diff --git a/.github/workflows/lint.yml b/.github/workflows/lint.yml
index d1ad23bb2ab..9c7aca8f869 100644
--- a/.github/workflows/lint.yml
+++ b/.github/workflows/lint.yml
@@ -11,11 +11,7 @@ jobs:
       github.event_name == 'push' || github.event.pull_request.head.repo.full_name !=
       github.repository
 
-    runs-on: ${{ matrix.os }}
-    strategy:
-      fail-fast: false
-      matrix:
-        os: [ubuntu-latest, macOS-latest, windows-latest]
+    runs-on: ubuntu-latest
 
     steps:
       - uses: actions/checkout@v4
diff --git a/.github/workflows/pypi_upload.yml b/.github/workflows/pypi_upload.yml
index 07273f09508..bbdcdf17a8f 100644
--- a/.github/workflows/pypi_upload.yml
+++ b/.github/workflows/pypi_upload.yml
@@ -73,7 +73,7 @@ jobs:
             | pyp 'json.dumps({"only": x, "os": "ubuntu-latest"})'
           } | pyp 'json.dumps(list(map(json.loads, lines)))' > /tmp/matrix
         env:
-          CIBW_BUILD: "cp38-* cp311-*"
+          CIBW_BUILD: "cp38-* cp312-*"
           CIBW_ARCHS_LINUX: x86_64
       - id: set-matrix
         run: echo "include=$(cat /tmp/matrix)" | tee -a $GITHUB_OUTPUT
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index c153746b621..2896489d724 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -39,7 +39,7 @@ repos:
         exclude: ^src/blib2to3/
 
   - repo: https://github.com/pre-commit/mirrors-mypy
-    rev: v1.6.1
+    rev: v1.7.1
     hooks:
       - id: mypy
         exclude: ^docs/conf.py
diff --git a/CHANGES.md b/CHANGES.md
index 41a4f86c19a..fa0d2494f67 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -8,15 +8,18 @@
 
 ### Stable style
 
-<!-- Changes that affect Black's stable style -->
+- Fix bug where `# fmt: off` automatically dedents when used with the `--line-ranges`
+  option, even when it is not within the specified line range. (#4084)
 
 ### Preview style
 
+- Prefer more equal signs before a break when splitting chained assignments (#4010)
 - Standalone form feed characters at the module level are no longer removed (#4021)
 - Additional cases of immediately nested tuples, lists, and dictionaries are now
   indented less (#4012)
 - Allow empty lines at the beginning of all blocks, except immediately before a
   docstring (#4060)
+- Fix crash in preview mode when using a short `--line-length` (#4086)
 
 ### Configuration
 
@@ -27,7 +30,8 @@
 
 ### Packaging
 
-- Upgrade to mypy 1.6.1 (#4049)
+- Upgrade to mypy 1.7.1 (#4049) (#4069)
+- Faster compiled wheels are now available for CPython 3.12 (#4070)
 
 ### Parser
 
diff --git a/docs/the_black_code_style/current_style.md b/docs/the_black_code_style/current_style.md
index 2a5e10162f2..00bd81416dc 100644
--- a/docs/the_black_code_style/current_style.md
+++ b/docs/the_black_code_style/current_style.md
@@ -8,18 +8,9 @@ deliberately limited and rarely added. Previous formatting is taken into account
 little as possible, with rare exceptions like the magic trailing comma. The coding style
 used by _Black_ can be viewed as a strict subset of PEP 8.
 
-_Black_ reformats entire files in place. It doesn't reformat lines that contain
-`# fmt: skip` or blocks that start with `# fmt: off` and end with `# fmt: on`.
-`# fmt: skip` can be mixed with other pragmas/comments either with multiple comments
-(e.g. `# fmt: skip # pylint # noqa`) or as a semicolon separated list (e.g.
-`# fmt: skip; pylint; noqa`). `# fmt: on/off` must be on the same level of indentation
-and in the same block, meaning no unindents beyond the initial indentation level between
-them. It also recognizes [YAPF](https://github.com/google/yapf)'s block comments to the
-same effect, as a courtesy for straddling code.
-
-The rest of this document describes the current formatting style. If you're interested
-in trying out where the style is heading, see [future style](./future_style.md) and try
-running `black --preview`.
+This document describes the current formatting style. If you're interested in trying out
+where the style is heading, see [future style](./future_style.md) and try running
+`black --preview`.
 
 ### How _Black_ wraps lines
 
diff --git a/docs/usage_and_configuration/the_basics.md b/docs/usage_and_configuration/the_basics.md
index 0c1a4d3b5a1..eb92887f64f 100644
--- a/docs/usage_and_configuration/the_basics.md
+++ b/docs/usage_and_configuration/the_basics.md
@@ -12,7 +12,8 @@ _Black_ is a well-behaved Unix-style command-line tool:
 
 ## Usage
 
-To get started right away with sensible defaults:
+_Black_ will reformat entire files in place. To get started right away with sensible
+defaults:
 
 ```sh
 black {source_file_or_directory}
@@ -24,6 +25,17 @@ You can run _Black_ as a package if running it as a script doesn't work:
 python -m black {source_file_or_directory}
 ```
 
+### Ignoring sections
+
+Black will not reformat lines that contain `# fmt: skip` or blocks that start with
+`# fmt: off` and end with `# fmt: on`. `# fmt: skip` can be mixed with other
+pragmas/comments either with multiple comments (e.g. `# fmt: skip # pylint # noqa`) or
+as a semicolon separated list (e.g. `# fmt: skip; pylint; noqa`). `# fmt: on/off` must
+be on the same level of indentation and in the same block, meaning no unindents beyond
+the initial indentation level between them. Black also recognizes
+[YAPF](https://github.com/google/yapf)'s block comments to the same effect, as a
+courtesy for straddling code.
+
 ### Command line options
 
 The CLI options of _Black_ can be displayed by running `black --help`. All options are
@@ -35,6 +47,10 @@ are deliberately limited and rarely added.
 Note that all command-line options listed above can also be configured using a
 `pyproject.toml` file (more on that below).
 
