks_fstring_expression(i)
+                and not breaks_unsplittable_expression(i)
             )
 
         # First, we check all indices BELOW @max_break_idx.
@@ -1333,7 +1777,7 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
         """
         assert_is_leaf_string(string)
 
-        if "f" in prefix and not re.search(self.RE_FEXPR, string, re.VERBOSE):
+        if "f" in prefix and not fstring_contains_expr(string):
             new_prefix = prefix.replace("f", "")
 
             temp = string[len(prefix) :]
@@ -1345,30 +1789,47 @@ class StringSplitter(CustomSplitMapMixin, BaseStringSplitter):
         else:
             return string
 
+    def _get_string_operator_leaves(self, leaves: Iterable[Leaf]) -> List[Leaf]:
+        LL = list(leaves)
+
+        string_op_leaves = []
+        i = 0
+        while LL[i].type in self.STRING_OPERATORS + [token.NAME]:
+            prefix_leaf = Leaf(LL[i].type, str(LL[i]).strip())
+            string_op_leaves.append(prefix_leaf)
+            i += 1
+        return string_op_leaves
 
-class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
+
+class StringParenWrapper(BaseStringSplitter, CustomSplitMapMixin):
     """
-    StringTransformer that splits non-"atom" strings (i.e. strings that do not
-    exist on lines by themselves).
+    StringTransformer that wraps strings in parens and then splits at the LPAR.
 
     Requirements:
         All of the requirements listed in BaseStringSplitter's docstring in
         addition to the requirements listed below:
 
         * The line is a return/yield statement, which returns/yields a string.
-            OR
+          OR
         * The line is part of a ternary expression (e.g. `x = y if cond else
-        z`) such that the line starts with `else <string>`, where <string> is
-        some string.
-            OR
+          z`) such that the line starts with `else <string>`, where <string> is
+          some string.
+          OR
         * The line is an assert statement, which ends with a string.
-            OR
+          OR
         * The line is an assignment statement (e.g. `x = <string>` or `x +=
-        <string>`) such that the variable is being assigned the value of some
-        string.
-            OR
+          <string>`) such that the variable is being assigned the value of some
+          string.
+          OR
         * The line is a dictionary key assignment where some valid key is being
-        assigned the value of some string.
+          assigned the value of some string.
+          OR
+        * The line is an lambda expression and the value is a string.
+          OR
+        * The line starts with an "atom" string that prefers to be wrapped in
+          parens. It's preferred to be wrapped when it's is an immediate child of
+          a list/set/tuple literal, AND the string is surrounded by commas (or is
+          the first/last child).
 
     Transformations:
         The chosen string is wrapped in parentheses and then split at the LPAR.
@@ -1393,26 +1854,37 @@ class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
         changed such that it no longer needs to be given its own line,
         StringParenWrapper relies on StringParenStripper to clean up the
         parentheses it created.
+
+        For "atom" strings that prefers to be wrapped in parens, it requires
+        StringSplitter to hold the split until the string is wrapped in parens.
     """
 
     def do_splitter_match(self, line: Line) -> TMatchResult:
         LL = line.leaves
 
+        if line.leaves[-1].type in OPENING_BRACKETS:
+            return TErr(
+                "Cannot wrap parens around a line that ends in an opening bracket."
+            )
+
         string_idx = (
             self._return_match(LL)
             or self._else_match(LL)
             or self._assert_match(LL)
             or self._assign_match(LL)
-            or self._dict_match(LL)
+            or self._dict_or_lambda_match(LL)
+            or self._prefer_paren_wrap_match(LL)
         )
 
         if string_idx is not None:
             string_value = line.leaves[string_idx].value
-            # If the string has no spaces...
-            if " " not in string_value:
+            # If the string has neither spaces nor East Asian stops...
+            if not any(
+                char == " " or char in SPLIT_SAFE_CHARS for char in string_value
+            ):
                 # And will still violate the line length limit when split...
-                max_string_length = self.line_length - ((line.depth + 1) * 4)
-                if len(string_value) > max_string_length:
+                max_string_width = self.line_length - ((line.depth + 1) * 4)
+                if str_width(string_value) > max_string_width:
                     # And has no associated custom splits...
                     if not self.has_custom_splits(string_value):
                         # Then we should NOT put this string on its own line.
@@ -1421,7 +1893,7 @@ class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
                             " resultant line would still be over the specified line"
                             " length and can't be split further by StringSplitter."
                         )
-            return Ok(string_idx)
+            return Ok([string_idx])
 
         return TErr("This line does not contain any non-atomic strings.")
 
@@ -1493,7 +1965,7 @@ class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
         if parent_type(LL[0]) == syms.assert_stmt and LL[0].value == "assert":
             is_valid_index = is_valid_index_factory(LL)
 
-            for (i, leaf) in enumerate(LL):
+            for i, leaf in enumerate(LL):
                 # We MUST find a comma...
                 if leaf.type == token.COMMA:
                     idx = i + 2 if is_empty_par(LL[i + 1]) else i + 1
@@ -1531,7 +2003,7 @@ class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
         ):
             is_valid_index = is_valid_index_factory(LL)
 
-            for (i, leaf) in enumerate(LL):
+            for i, leaf in enumerate(LL):
                 # We MUST find either an '=' or '+=' symbol...
                 if leaf.type in [token.EQUAL, token.PLUSEQUAL]:
                     idx = i + 2 if is_empty_par(LL[i + 1]) else i + 1
@@ -1560,23 +2032,24 @@ class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
         return None
 
