diff --git a/src/attr.rs b/src/attr.rs
index 2679b1b6e7a..802dfc0485c 100644
--- a/src/attr.rs
+++ b/src/attr.rs
@@ -11,7 +11,7 @@ use crate::config::IndentStyle;
 use crate::expr::rewrite_literal;
 use crate::lists::{definitive_tactic, itemize_list, write_list, ListFormatting, Separator};
 use crate::overflow;
-use crate::rewrite::{Rewrite, RewriteContext, RewriteErrorExt};
+use crate::rewrite::{Rewrite, RewriteContext, RewriteError, RewriteErrorExt, RewriteResult};
 use crate::shape::Shape;
 use crate::source_map::SpanUtils;
 use crate::types::{rewrite_path, PathContext};
@@ -217,9 +217,9 @@ fn rewrite_initial_doc_comments(
     context: &RewriteContext<'_>,
     attrs: &[ast::Attribute],
     shape: Shape,
-) -> Option<(usize, Option<String>)> {
+) -> Result<(usize, Option<String>), RewriteError> {
     if attrs.is_empty() {
-        return Some((0, None));
+        return Ok((0, None));
     }
     // Rewrite doc comments
     let sugared_docs = take_while_with_pred(context, attrs, |a| a.is_doc_comment());
@@ -229,7 +229,7 @@ fn rewrite_initial_doc_comments(
             .map(|a| context.snippet(a.span))
             .collect::<Vec<_>>()
             .join("\n");
-        return Some((
+        return Ok((
             sugared_docs.len(),
             Some(rewrite_doc_comment(
                 &snippet,
@@ -239,13 +239,19 @@ fn rewrite_initial_doc_comments(
         ));
     }
 
-    Some((0, None))
+    Ok((0, None))
 }
 
 impl Rewrite for ast::NestedMetaItem {
     fn rewrite(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
+        self.rewrite_result(context, shape).ok()
+    }
+
+    fn rewrite_result(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
         match self {
-            ast::NestedMetaItem::MetaItem(ref meta_item) => meta_item.rewrite(context, shape),
+            ast::NestedMetaItem::MetaItem(ref meta_item) => {
+                meta_item.rewrite_result(context, shape)
+            }
             ast::NestedMetaItem::Lit(ref l) => {
                 rewrite_literal(context, l.as_token_lit(), l.span, shape)
             }
@@ -277,11 +283,7 @@ impl Rewrite for ast::MetaItem {
         self.rewrite_result(context, shape).ok()
     }
 
-    fn rewrite_result(
-        &self,
-        context: &RewriteContext<'_>,
-        shape: Shape,
-    ) -> crate::rewrite::RewriteResult {
+    fn rewrite_result(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
         Ok(match self.kind {
             ast::MetaItemKind::Word => {
                 rewrite_path(context, PathContext::Type, &None, &self.path, shape)?
@@ -317,7 +319,7 @@ impl Rewrite for ast::MetaItem {
                 // is longer than the max width and continue on formatting.
                 // See #2479 for example.
                 let value = rewrite_literal(context, lit.as_token_lit(), lit.span, lit_shape)
-                    .unwrap_or_else(|| context.snippet(lit.span).to_owned());
+                    .unwrap_or_else(|_| context.snippet(lit.span).to_owned());
                 format!("{path} = {value}")
             }
         })
@@ -326,6 +328,10 @@ impl Rewrite for ast::MetaItem {
 
 impl Rewrite for ast::Attribute {
     fn rewrite(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
+        self.rewrite_result(context, shape).ok()
+    }
+
+    fn rewrite_result(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
         let snippet = context.snippet(self.span);
         if self.is_doc_comment() {
             rewrite_doc_comment(snippet, shape.comment(context.config), context.config)
@@ -337,7 +343,7 @@ impl Rewrite for ast::Attribute {
             let prefix = attr_prefix(self);
 
             if should_skip || contains_comment(snippet) {
-                return Some(snippet.to_owned());
+                return Ok(snippet.to_owned());
             }
 
             if let Some(ref meta) = self.meta() {
@@ -362,9 +368,11 @@ impl Rewrite for ast::Attribute {
                 }
 