+#### `-h`, `--help`
+
+Show available command-line options and exit.
+
 #### `-c`, `--code`
 
 Format the code passed in as a string.
@@ -109,6 +125,10 @@ useful when piping source on standard input.
 When processing Jupyter Notebooks, add the given magic to the list of known python-
 magics. Useful for formatting cells with custom python magics.
 
+#### `-x, --skip-source-first-line`
+
+Skip the first line of the source code.
+
 #### `-S, --skip-string-normalization`
 
 By default, _Black_ uses double quotes for all strings and normalizes string prefixes,
@@ -132,7 +152,7 @@ functionality in the next major release. Read more about
 
 #### `--check`
 
-Passing `--check` will make _Black_ exit with:
+Don't write the files back, just return the status. _Black_ will exit with:
 
 - code 0 if nothing would change;
 - code 1 if some files would be reformatted; or
@@ -162,8 +182,8 @@ $ echo $?
 
 #### `--diff`
 
-Passing `--diff` will make _Black_ print out diffs that indicate what changes _Black_
-would've made. They are printed to stdout so capturing them is simple.
+Don't write the files back, just output a diff to indicate what changes _Black_ would've
+made. They are printed to stdout so capturing them is simple.
 
 If you'd like colored diffs, you can enable them with `--color`.
 
@@ -179,7 +199,11 @@ All done! ✨ 🍰 ✨
 1 file would be reformatted.
 ```
 
-### `--line-ranges`
+#### `--color` / `--no-color`
+
+Show (or do not show) colored diff. Only applies when `--diff` is given.
+
+#### `--line-ranges`
 
 When specified, _Black_ will try its best to only format these lines.
 
@@ -202,10 +226,6 @@ extra lines outside of the ranges when ther are unformatted lines with the exact
 content. It also disables _Black_'s formatting stability check in `--safe` mode.
 ```
 
-#### `--color` / `--no-color`
-
-Show (or do not show) colored diff. Only applies when `--diff` is given.
-
 #### `--fast` / `--safe`
 
 By default, _Black_ performs [an AST safety check](labels/ast-changes) after formatting
@@ -241,29 +261,22 @@ Because of our [stability policy](../the_black_code_style/index.md), this will g
 stable formatting, but still allow you to take advantage of improvements that do not
 affect formatting.
 
-#### `--include`
-
-A regular expression that matches files and directories that should be included on
-recursive searches. An empty value means all files are included regardless of the name.
-Use forward slashes for directories on all platforms (Windows, too). Exclusions are
-calculated first, inclusions later.
-
 #### `--exclude`
 
 A regular expression that matches files and directories that should be excluded on
 recursive searches. An empty value means no paths are excluded. Use forward slashes for
-directories on all platforms (Windows, too). Exclusions are calculated first, inclusions
-later.
+directories on all platforms (Windows, too). By default, Black also ignores all paths
+listed in `.gitignore`. Changing this value will override all default exclusions.
 
 #### `--extend-exclude`
 
-Like `--exclude`, but adds additional files and directories on top of the excluded ones.
-Useful if you simply want to add to the default.
+Like `--exclude`, but adds additional files and directories on top of the default values
+instead of overriding them.
 
 #### `--force-exclude`
 
 Like `--exclude`, but files and directories matching this regex will be excluded even
-when they are passed explicitly as arguments. This is useful when invoking _Black_
+when they are passed explicitly as arguments. This is useful when invoking Black
 programmatically on changed files, such as in a pre-commit hook or editor plugin.
 
 #### `--stdin-filename`
@@ -271,16 +284,23 @@ programmatically on changed files, such as in a pre-commit hook or editor plugin
 The name of the file when passing it through stdin. Useful to make sure Black will
 respect the `--force-exclude` option on some editors that rely on using stdin.
 
+#### `--include`
+
+A regular expression that matches files and directories that should be included on
+recursive searches. An empty value means all files are included regardless of the name.
+Use forward slashes for directories on all platforms (Windows, too). Overrides all
+exclusions, including from `.gitignore` and command line options.
+
 #### `-W`, `--workers`
 
 When _Black_ formats multiple files, it may use a process pool to speed up formatting.
 This option controls the number of parallel workers. This can also be specified via the
-`BLACK_NUM_WORKERS` environment variable.
+`BLACK_NUM_WORKERS` environment variable. Defaults to the number of CPUs in the system.
 
 #### `-q`, `--quiet`
 
-Passing `-q` / `--quiet` will cause _Black_ to stop emitting all non-critical output.
-Error messages will still be emitted (which can silenced by `2>/dev/null`).
+Stop emitting all non-critical output. Error messages will still be emitted (which can
+silenced by `2>/dev/null`).
 
 ```console
 $ black src/ -q
@@ -289,9 +309,9 @@ error: cannot format src/black_primer/cli.py: Cannot parse: 5:6: mport asyncio
 
 #### `-v`, `--verbose`
 
-Passing `-v` / `--verbose` will cause _Black_ to also emit messages about files that
-were not changed or were ignored due to exclusion patterns. If _Black_ is using a
-configuration file, a blue message detailing which one it is using will be emitted.
+Emit messages about files that were not changed or were ignored due to exclusion
+patterns. If _Black_ is using a configuration file, a message detailing which one it is
+using will be emitted.
 
 ```console
 $ black src/ -v
@@ -321,10 +341,6 @@ black, 23.11.0
 Read configuration options from a configuration file. See
 [below](#configuration-via-a-file) for more details on the configuration file.
 
-#### `-h`, `--help`
-
-Show available command-line options and exit.
-
 ### Environment variable options
 
 _Black_ supports the following configuration via environment variables.
@@ -355,7 +371,7 @@ All done! ✨ 🍰 ✨
 use `--stdin-filename`. Useful to make sure _Black_ will respect the `--force-exclude`
 option on some editors that rely on using stdin.
 
-You can also pass code as a string using the `-c` / `--code` option.
+You can also pass code as a string using the `--code` option.
 
 ### Writeback and reporting
 
@@ -435,8 +451,7 @@ refers to the path to your home directory. On Windows, this will be something li
 You can also explicitly specify the path to a particular file that you want with
 `--config`. In this situation _Black_ will not look for any other file.
 