     @staticmethod
-    def _dict_match(LL: List[Leaf]) -> Optional[int]:
+    def _dict_or_lambda_match(LL: List[Leaf]) -> Optional[int]:
         """
         Returns:
             string_idx such that @LL[string_idx] is equal to our target (i.e.
             matched) string, if this line matches the dictionary key assignment
-            statement requirements listed in the 'Requirements' section of this
-            classes' docstring.
+            statement or lambda expression requirements listed in the
+            'Requirements' section of this classes' docstring.
                 OR
             None, otherwise.
         """
-        # If this line is apart of a dictionary key assignment...
-        if syms.dictsetmaker in [parent_type(LL[0]), parent_type(LL[0].parent)]:
+        # If this line is a part of a dictionary key assignment or lambda expression...
+        parent_types = [parent_type(LL[0]), parent_type(LL[0].parent)]
+        if syms.dictsetmaker in parent_types or syms.lambdef in parent_types:
             is_valid_index = is_valid_index_factory(LL)
 
-            for (i, leaf) in enumerate(LL):
-                # We MUST find a colon...
-                if leaf.type == token.COLON:
+            for i, leaf in enumerate(LL):
+                # We MUST find a colon, it can either be dict's or lambda's colon...
+                if leaf.type == token.COLON and i < len(LL) - 1:
                     idx = i + 2 if is_empty_par(LL[i + 1]) else i + 1
 
                     # That colon MUST be followed by a string...
@@ -1597,8 +2070,15 @@ class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
 
         return None
 
-    def do_transform(self, line: Line, string_idx: int) -> Iterator[TResult[Line]]:
+    def do_transform(
+        self, line: Line, string_indices: List[int]
+    ) -> Iterator[TResult[Line]]:
         LL = line.leaves
+        assert len(string_indices) == 1, (
+            f"{self.__class__.__name__} should only find one match at a time, found"
+            f" {len(string_indices)}"
+        )
+        string_idx = string_indices[0]
 
         is_valid_index = is_valid_index_factory(LL)
         insert_str_child = insert_str_child_factory(LL[string_idx])
@@ -1665,10 +2145,30 @@ class StringParenWrapper(CustomSplitMapMixin, BaseStringSplitter):
                 right_leaves.pop()
 
             if old_parens_exist:
-                assert (
-                    right_leaves and right_leaves[-1].type == token.RPAR
-                ), "Apparently, old parentheses do NOT exist?!"
+                assert right_leaves and right_leaves[-1].type == token.RPAR, (
+                    "Apparently, old parentheses do NOT exist?!"
+                    f" (left_leaves={left_leaves}, right_leaves={right_leaves})"
+                )
                 old_rpar_leaf = right_leaves.pop()
+            elif right_leaves and right_leaves[-1].type == token.RPAR:
+                # Special case for lambda expressions as dict's value, e.g.:
+                #     my_dict = {
+                #        "key": lambda x: f"formatted: {x},
+                #     }
+                # After wrapping the dict's value with parentheses, the string is
+                # followed by a RPAR but its opening bracket is lambda's, not
+                # the string's:
+                #        "key": (lambda x: f"formatted: {x}),
+                opening_bracket = right_leaves[-1].opening_bracket
+                if opening_bracket is not None and opening_bracket in left_leaves:
+                    index = left_leaves.index(opening_bracket)
+                    if (
+                        index > 0
+                        and index < len(left_leaves) - 1
+                        and left_leaves[index - 1].type == token.COLON
+                        and left_leaves[index + 1].value == "lambda"
+                    ):
+                        right_leaves.pop()
 
             append_leaves(string_line, line, right_leaves)
 
@@ -1725,20 +2225,20 @@ class StringParser:
         ```
     """
 
-    DEFAULT_TOKEN = -1
+    DEFAULT_TOKEN: Final = 20210605
 
     # String Parser States
-    START = 1
-    DOT = 2
-    NAME = 3
-    PERCENT = 4
-    SINGLE_FMT_ARG = 5
-    LPAR = 6
-    RPAR = 7
-    DONE = 8
+    START: Final = 1
+    DOT: Final = 2
+    NAME: Final = 3
+    PERCENT: Final = 4
+    SINGLE_FMT_ARG: Final = 5
+    LPAR: Final = 6
+    RPAR: Final = 7
+    DONE: Final = 8
 
     # Lookup Table for Next State
-    _goto: Dict[Tuple[ParserState, NodeType], ParserState] = {
+    _goto: Final[Dict[Tuple[ParserState, NodeType], ParserState]] = {
         # A string trailer may start with '.' OR '%'.
         (START, token.DOT): DOT,
         (START, token.PERCENT): PERCENT,
@@ -1775,7 +2275,7 @@ class StringParser:
         Returns:
             The index directly after the last leaf which is apart of the string
             trailer, if a "trailer" exists.
-                OR
+            OR
             @string_idx + 1, if no string "trailer" exists.
         """
         assert leaves[string_idx].type == token.STRING
@@ -1789,11 +2289,11 @@ class StringParser:
         """
         Pre-conditions:
             * On the first call to this function, @leaf MUST be the leaf that
-            was directly after the string leaf in question (e.g. if our target
-            string is `line.leaves[i]` then the first call to this method must
-            be `line.leaves[i + 1]`).
+              was directly after the string leaf in question (e.g. if our target
+              string is `line.leaves[i]` then the first call to this method must
+              be `line.leaves[i + 1]`).
             * On the next call to this function, the leaf parameter passed in
-            MUST be the leaf directly following @leaf.
+              MUST be the leaf directly following @leaf.
 
         Returns:
             True iff @leaf is apart of the string's trailer.