                 // 1 = `[`
-                let shape = shape.offset_left(prefix.len() + 1)?;
-                Some(meta.rewrite(context, shape).map_or_else(
-                    || snippet.to_owned(),
+                let shape = shape
+                    .offset_left(prefix.len() + 1)
+                    .max_width_error(shape.width, self.span)?;
+                Ok(meta.rewrite_result(context, shape).map_or_else(
+                    |_| snippet.to_owned(),
                     |rw| match &self.kind {
                         ast::AttrKind::Normal(normal_attr) => match normal_attr.item.unsafety {
                             // For #![feature(unsafe_attributes)]
@@ -376,7 +384,7 @@ impl Rewrite for ast::Attribute {
                     },
                 ))
             } else {
-                Some(snippet.to_owned())
+                Ok(snippet.to_owned())
             }
         }
     }
@@ -384,8 +392,12 @@ impl Rewrite for ast::Attribute {
 
 impl Rewrite for [ast::Attribute] {
     fn rewrite(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
+        self.rewrite_result(context, shape).ok()
+    }
+
+    fn rewrite_result(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
         if self.is_empty() {
-            return Some(String::new());
+            return Ok(String::new());
         }
 
         // The current remaining attributes.
@@ -401,7 +413,7 @@ impl Rewrite for [ast::Attribute] {
         // merging derives into a single attribute.
         loop {
             if attrs.is_empty() {
-                return Some(result);
+                return Ok(result);
             }
 
             // Handle doc comments.
@@ -440,7 +452,7 @@ impl Rewrite for [ast::Attribute] {
             // Handle derives if we will merge them.
             if !skip_derives && context.config.merge_derives() && is_derive(&attrs[0]) {
                 let derives = take_while_with_pred(context, attrs, is_derive);
-                let derive_str = format_derive(derives, shape, context)?;
+                let derive_str = format_derive(derives, shape, context).unknown_error()?;
                 result.push_str(&derive_str);
 
                 let missing_span = attrs
@@ -473,7 +485,7 @@ impl Rewrite for [ast::Attribute] {
             // If we get here, then we have a regular attribute, just handle one
             // at a time.
 
-            let formatted_attr = attrs[0].rewrite(context, shape)?;
+            let formatted_attr = attrs[0].rewrite_result(context, shape)?;
             result.push_str(&formatted_attr);
 
             let missing_span = attrs
diff --git a/src/chains.rs b/src/chains.rs
index 923ffeae7b7..65326527000 100644
--- a/src/chains.rs
+++ b/src/chains.rs
@@ -66,7 +66,7 @@ use crate::config::{IndentStyle, StyleEdition};
 use crate::expr::rewrite_call;
 use crate::lists::extract_pre_comment;
 use crate::macros::convert_try_mac;
-use crate::rewrite::{Rewrite, RewriteContext, RewriteError, RewriteResult};
+use crate::rewrite::{Rewrite, RewriteContext, RewriteError, RewriteErrorExt, RewriteResult};
 use crate::shape::Shape;
 use crate::source_map::SpanUtils;
 use crate::utils::{
@@ -268,7 +268,13 @@ impl ChainItemKind {
 
 impl Rewrite for ChainItem {
     fn rewrite(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
-        let shape = shape.sub_width(self.tries)?;
+        self.rewrite_result(context, shape).ok()
+    }
+
+    fn rewrite_result(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
+        let shape = shape
+            .sub_width(self.tries)
+            .max_width_error(shape.width, self.span)?;
         let rewrite = match self.kind {
             ChainItemKind::Parent {
                 ref expr,
@@ -277,10 +283,9 @@ impl Rewrite for ChainItem {
             ChainItemKind::Parent {
                 ref expr,
                 parens: false,
-            } => expr.rewrite(context, shape)?,
+            } => expr.rewrite_result(context, shape)?,
             ChainItemKind::MethodCall(ref segment, ref types, ref exprs) => {
-                Self::rewrite_method_call(segment.ident, types, exprs, self.span, context, shape)
-                    .ok()?
+                Self::rewrite_method_call(segment.ident, types, exprs, self.span, context, shape)?
             }
             ChainItemKind::StructField(ident) => format!(".{}", rewrite_ident(context, ident)),
             ChainItemKind::TupleField(ident, nested) => format!(
@@ -297,7 +302,7 @@ impl Rewrite for ChainItem {
                 rewrite_comment(comment, false, shape, context.config)?
             }
         };
-        Some(format!("{rewrite}{}", "?".repeat(self.tries)))
+        Ok(format!("{rewrite}{}", "?".repeat(self.tries)))
     }
 }
 