-If you're running with `--verbose`, you will see a blue message if a file was found and
-used.
+If you're running with `--verbose`, you will see a message if a file was found and used.
 
 Please note `blackd` will not use `pyproject.toml` configuration.
 
diff --git a/pyproject.toml b/pyproject.toml
index e63e0aea3ef..1098412981a 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -121,7 +121,7 @@ macos-max-compat = true
 enable-by-default = false
 dependencies = [
   "hatch-mypyc>=0.16.0",
-  "mypy==1.6.1",
+  "mypy==1.7.1",
   "click==8.1.3",  # avoid https://github.com/pallets/click/issues/2558
 ]
 require-runtime-dependencies = true
@@ -150,7 +150,7 @@ build-verbosity = 1
 # - Architecture (64-bit only): amd64 / x86_64, universal2, and arm64
 # - OS: Linux (no musl), Windows, and macOS
 build = "cp3*"
-skip = ["*-manylinux_i686", "*-musllinux_*", "*-win32", "pp*", "cp312-*"]
+skip = ["*-manylinux_i686", "*-musllinux_*", "*-win32", "pp*"]
 # This is the bare minimum needed to run the test suite. Pulling in the full
 # test_requirements.txt would download a bunch of other packages not necessary
 # here and would slow down the testing step a fair bit.
@@ -187,7 +187,7 @@ CC = "clang"
 build-frontend = { name = "build", args = ["--no-isolation"] }
 # Unfortunately, hatch doesn't respect MACOSX_DEPLOYMENT_TARGET
 before-build = [
-    "python -m pip install 'hatchling==1.18.0' hatch-vcs hatch-fancy-pypi-readme 'hatch-mypyc>=0.16.0' 'mypy==1.6.1' 'click==8.1.3'",
+    "python -m pip install 'hatchling==1.18.0' hatch-vcs hatch-fancy-pypi-readme 'hatch-mypyc>=0.16.0' 'mypy==1.7.1' 'click==8.1.3'",
     """sed -i '' -e "600,700s/'10_16'/os.environ['MACOSX_DEPLOYMENT_TARGET'].replace('.', '_')/" $(python -c 'import hatchling.builders.wheel as h; print(h.__file__)') """,
 ]
 
