+ assert len(line.leaves) >= 2, "Stranded delimiter"
+
+ first = line.leaves[0]
+ second = line.leaves[1]
+ penultimate = line.leaves[-2]
+ last = line.leaves[-1]
+
+ # With a single delimiter, omit if the expression starts or ends with
+ # a bracket.
+ if first.type in OPENING_BRACKETS and second.type not in CLOSING_BRACKETS:
+ remainder = False
+ length = 4 * line.depth
+ for _index, leaf, leaf_length in enumerate_with_length(line):
+ if leaf.type in CLOSING_BRACKETS and leaf.opening_bracket is first:
+ remainder = True
+ if remainder:
+ length += leaf_length
+ if length > line_length:
+ break
+
+ if leaf.type in OPENING_BRACKETS:
+ # There are brackets we can further split on.
+ remainder = False
+
+ else:
+ # checked the entire string and line length wasn't exceeded
+ if len(line.leaves) == _index + 1:
+ return True
+
+ # Note: we are not returning False here because a line might have *both*
+ # a leading opening bracket and a trailing closing bracket. If the
+ # opening bracket doesn't match our rule, maybe the closing will.
+
+ if (
+ last.type == token.RPAR
+ or last.type == token.RBRACE
+ or (
+ # don't use indexing for omitting optional parentheses;
+ # it looks weird
+ last.type == token.RSQB
+ and last.parent
+ and last.parent.type != syms.trailer
+ )
+ ):
+ if penultimate.type in OPENING_BRACKETS:
+ # Empty brackets don't help.
+ return False
+
+ if is_multiline_string(first):
+ # Additional wrapping of a multiline string in this situation is
+ # unnecessary.
+ return True
+
+ length = 4 * line.depth
+ seen_other_brackets = False
+ for _index, leaf, leaf_length in enumerate_with_length(line):
+ length += leaf_length
+ if leaf is last.opening_bracket:
+ if seen_other_brackets or length <= line_length:
+ return True