diff --git a/src/comment.rs b/src/comment.rs
index 24a5a1be2c3..5bf3c1a725c 100644
--- a/src/comment.rs
+++ b/src/comment.rs
@@ -6,7 +6,7 @@ use itertools::{multipeek, MultiPeek};
 use rustc_span::Span;
 
 use crate::config::Config;
-use crate::rewrite::RewriteContext;
+use crate::rewrite::{RewriteContext, RewriteErrorExt, RewriteResult};
 use crate::shape::{Indent, Shape};
 use crate::string::{rewrite_string, StringFormat};
 use crate::utils::{
@@ -157,7 +157,7 @@ pub(crate) fn combine_strs_with_missing_comments(
     span: Span,
     shape: Shape,
     allow_extend: bool,
-) -> Option<String> {
+) -> RewriteResult {
     trace!(
         "combine_strs_with_missing_comments `{}` `{}` {:?} {:?}",
         prev_str, next_str, span, shape
@@ -187,7 +187,7 @@ pub(crate) fn combine_strs_with_missing_comments(
             result.push_str(&indent.to_string_with_newline(config))
         }
         result.push_str(next_str);
-        return Some(result);
+        return Ok(result);
     }
 
     // We have a missing comment between the first expression and the second expression.
@@ -232,10 +232,10 @@ pub(crate) fn combine_strs_with_missing_comments(
     result.push_str(&second_sep);
     result.push_str(next_str);
 
-    Some(result)
+    Ok(result)
 }
 
-pub(crate) fn rewrite_doc_comment(orig: &str, shape: Shape, config: &Config) -> Option<String> {
+pub(crate) fn rewrite_doc_comment(orig: &str, shape: Shape, config: &Config) -> RewriteResult {
     identify_comment(orig, false, shape, config, true)
 }
 
@@ -244,7 +244,7 @@ pub(crate) fn rewrite_comment(
     block_style: bool,
     shape: Shape,
     config: &Config,
-) -> Option<String> {
+) -> RewriteResult {
     identify_comment(orig, block_style, shape, config, false)
 }
 
@@ -254,7 +254,7 @@ fn identify_comment(
     shape: Shape,
     config: &Config,
     is_doc_comment: bool,
-) -> Option<String> {
+) -> RewriteResult {
     let style = comment_style(orig, false);
 
     // Computes the byte length of line taking into account a newline if the line is part of a
@@ -346,7 +346,7 @@ fn identify_comment(
     let (first_group, rest) = orig.split_at(first_group_ending);
     let rewritten_first_group =
         if !config.normalize_comments() && has_bare_lines && style.is_block_comment() {
-            trim_left_preserve_layout(first_group, shape.indent, config)?
+            trim_left_preserve_layout(first_group, shape.indent, config).unknown_error()?
         } else if !config.normalize_comments()
             && !config.wrap_comments()
             && !(
@@ -367,7 +367,7 @@ fn identify_comment(
             )?
         };
     if rest.is_empty() {
-        Some(rewritten_first_group)
+        Ok(rewritten_first_group)
     } else {
         identify_comment(
             rest.trim_start(),
@@ -899,7 +899,7 @@ fn rewrite_comment_inner(
     shape: Shape,
     config: &Config,
     is_doc_comment: bool,
-) -> Option<String> {
+) -> RewriteResult {
     let mut rewriter = CommentRewrite::new(orig, block_style, shape, config);
 
     let line_breaks = count_newlines(orig.trim_end());
@@ -933,7 +933,7 @@ fn rewrite_comment_inner(
         }
     }
 