diff --git a/src/black/__init__.py b/src/black/__init__.py
index b33beeeeb23..5073fa748d5 100644
--- a/src/black/__init__.py
+++ b/src/black/__init__.py
@@ -235,25 +235,26 @@ def validate_regex(
     callback=target_version_option_callback,
     multiple=True,
     help=(
-        "Python versions that should be supported by Black's output. By default, Black"
-        " will try to infer this from the project metadata in pyproject.toml. If this"
-        " does not yield conclusive results, Black will use per-file auto-detection."
+        "Python versions that should be supported by Black's output. You should"
+        " include all versions that your code supports. By default, Black will infer"
+        " target versions from the project metadata in pyproject.toml. If this does"
+        " not yield conclusive results, Black will use per-file auto-detection."
     ),
 )
 @click.option(
     "--pyi",
     is_flag=True,
     help=(
-        "Format all input files like typing stubs regardless of file extension (useful"
-        " when piping source on standard input)."
+        "Format all input files like typing stubs regardless of file extension. This"
+        " is useful when piping source on standard input."
     ),
 )
 @click.option(
     "--ipynb",
     is_flag=True,
     help=(
-        "Format all input files like Jupyter Notebooks regardless of file extension "
-        "(useful when piping source on standard input)."
+        "Format all input files like Jupyter Notebooks regardless of file extension."
+        "This is useful when piping source on standard input."
     ),
 )
 @click.option(
@@ -310,14 +311,22 @@ def validate_regex(
 @click.option(
     "--diff",
     is_flag=True,
-    help="Don't write the files back, just output a diff for each file on stdout.",
+    help=(
+        "Don't write the files back, just output a diff to indicate what changes"
+        " Black would've made. They are printed to stdout so capturing them is simple."
+    ),
+)
+@click.option(
+    "--color/--no-color",
+    is_flag=True,
+    help="Show (or do not show) colored diff. Only applies when --diff is given.",
 )
 @click.option(
     "--line-ranges",
     multiple=True,
     metavar="START-END",
     help=(
-        "When specified, _Black_ will try its best to only format these lines. This"
+        "When specified, Black will try its best to only format these lines. This"
         " option can be specified multiple times, and a union of the lines will be"
         " formatted. Each range must be specified as two integers connected by a `-`:"
         " `<START>-<END>`. The `<START>` and `<END>` integer indices are 1-based and"
@@ -325,37 +334,25 @@ def validate_regex(
     ),
     default=(),
 )
-@click.option(
-    "--color/--no-color",
-    is_flag=True,
-    help="Show colored diff. Only applies when `--diff` is given.",
-)
 @click.option(
     "--fast/--safe",
     is_flag=True,
-    help="If --fast given, skip temporary sanity checks. [default: --safe]",
-)
-@click.option(
-    "--required-version",
-    type=str,
     help=(
-        "Require a specific version of Black to be running (useful for unifying results"
-        " across many environments e.g. with a pyproject.toml file). It can be"
-        " either a major version number or an exact version."
+        "By default, Black performs an AST safety check after formatting your code."
+        " The --fast flag turns off this check and the --safe flag explicitly enables"
+        " it. [default: --safe]"
     ),
 )
 @click.option(
-    "--include",
+    "--required-version",
     type=str,
-    default=DEFAULT_INCLUDES,
-    callback=validate_regex,
     help=(
-        "A regular expression that matches files and directories that should be"
-        " included on recursive searches. An empty value means all files are included"
-        " regardless of the name. Use forward slashes for directories on all platforms"
-        " (Windows, too). Exclusions are calculated first, inclusions later."
+        "Require a specific version of Black to be running. This is useful for"
+        " ensuring that all contributors to your project are using the same"
+        " version, because different versions of Black may format code a little"
+        " differently. This option can be set in a configuration file for consistent"
+        " results across environments."
     ),
-    show_default=True,
 )
 @click.option(
     "--exclude",
@@ -365,8 +362,8 @@ def validate_regex(
         "A regular expression that matches files and directories that should be"
         " excluded on recursive searches. An empty value means no paths are excluded."
         " Use forward slashes for directories on all platforms (Windows, too)."
-        " Exclusions are calculated first, inclusions later. [default:"
-        f" {DEFAULT_EXCLUDES}]"
+        " By default, Black also ignores all paths listed in .gitignore. Changing this"
+        f" value will override all default exclusions. [default: {DEFAULT_EXCLUDES}]"
     ),
     show_default=False,
 )
@@ -376,7 +373,7 @@ def validate_regex(
     callback=validate_regex,
     help=(
         "Like --exclude, but adds additional files and directories on top of the"
-        " excluded ones. (Useful if you simply want to add to the default)"
+        " default values instead of overriding them."
     ),
 )
 @click.option(
@@ -384,8 +381,10 @@ def validate_regex(
     type=str,
     callback=validate_regex,
     help=(
-        "Like --exclude, but files and directories matching this regex will be "
-        "excluded even when they are passed explicitly as arguments."
+        "Like --exclude, but files and directories matching this regex will be excluded"
+        " even when they are passed explicitly as arguments. This is useful when"
+        " invoking Black programmatically on changed files, such as in a pre-commit"
+        " hook or editor plugin."
     ),
 )
 @click.option(
@@ -393,19 +392,35 @@ def validate_regex(
     type=str,
     is_eager=True,
     help=(
-        "The name of the file when passing it through stdin. Useful to make "
-        "sure Black will respect --force-exclude option on some "
-        "editors that rely on using stdin."
+        "The name of the file when passing it through stdin. Useful to make sure Black"
+        " will respect the --force-exclude option on some editors that rely on using"
+        " stdin."
     ),
 )
+@click.option(
+    "--include",
+    type=str,
+    default=DEFAULT_INCLUDES,
+    callback=validate_regex,
+    help=(
+        "A regular expression that matches files and directories that should be"
+        " included on recursive searches. An empty value means all files are included"
+        " regardless of the name. Use forward slashes for directories on all platforms"
+        " (Windows, too). Overrides all exclusions, including from .gitignore and"
+        " command line options."
+    ),
+    show_default=True,
+)
 @click.option(
     "-W",
     "--workers",
     type=click.IntRange(min=1),
     default=None,
     help=(
-        "Number of parallel workers [default: BLACK_NUM_WORKERS environment variable "
-        "or number of CPUs in the system]"
+        "When Black formats multiple files, it may use a process pool to speed up"
+        " formatting. This option controls the number of parallel workers. This can"
+        " also be specified via the BLACK_NUM_WORKERS environment variable. Defaults"
+        " to the number of CPUs in the system."
     ),
 )
 @click.option(
@@ -413,8 +428,8 @@ def validate_regex(
     "--quiet",
     is_flag=True,
     help=(
-        "Don't emit non-error messages to stderr. Errors are still emitted; silence"
-        " those with 2>/dev/null."
+        "Stop emitting all non-critical output. Error messages will still be emitted"
+        " (which can silenced by 2>/dev/null)."
     ),
 )
 @click.option(
@@ -422,8 +437,9 @@ def validate_regex(
     "--verbose",
     is_flag=True,
     help=(
-        "Also emit messages to stderr about files that were not changed or were ignored"
-        " due to exclusion patterns."
+        "Emit messages about files that were not changed or were ignored due to"
+        " exclusion patterns. If Black is using a configuration file, a message"
+        " detailing which one it is using will be emitted."
     ),
 )
 @click.version_option(
@@ -454,7 +470,7 @@ def validate_regex(
     ),
     is_eager=True,
     callback=read_pyproject_toml,
-    help="Read configuration from FILE path.",
+    help="Read configuration options from a configuration file.",
 )
 @click.pass_context
 def main(  # noqa: C901
@@ -1180,7 +1196,7 @@ def _format_str_once(
         for feature in {Feature.PARENTHESIZED_CONTEXT_MANAGERS}
         if supports_feature(versions, feature)
     }
-    normalize_fmt_off(src_node, mode)
+    normalize_fmt_off(src_node, mode, lines)
     if lines:
         # This should be called after normalize_fmt_off.
         convert_unchanged_lines(src_node, lines)
diff --git a/src/black/comments.py b/src/black/comments.py
index 8a0e925fdc0..25413121199 100644
--- a/src/black/comments.py
+++ b/src/black/comments.py
@@ -1,7 +1,7 @@
 import re
 from dataclasses import dataclass
 from functools import lru_cache
-from typing import Final, Iterator, List, Optional, Union
+from typing import Collection, Final, Iterator, List, Optional, Tuple, Union
 
 from black.mode import Mode, Preview
 from black.nodes import (
@@ -161,14 +161,18 @@ def make_comment(content: str) -> str:
     return "#" + content
 
 
-def normalize_fmt_off(node: Node, mode: Mode) -> None:
+def normalize_fmt_off(
+    node: Node, mode: Mode, lines: Collection[Tuple[int, int]]
+) -> None:
     """Convert content between `# fmt: off`/`# fmt: on` into standalone comments."""
     try_again = True
     while try_again:
-        try_again = convert_one_fmt_off_pair(node, mode)
+        try_again = convert_one_fmt_off_pair(node, mode, lines)
 
 
-def convert_one_fmt_off_pair(node: Node, mode: Mode) -> bool:
+def convert_one_fmt_off_pair(
+    node: Node, mode: Mode, lines: Collection[Tuple[int, int]]
+) -> bool:
     """Convert content of a single `# fmt: off`/`# fmt: on` into a standalone comment.
 