-    Some(rewriter.finish())
+    Ok(rewriter.finish())
 }
 
 const RUSTFMT_CUSTOM_COMMENT_PREFIX: &str = "//#### ";
@@ -998,7 +998,7 @@ pub(crate) fn rewrite_missing_comment(
     span: Span,
     shape: Shape,
     context: &RewriteContext<'_>,
-) -> Option<String> {
+) -> RewriteResult {
     let missing_snippet = context.snippet(span);
     let trimmed_snippet = missing_snippet.trim();
     // check the span starts with a comment
@@ -1006,7 +1006,7 @@ pub(crate) fn rewrite_missing_comment(
     if !trimmed_snippet.is_empty() && pos.is_some() {
         rewrite_comment(trimmed_snippet, false, shape, context.config)
     } else {
-        Some(String::new())
+        Ok(String::new())
     }
 }
 
@@ -1018,13 +1018,13 @@ pub(crate) fn recover_missing_comment_in_span(
     shape: Shape,
     context: &RewriteContext<'_>,
     used_width: usize,
-) -> Option<String> {
+) -> RewriteResult {
     let missing_comment = rewrite_missing_comment(span, shape, context)?;
     if missing_comment.is_empty() {
-        Some(String::new())
+        Ok(String::new())
     } else {
         let missing_snippet = context.snippet(span);
-        let pos = missing_snippet.find('/')?;
+        let pos = missing_snippet.find('/').unknown_error()?;
         // 1 = ` `
         let total_width = missing_comment.len() + used_width + 1;
         let force_new_line_before_comment =
@@ -1034,7 +1034,7 @@ pub(crate) fn recover_missing_comment_in_span(
         } else {
             Cow::from(" ")
         };
-        Some(format!("{sep}{missing_comment}"))
+        Ok(format!("{sep}{missing_comment}"))
     }
 }
 
diff --git a/src/expr.rs b/src/expr.rs
index 6f6f9fec6c0..0edc35c7c7d 100644
--- a/src/expr.rs
+++ b/src/expr.rs
@@ -82,7 +82,7 @@ pub(crate) fn format_expr(
         )
         .ok(),
         ast::ExprKind::Lit(token_lit) => {
-            if let Some(expr_rw) = rewrite_literal(context, token_lit, expr.span, shape) {
+            if let Ok(expr_rw) = rewrite_literal(context, token_lit, expr.span, shape) {
                 Some(expr_rw)
             } else {
                 if let LitKind::StrRaw(_) = token_lit.kind {
@@ -97,7 +97,7 @@ pub(crate) fn format_expr(
             let callee_str = callee.rewrite(context, shape)?;
             rewrite_call(context, &callee_str, args, inner_span, shape).ok()
         }
-        ast::ExprKind::Paren(ref subexpr) => rewrite_paren(context, subexpr, shape, expr.span),
+        ast::ExprKind::Paren(ref subexpr) => rewrite_paren(context, subexpr, shape, expr.span).ok(),
         ast::ExprKind::Binary(op, ref lhs, ref rhs) => {
             // FIXME: format comments between operands and operator
             rewrite_all_pairs(expr, shape, context)
@@ -136,7 +136,9 @@ pub(crate) fn format_expr(
         ast::ExprKind::Tup(ref items) => {
             rewrite_tuple(context, items.iter(), expr.span, shape, items.len() == 1).ok()
         }
-        ast::ExprKind::Let(ref pat, ref expr, _span, _) => rewrite_let(context, shape, pat, expr),
+        ast::ExprKind::Let(ref pat, ref expr, _span, _) => {
+            rewrite_let(context, shape, pat, expr).ok()
+        }
         ast::ExprKind::If(..)
         | ast::ExprKind::ForLoop { .. }
         | ast::ExprKind::Loop(..)
@@ -166,7 +168,7 @@ pub(crate) fn format_expr(
                         // Rewrite block without trying to put it in a single line.
                         rw
                     } else {
-                        let prefix = block_prefix(context, block, shape)?;
+                        let prefix = block_prefix(context, block, shape).ok()?;
 
                         rewrite_block_with_visitor(
                             context,
@@ -437,6 +439,7 @@ pub(crate) fn format_expr(
                 expr.span.lo(),
             );
             combine_strs_with_missing_comments(context, &attrs_str, &expr_str, span, shape, false)
+                .ok()
         })
 }
 
@@ -498,17 +501,20 @@ fn rewrite_empty_block(
     None
 }
 
-fn block_prefix(context: &RewriteContext<'_>, block: &ast::Block, shape: Shape) -> Option<String> {
-    Some(match block.rules {
+fn block_prefix(context: &RewriteContext<'_>, block: &ast::Block, shape: Shape) -> RewriteResult {
+    Ok(match block.rules {
         ast::BlockCheckMode::Unsafe(..) => {
             let snippet = context.snippet(block.span);
-            let open_pos = snippet.find_uncommented("{")?;
+            let open_pos = snippet.find_uncommented("{").unknown_error()?;
             // Extract comment between unsafe and block start.
             let trimmed = &snippet[6..open_pos].trim();
 
             if !trimmed.is_empty() {
                 // 9 = "unsafe  {".len(), 7 = "unsafe ".len()
-                let budget = shape.width.checked_sub(9)?;
+                let budget = shape
+                    .width
+                    .checked_sub(9)
+                    .max_width_error(shape.width, block.span)?;
                 format!(
                     "unsafe {} ",
                     rewrite_comment(
@@ -612,7 +618,7 @@ fn rewrite_block_inner(
     context: &RewriteContext<'_>,
     shape: Shape,
 ) -> RewriteResult {
-    let prefix = block_prefix(context, block, shape).unknown_error()?;
+    let prefix = block_prefix(context, block, shape)?;
 
     // shape.width is used only for the single line case: either the empty block `{}`,
     // or an unsafe expression `unsafe { e }`.
@@ -912,7 +918,8 @@ impl<'a> ControlFlow<'a> {
                 RhsTactics::Default,
                 comments_span,
                 true,
-            );
+            )
+            .ok();
         }
 
         let expr_rw = expr.rewrite(context, cond_shape);
@@ -1191,7 +1198,7 @@ fn rewrite_label(opt_label: Option<ast::Label>) -> Cow<'static, str> {
 
 fn extract_comment(span: Span, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
     match rewrite_missing_comment(span, shape, context) {
-        Some(ref comment) if !comment.is_empty() => Some(format!(
+        Ok(ref comment) if !comment.is_empty() => Some(format!(
             "{indent}{comment}{indent}",
             indent = shape.indent.to_string_with_newline(context.config)
         )),
@@ -1262,7 +1269,7 @@ pub(crate) fn rewrite_literal(
     token_lit: token::Lit,
     span: Span,
     shape: Shape,
-) -> Option<String> {
+) -> RewriteResult {
     match token_lit.kind {
         token::LitKind::Str => rewrite_string_lit(context, span, shape),
         token::LitKind::Integer => rewrite_int_lit(context, token_lit, span, shape),
@@ -1270,11 +1277,12 @@ pub(crate) fn rewrite_literal(
             context.snippet(span).to_owned(),
             context.config.max_width(),
             shape,
-        ),
+        )
+        .max_width_error(shape.width, span),
     }
 }
 
-fn rewrite_string_lit(context: &RewriteContext<'_>, span: Span, shape: Shape) -> Option<String> {
+fn rewrite_string_lit(context: &RewriteContext<'_>, span: Span, shape: Shape) -> RewriteResult {
     let string_lit = context.snippet(span);
 
     if !context.config.format_strings() {
@@ -1284,9 +1292,10 @@ fn rewrite_string_lit(context: &RewriteContext<'_>, span: Span, shape: Shape) ->
             .all(|line| line.ends_with('\\'))
             && context.config.style_edition() >= StyleEdition::Edition2024
         {
-            return Some(string_lit.to_owned());
+            return Ok(string_lit.to_owned());
         } else {
-            return wrap_str(string_lit.to_owned(), context.config.max_width(), shape);
+            return wrap_str(string_lit.to_owned(), context.config.max_width(), shape)
+                .max_width_error(shape.width, span);
         }
     }
 