     Returns True if a pair was converted.
@@ -213,7 +217,18 @@ def convert_one_fmt_off_pair(node: Node, mode: Mode) -> bool:
                     prefix[:previous_consumed] + "\n" * comment.newlines
                 )
             hidden_value = "".join(str(n) for n in ignored_nodes)
+            comment_lineno = leaf.lineno - comment.newlines
             if comment.value in FMT_OFF:
+                fmt_off_prefix = ""
+                if len(lines) > 0 and not any(
+                    comment_lineno >= line[0] and comment_lineno <= line[1]
+                    for line in lines
+                ):
+                    # keeping indentation of comment by preserving original whitespaces.
+                    fmt_off_prefix = prefix.split(comment.value)[0]
+                    if "\n" in fmt_off_prefix:
+                        fmt_off_prefix = fmt_off_prefix.split("\n")[-1]
+                standalone_comment_prefix += fmt_off_prefix
                 hidden_value = comment.value + "\n" + hidden_value
             if _contains_fmt_skip_comment(comment.value, mode):
                 hidden_value += "  " + comment.value
diff --git a/src/black/linegen.py b/src/black/linegen.py
index 7fbbe290d7e..073672a5ae7 100644
--- a/src/black/linegen.py
+++ b/src/black/linegen.py
@@ -744,7 +744,7 @@ def left_hand_split(
             if leaf.type in OPENING_BRACKETS:
                 matching_bracket = leaf
                 current_leaves = body_leaves
-    if not matching_bracket:
+    if not matching_bracket or not tail_leaves:
         raise CannotSplit("No brackets found")
 
     head = bracket_split_build_line(
@@ -910,24 +910,32 @@ def _maybe_split_omitting_optional_parens(
         try:
             # The RHSResult Omitting Optional Parens.
             rhs_oop = _first_right_hand_split(line, omit=omit)
-            if not (
+            prefer_splitting_rhs_mode = (
                 Preview.prefer_splitting_right_hand_side_of_assignments in line.mode
-                # the split is right after `=`
-                and len(rhs.head.leaves) >= 2
-                and rhs.head.leaves[-2].type == token.EQUAL
-                # the left side of assignment contains brackets
-                and any(leaf.type in BRACKETS for leaf in rhs.head.leaves[:-1])
-                # the left side of assignment is short enough (the -1 is for the ending
-                # optional paren)
-                and is_line_short_enough(
-                    rhs.head, mode=replace(mode, line_length=mode.line_length - 1)
+            )
+            is_split_right_after_equal = (
+                len(rhs.head.leaves) >= 2 and rhs.head.leaves[-2].type == token.EQUAL
+            )
+            rhs_head_contains_brackets = any(
+                leaf.type in BRACKETS for leaf in rhs.head.leaves[:-1]
+            )
+            # the -1 is for the ending optional paren
+            rhs_head_short_enough = is_line_short_enough(
+                rhs.head, mode=replace(mode, line_length=mode.line_length - 1)
+            )
+            rhs_head_explode_blocked_by_magic_trailing_comma = (
+                rhs.head.magic_trailing_comma is None
+            )
+            if (
+                not (
+                    prefer_splitting_rhs_mode
+                    and is_split_right_after_equal
+                    and rhs_head_contains_brackets
+                    and rhs_head_short_enough
+                    and rhs_head_explode_blocked_by_magic_trailing_comma
                 )
-                # the left side of assignment won't explode further because of magic
-                # trailing comma
-                and rhs.head.magic_trailing_comma is None
-                # the split by omitting optional parens isn't preferred by some other
-                # reason
-                and not _prefer_split_rhs_oop(rhs_oop, mode)
+                # the omit optional parens split is preferred by some other reason
+                or _prefer_split_rhs_oop_over_rhs(rhs_oop, rhs, mode)
             ):
                 yield from _maybe_split_omitting_optional_parens(
                     rhs_oop, line, mode, features=features, omit=omit
@@ -935,8 +943,12 @@ def _maybe_split_omitting_optional_parens(
                 return
 
         except CannotSplit as e:
-            if not (
-                can_be_split(rhs.body) or is_line_short_enough(rhs.body, mode=mode)
+            # For chained assignments we want to use the previous successful split
+            if line.is_chained_assignment:
+                pass
+
+            elif not can_be_split(rhs.body) and not is_line_short_enough(
+                rhs.body, mode=mode
             ):
                 raise CannotSplit(
                     "Splitting failed, body is still too long and can't be split."
@@ -960,10 +972,22 @@ def _maybe_split_omitting_optional_parens(
             yield result
 
 
-def _prefer_split_rhs_oop(rhs_oop: RHSResult, mode: Mode) -> bool:
+def _prefer_split_rhs_oop_over_rhs(
+    rhs_oop: RHSResult, rhs: RHSResult, mode: Mode
+) -> bool:
     """
-    Returns whether we should prefer the result from a split omitting optional parens.
+    Returns whether we should prefer the result from a split omitting optional parens
+    (rhs_oop) over the original (rhs).
     """
+    # If we have multiple targets, we prefer more `=`s on the head vs pushing them to
+    # the body
+    rhs_head_equal_count = [leaf.type for leaf in rhs.head.leaves].count(token.EQUAL)
+    rhs_oop_head_equal_count = [leaf.type for leaf in rhs_oop.head.leaves].count(
+        token.EQUAL
+    )
+    if rhs_head_equal_count > 1 and rhs_head_equal_count > rhs_oop_head_equal_count:
+        return False
+
     has_closing_bracket_after_assign = False
     for leaf in reversed(rhs_oop.head.leaves):
         if leaf.type == token.EQUAL:
diff --git a/src/black/lines.py b/src/black/lines.py
index 0f24192447d..4050f819757 100644
--- a/src/black/lines.py
+++ b/src/black/lines.py
@@ -209,6 +209,11 @@ def is_triple_quoted_string(self) -> bool:
             return True
         return False
 
+    @property
+    def is_chained_assignment(self) -> bool:
+        """Is the line a chained assignment"""
+        return [leaf.type for leaf in self.leaves].count(token.EQUAL) > 1
+
     @property
     def opens_block(self) -> bool:
         """Does this line open a new level of indentation."""
diff --git a/src/black/numerics.py b/src/black/numerics.py
index 67ac8595fcc..3040de06fde 100644
--- a/src/black/numerics.py
+++ b/src/black/numerics.py
@@ -14,7 +14,7 @@ def format_hex(text: str) -> str:
 
 
 def format_scientific_notation(text: str) -> str:
-    """Formats a numeric string utilizing scentific notation"""
+    """Formats a numeric string utilizing scientific notation"""
     before, after = text.split("e")
     sign = ""
     if after.startswith("-"):
diff --git a/src/black/ranges.py b/src/black/ranges.py
index b0c312e6274..59e19242d47 100644
--- a/src/black/ranges.py
+++ b/src/black/ranges.py
@@ -172,7 +172,7 @@ class _TopLevelStatementsVisitor(Visitor[None]):
     A node visitor that converts unchanged top-level statements to
     STANDALONE_COMMENT.
 