@@ -1298,6 +1307,7 @@ fn rewrite_string_lit(context: &RewriteContext<'_>, span: Span, shape: Shape) ->
         &StringFormat::new(shape.visual_indent(0), context.config),
         shape.width.saturating_sub(2),
     )
+    .max_width_error(shape.width, span)
 }
 
 fn rewrite_int_lit(
@@ -1305,7 +1315,7 @@ fn rewrite_int_lit(
     token_lit: token::Lit,
     span: Span,
     shape: Shape,
-) -> Option<String> {
+) -> RewriteResult {
     let symbol = token_lit.symbol.as_str();
 
     if let Some(symbol_stripped) = symbol.strip_prefix("0x") {
@@ -1323,7 +1333,8 @@ fn rewrite_int_lit(
                 ),
                 context.config.max_width(),
                 shape,
-            );
+            )
+            .max_width_error(shape.width, span);
         }
     }
 
@@ -1332,6 +1343,7 @@ fn rewrite_int_lit(
         context.config.max_width(),
         shape,
     )
+    .max_width_error(shape.width, span)
 }
 
 fn choose_separator_tactic(context: &RewriteContext<'_>, span: Span) -> Option<SeparatorTactic> {
@@ -1472,7 +1484,7 @@ pub(crate) fn rewrite_paren(
     mut subexpr: &ast::Expr,
     shape: Shape,
     mut span: Span,
-) -> Option<String> {
+) -> RewriteResult {
     debug!("rewrite_paren, shape: {:?}", shape);
 
     // Extract comments within parens.
@@ -1501,11 +1513,14 @@ pub(crate) fn rewrite_paren(
     }
 
     // 1 = `(` and `)`
-    let sub_shape = shape.offset_left(1)?.sub_width(1)?;
-    let subexpr_str = subexpr.rewrite(context, sub_shape)?;
+    let sub_shape = shape
+        .offset_left(1)
+        .and_then(|s| s.sub_width(1))
+        .max_width_error(shape.width, span)?;
+    let subexpr_str = subexpr.rewrite_result(context, sub_shape)?;
     let fits_single_line = !pre_comment.contains("//") && !post_comment.contains("//");
     if fits_single_line {
-        Some(format!("({pre_comment}{subexpr_str}{post_comment})"))
+        Ok(format!("({pre_comment}{subexpr_str}{post_comment})"))
     } else {
         rewrite_paren_in_multi_line(context, subexpr, shape, pre_span, post_span)
     }
@@ -1517,12 +1532,12 @@ fn rewrite_paren_in_multi_line(
     shape: Shape,
     pre_span: Span,
     post_span: Span,
-) -> Option<String> {
+) -> RewriteResult {
     let nested_indent = shape.indent.block_indent(context.config);
     let nested_shape = Shape::indented(nested_indent, context.config);
     let pre_comment = rewrite_missing_comment(pre_span, nested_shape, context)?;
     let post_comment = rewrite_missing_comment(post_span, nested_shape, context)?;
-    let subexpr_str = subexpr.rewrite(context, nested_shape)?;
+    let subexpr_str = subexpr.rewrite_result(context, nested_shape)?;
 
     let mut result = String::with_capacity(subexpr_str.len() * 2);
     result.push('(');
@@ -1539,7 +1554,7 @@ fn rewrite_paren_in_multi_line(
     result.push_str(&shape.indent.to_string_with_newline(context.config));
     result.push(')');
 
-    Some(result)
+    Ok(result)
 }
 
 fn rewrite_index(
@@ -1889,14 +1904,16 @@ fn rewrite_let(
     shape: Shape,
     pat: &ast::Pat,
     expr: &ast::Expr,
-) -> Option<String> {
+) -> RewriteResult {
     let mut result = "let ".to_owned();
 
     // TODO(ytmimi) comments could appear between `let` and the `pat`
 
     // 4 = "let ".len()
-    let pat_shape = shape.offset_left(4)?;
-    let pat_str = pat.rewrite(context, pat_shape)?;
+    let pat_shape = shape
+        .offset_left(4)
+        .max_width_error(shape.width, pat.span)?;
+    let pat_str = pat.rewrite_result(context, pat_shape)?;
     result.push_str(&pat_str);
 