-    This is used in addition to _convert_unchanged_lines_by_flatterning, to
+    This is used in addition to _convert_unchanged_line_by_line, to
     speed up formatting when there are unchanged top-level
     classes/functions/statements.
     """
@@ -302,7 +302,7 @@ def _convert_node_to_standalone_comment(node: LN) -> None:
     index = node.remove()
     if index is not None:
         # Remove the '\n', as STANDALONE_COMMENT will have '\n' appended when
-        # genearting the formatted code.
+        # generating the formatted code.
         value = str(node)[:-1]
         parent.insert_child(
             index,
diff --git a/src/blib2to3/pgen2/tokenize.py b/src/blib2to3/pgen2/tokenize.py
index d0607f4b1e1..b04b18ba870 100644
--- a/src/blib2to3/pgen2/tokenize.py
+++ b/src/blib2to3/pgen2/tokenize.py
@@ -39,7 +39,6 @@
     Set,
     Tuple,
     Union,
-    cast,
 )
 
 from blib2to3.pgen2.grammar import Grammar
@@ -262,11 +261,9 @@ def add_whitespace(self, start: Coord) -> None:
     def untokenize(self, iterable: Iterable[TokenInfo]) -> str:
         for t in iterable:
             if len(t) == 2:
-                self.compat(cast(Tuple[int, str], t), iterable)
+                self.compat(t, iterable)
                 break
-            tok_type, token, start, end, line = cast(
-                Tuple[int, str, Coord, Coord, str], t
-            )
+            tok_type, token, start, end, line = t
             self.add_whitespace(start)
             self.tokens.append(token)
             self.prev_row, self.prev_col = end
diff --git a/tests/data/cases/comment_type_hint.py b/tests/data/cases/comment_type_hint.py
new file mode 100644
index 00000000000..2992da88d90
--- /dev/null
+++ b/tests/data/cases/comment_type_hint.py
@@ -0,0 +1,3 @@
+# flags: --no-preview-line-length-1
+# split out from comments2 as it does not work with line-length=1, losing the comment
+a = "type comment with trailing space"  # type: str
diff --git a/tests/data/cases/comments2.py b/tests/data/cases/comments2.py
index 1487dc4b6e2..261c5e9f0a0 100644
--- a/tests/data/cases/comments2.py
+++ b/tests/data/cases/comments2.py
@@ -155,8 +155,6 @@ def _init_host(self, parsed) -> None:
             pass
 
 
-a = "type comment with trailing space"  # type: str   
-
 #######################
 ### SECTION COMMENT ###
 #######################
@@ -335,8 +333,6 @@ def _init_host(self, parsed) -> None:
             pass
 
 
-a = "type comment with trailing space"  # type: str
-
 #######################
 ### SECTION COMMENT ###
 #######################
diff --git a/tests/data/cases/fmtskip2.py b/tests/data/cases/fmtskip2.py
index e6248117aa9..0189d4e642d 100644
--- a/tests/data/cases/fmtskip2.py
+++ b/tests/data/cases/fmtskip2.py
@@ -1,9 +1,12 @@
+# flags: --no-preview-line-length-1
+# l2 loses the comment with line-length=1 in preview mode
 l1 = ["This list should be broken up", "into multiple lines", "because it is way too long"]
 l2 = ["But this list shouldn't", "even though it also has", "way too many characters in it"]  # fmt: skip
 l3 = ["I have", "trailing comma", "so I should be braked",]
 
 # output
 
+# l2 loses the comment with line-length=1 in preview mode
 l1 = [
     "This list should be broken up",
     "into multiple lines",
@@ -14,4 +17,4 @@
     "I have",
     "trailing comma",
     "so I should be braked",
-]
\ No newline at end of file
+]
diff --git a/tests/data/cases/line_ranges_fmt_off_decorator.py b/tests/data/cases/line_ranges_fmt_off_decorator.py
index 14aa1dda02d..065bf4328d7 100644
--- a/tests/data/cases/line_ranges_fmt_off_decorator.py
+++ b/tests/data/cases/line_ranges_fmt_off_decorator.py
@@ -1,4 +1,4 @@
-# flags: --line-ranges=12-12
+# flags: --line-ranges=12-12 --line-ranges=21-21
 # NOTE: If you need to modify this file, pay special attention to the --line-ranges=
 # flag above as it's formatting specifically these lines.
 
@@ -11,9 +11,19 @@ class MyClass:
     def method():
         print   ( "str" )
 
+    @decor(
+        a=1,
+        # fmt: off
+        b=(2,   3),
+        # fmt: on
+    )
+    def func():
+          pass
+
+
 # output
 
-# flags: --line-ranges=12-12
+# flags: --line-ranges=12-12 --line-ranges=21-21
 # NOTE: If you need to modify this file, pay special attention to the --line-ranges=
 # flag above as it's formatting specifically these lines.
 
@@ -25,3 +35,13 @@ class MyClass:
     # fmt: on
     def method():
         print("str")
+
+    @decor(
+        a=1,
+        # fmt: off
+        b=(2,   3),
+        # fmt: on
+    )
+    def func():
+        pass
+
diff --git a/tests/data/cases/pep_572_remove_parens.py b/tests/data/cases/pep_572_remove_parens.py
index 24f1ac29168..88774d81649 100644
--- a/tests/data/cases/pep_572_remove_parens.py
+++ b/tests/data/cases/pep_572_remove_parens.py
@@ -1,4 +1,4 @@
-# flags: --minimum-version=3.8
+# flags: --minimum-version=3.8 --no-preview-line-length-1
 if (foo := 0):
     pass
 
diff --git a/tests/data/cases/preview_hug_parens_with_braces_and_square_brackets.py b/tests/data/cases/preview_hug_parens_with_braces_and_square_brackets.py
index 9e5c9eb8546..47a6a0bcae6 100644
--- a/tests/data/cases/preview_hug_parens_with_braces_and_square_brackets.py
+++ b/tests/data/cases/preview_hug_parens_with_braces_and_square_brackets.py
@@ -125,23 +125,6 @@ def foo_square_brackets(request):
 func([x for x in "long line long line long line long line long line long line long line"])
 func([x for x in [x for x in "long line long line long line long line long line long line long line"]])
 
-func({"short line"})
-func({"long line", "long long line", "long long long line", "long long long long line", "long long long long long line"})
-func({{"long line", "long long line", "long long long line", "long long long long line", "long long long long long line"}})
-func(("long line", "long long line", "long long long line", "long long long long line", "long long long long long line"))
-func((("long line", "long long line", "long long long line", "long long long long line", "long long long long long line")))
-func([["long line", "long long line", "long long long line", "long long long long line", "long long long long long line"]])
-
-# Do not hug if the argument fits on a single line.
-func({"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"})
-func(("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"))
-func(["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"])
-func(**{"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit---"})
-func(*("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit----"))
-array = [{"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"}]
-array = [("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line")]
-array = [["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"]]
-
 foooooooooooooooooooo(
     [{c: n + 1 for c in range(256)} for n in range(100)] + [{}], {size}
 )
@@ -151,14 +134,11 @@ def foo_square_brackets(request):
 )
 
 nested_mapping = {"key": [{"a very long key 1": "with a very long value", "a very long key 2": "with a very long value"}]}
-nested_array = [[["long line", "long long line", "long long long line", "long long long long line", "long long long long long line"]]]
 explicit_exploding = [[["short", "line",],],]
 single_item_do_not_explode = Context({
     "version": get_docs_version(),
 })
 
-foo(*["long long long long long line", "long long long long long line", "long long long long long line"])
-
 foo(*[str(i) for i in range(100000000000000000000000000000000000000000000000000000000000)])
 
 foo(
@@ -310,69 +290,6 @@ def foo_square_brackets(request):
     ]
 ])
 
-func({"short line"})
-func({
-    "long line",
-    "long long line",
-    "long long long line",
-    "long long long long line",
-    "long long long long long line",
-})
-func({{
-    "long line",
-    "long long line",
-    "long long long line",
-    "long long long long line",
-    "long long long long long line",
-}})
-func((
-    "long line",
-    "long long line",
-    "long long long line",
-    "long long long long line",
-    "long long long long long line",
-))
-func(((
-    "long line",
-    "long long line",
-    "long long long line",
-    "long long long long line",
-    "long long long long long line",
-)))
-func([[
-    "long line",
-    "long long line",
-    "long long long line",
-    "long long long long line",
-    "long long long long long line",
-]])
-
-# Do not hug if the argument fits on a single line.
-func(
-    {"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"}
-)
-func(
-    ("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line")
-)
-func(
-    ["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"]
-)
-func(
-    **{"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit---"}
-)
-func(
-    *("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit----")
-)
-array = [
-    {"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"}
-]
-array = [
-    ("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line")
-]
-array = [
-    ["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"]
-]
-
 foooooooooooooooooooo(
     [{c: n + 1 for c in range(256)} for n in range(100)] + [{}], {size}
 )
@@ -387,13 +304,6 @@ def foo_square_brackets(request):
         "a very long key 2": "with a very long value",
     }]
 }
-nested_array = [[[
-    "long line",
-    "long long line",
-    "long long long line",
-    "long long long long line",
-    "long long long long long line",
-]]]
 explicit_exploding = [
     [
         [
@@ -406,12 +316,6 @@ def foo_square_brackets(request):
     "version": get_docs_version(),
 })
 
-foo(*[
-    "long long long long long line",
-    "long long long long long line",
-    "long long long long long line",
-])
-
 foo(*[
     str(i) for i in range(100000000000000000000000000000000000000000000000000000000000)
 ])
diff --git a/tests/data/cases/preview_hug_parens_with_braces_and_square_brackets_no_ll1.py b/tests/data/cases/preview_hug_parens_with_braces_and_square_brackets_no_ll1.py
new file mode 100644
index 00000000000..fdebdf69c20
--- /dev/null
+++ b/tests/data/cases/preview_hug_parens_with_braces_and_square_brackets_no_ll1.py
@@ -0,0 +1,106 @@
+# flags: --preview --no-preview-line-length-1
+# split out from preview_hug_parens_with_brackes_and_square_brackets, as it produces
+# different code on the second pass with line-length 1 in many cases.
+# Seems to be about whether the last string in a sequence gets wrapped in parens or not.
+foo(*["long long long long long line", "long long long long long line", "long long long long long line"])
+func({"short line"})
+func({"long line", "long long line", "long long long line", "long long long long line", "long long long long long line"})
+func({{"long line", "long long line", "long long long line", "long long long long line", "long long long long long line"}})
+func(("long line", "long long line", "long long long line", "long long long long line", "long long long long long line"))
+func((("long line", "long long line", "long long long line", "long long long long line", "long long long long long line")))
+func([["long line", "long long line", "long long long line", "long long long long line", "long long long long long line"]])
+
+
+# Do not hug if the argument fits on a single line.
+func({"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"})
+func(("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"))
+func(["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"])
+func(**{"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit---"})
+func(*("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit----"))
+array = [{"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"}]
+array = [("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line")]
+array = [["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"]]
+
+nested_array = [[["long line", "long long line", "long long long line", "long long long long line", "long long long long long line"]]]
+
+# output
+
+# split out from preview_hug_parens_with_brackes_and_square_brackets, as it produces
+# different code on the second pass with line-length 1 in many cases.
+# Seems to be about whether the last string in a sequence gets wrapped in parens or not.
+foo(*[
+    "long long long long long line",
+    "long long long long long line",
+    "long long long long long line",
+])
+func({"short line"})
+func({
+    "long line",
+    "long long line",
+    "long long long line",
+    "long long long long line",
+    "long long long long long line",
+})
+func({{
+    "long line",
+    "long long line",
+    "long long long line",
+    "long long long long line",
+    "long long long long long line",
+}})
+func((
+    "long line",
+    "long long line",
+    "long long long line",
+    "long long long long line",
+    "long long long long long line",
+))
+func(((
+    "long line",
+    "long long line",
+    "long long long line",
+    "long long long long line",
+    "long long long long long line",
+)))
+func([[
+    "long line",
+    "long long line",
+    "long long long line",
+    "long long long long line",
+    "long long long long long line",
+]])
+
+
+# Do not hug if the argument fits on a single line.
+func(
+    {"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"}
+)
+func(
+    ("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line")
+)
+func(
+    ["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"]
+)
+func(
+    **{"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit---"}
+)
+func(
+    *("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit----")
+)
+array = [
+    {"fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"}
+]
+array = [
+    ("fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line")
+]
+array = [
+    ["fit line", "fit line", "fit line", "fit line", "fit line", "fit line", "fit line"]
+]
+
+nested_array = [[[
+    "long line",
+    "long long line",
+    "long long long line",
+    "long long long long line",
+    "long long long long long line",
+]]]
diff --git a/tests/data/cases/preview_prefer_rhs_split.py b/tests/data/cases/preview_prefer_rhs_split.py
index c732c33b53a..28d89c368c0 100644
--- a/tests/data/cases/preview_prefer_rhs_split.py
+++ b/tests/data/cases/preview_prefer_rhs_split.py
@@ -84,3 +84,24 @@
 ) or (
     isinstance(some_other_var, BaseClass) and table.something != table.some_other_thing
 )
+
+# Multiple targets
+a = b = (
+    ccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccc
+)
+
+a = b = c = d = e = f = g = (
+    hhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh
+) = i = j = (
+    kkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkkk
+)
+
+a = (
+    bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
+) = c
+
+a = (
+    bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb
+) = (
+    cccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccccc
+) = ddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddddd
diff --git a/tests/test_format.py b/tests/test_format.py
index 6c2eca8c618..9162c585c08 100644
--- a/tests/test_format.py
+++ b/tests/test_format.py
@@ -30,6 +30,7 @@ def check_file(subdir: str, filename: str, *, data: bool = True) -> None:
         fast=args.fast,
         minimum_version=args.minimum_version,
         lines=args.lines,
+        no_preview_line_length_1=args.no_preview_line_length_1,
     )
     if args.minimum_version is not None:
         major, minor = args.minimum_version
@@ -42,6 +43,7 @@ def check_file(subdir: str, filename: str, *, data: bool = True) -> None:
             fast=args.fast,
             minimum_version=args.minimum_version,
             lines=args.lines,
+            no_preview_line_length_1=args.no_preview_line_length_1,
         )
 
 
diff --git a/tests/util.py b/tests/util.py
index c8699d335ab..9ea30e62fe3 100644
--- a/tests/util.py
+++ b/tests/util.py
@@ -46,6 +46,7 @@ class TestCaseArgs:
     fast: bool = False
     minimum_version: Optional[Tuple[int, int]] = None
     lines: Collection[Tuple[int, int]] = ()
+    no_preview_line_length_1: bool = False
 
 
 def _assert_format_equal(expected: str, actual: str) -> None:
@@ -96,6 +97,7 @@ def assert_format(
     fast: bool = False,
     minimum_version: Optional[Tuple[int, int]] = None,
     lines: Collection[Tuple[int, int]] = (),
+    no_preview_line_length_1: bool = False,
 ) -> None:
     """Convenience function to check that Black formats as expected.
 
@@ -124,21 +126,28 @@ def assert_format(
             f"Black crashed formatting this case in {text} mode."
         ) from e
     # Similarly, setting line length to 1 is a good way to catch
-    # stability bugs. But only in non-preview mode because preview mode
-    # currently has a lot of line length 1 bugs.
-    try:
-        _assert_format_inner(
-            source,
-            None,
-            replace(mode, preview=False, line_length=1),
-            fast=fast,
-            minimum_version=minimum_version,
-            lines=lines,
-        )
-    except Exception as e:
-        raise FormatFailure(
-            "Black crashed formatting this case with line-length set to 1."
-        ) from e
+    # stability bugs. Some tests are known to be broken in preview mode with line length
+    # of 1 though, and have marked that with a flag --no-preview-line-length-1
+    preview_modes = [False]
+    if not no_preview_line_length_1:
+        preview_modes.append(True)
+
+    for preview_mode in preview_modes:
+
+        try:
+            _assert_format_inner(
+                source,
+                None,
+                replace(mode, preview=preview_mode, line_length=1),
+                fast=fast,
+                minimum_version=minimum_version,
+                lines=lines,
+            )
+        except Exception as e:
+            text = "preview" if preview_mode else "non-preview"
+            raise FormatFailure(
+                f"Black crashed formatting this case in {text} mode with line-length=1."
+            ) from e
 
 
 def _assert_format_inner(
@@ -246,6 +255,15 @@ def get_flags_parser() -> argparse.ArgumentParser:
         ),
     )
     parser.add_argument("--line-ranges", action="append")
+    parser.add_argument(
+        "--no-preview-line-length-1",
+        default=False,
+        action="store_true",
+        help=(
+            "Don't run in preview mode with --line-length=1, as that's known to cause a"
+            " crash"
+        ),
+    )
     return parser
 
 
@@ -266,7 +284,11 @@ def parse_mode(flags_line: str) -> TestCaseArgs:
     else:
         lines = []
     return TestCaseArgs(
-        mode=mode, fast=args.fast, minimum_version=args.minimum_version, lines=lines
+        mode=mode,
+        fast=args.fast,
+        minimum_version=args.minimum_version,
+        lines=lines,
+        no_preview_line_length_1=args.no_preview_line_length_1,
     )