     // TODO(ytmimi) comments could appear between `pat` and `=`
@@ -2116,7 +2133,7 @@ pub(crate) fn rewrite_assign_rhs_with<S: Into<String>, R: Rewrite>(
     Some(lhs + &rhs)
 }
 
-pub(crate) fn rewrite_assign_rhs_with_comments<S: Into<String>, R: Rewrite>(
+pub(crate) fn rewrite_assign_rhs_with_comments<S: Into<String>, R: Rewrite + Spanned>(
     context: &RewriteContext<'_>,
     lhs: S,
     ex: &R,
@@ -2125,21 +2142,23 @@ pub(crate) fn rewrite_assign_rhs_with_comments<S: Into<String>, R: Rewrite>(
     rhs_tactics: RhsTactics,
     between_span: Span,
     allow_extend: bool,
-) -> Option<String> {
+) -> RewriteResult {
     let lhs = lhs.into();
     let contains_comment = contains_comment(context.snippet(between_span));
     let shape = if contains_comment {
-        shape.block_left(context.config.tab_spaces())?
+        shape
+            .block_left(context.config.tab_spaces())
+            .max_width_error(shape.width, between_span.with_hi(ex.span().hi()))?
     } else {
         shape
     };
-    let rhs = rewrite_assign_rhs_expr(context, &lhs, ex, shape, rhs_kind, rhs_tactics)?;
-
+    let rhs =
+        rewrite_assign_rhs_expr(context, &lhs, ex, shape, rhs_kind, rhs_tactics).unknown_error()?;
     if contains_comment {
         let rhs = rhs.trim_start();
         combine_strs_with_missing_comments(context, &lhs, rhs, between_span, shape, allow_extend)
     } else {
-        Some(lhs + &rhs)
+        Ok(lhs + &rhs)
     }
 }
 
diff --git a/src/imports.rs b/src/imports.rs
index edea5230890..6041f678cea 100644
--- a/src/imports.rs
+++ b/src/imports.rs
@@ -367,6 +367,7 @@ impl UseTree {
                     shape,
                     allow_extend,
                 )
+                .ok()
             }
             _ => Some(use_str),
         }
diff --git a/src/items.rs b/src/items.rs
index 6fb6d081946..35591df0fd8 100644
--- a/src/items.rs
+++ b/src/items.rs
@@ -77,8 +77,7 @@ impl Rewrite for ast::Local {
                 ),
                 shape,
                 false,
-            )
-            .unknown_error()?
+            )?
         };
         let let_kw_offset = result.len() - "let ".len();
 
@@ -718,6 +717,7 @@ impl<'a> FmtVisitor<'a> {
         };
 
         combine_strs_with_missing_comments(&context, &attrs_str, &variant_body, span, shape, false)
+            .ok()
     }
 
     fn visit_impl_items(&mut self, items: &[ptr::P<ast::AssocItem>]) {
@@ -853,7 +853,7 @@ pub(crate) fn format_impl(
                 context,
                 last_line_width(&result),
             ) {
-                Some(ref missing_comment) if !missing_comment.is_empty() => {
+                Ok(ref missing_comment) if !missing_comment.is_empty() => {
                     result.push_str(missing_comment);
                 }
                 _ => (),
@@ -1260,7 +1260,7 @@ pub(crate) fn format_trait(
                     context,
                     last_line_width(&result),
                 ) {
-                    Some(ref missing_comment) if !missing_comment.is_empty() => {
+                    Ok(ref missing_comment) if !missing_comment.is_empty() => {
                         result.push_str(missing_comment);
                     }
                     _ => (),
@@ -1550,8 +1550,8 @@ fn format_empty_struct_or_tuple(
     // indented shape for proper indenting of multi-line comments
     let shape = Shape::indented(offset.block_indent(context.config), context.config);
     match rewrite_missing_comment(span, shape, context) {
-        Some(ref s) if s.is_empty() => (),
-        Some(ref s) => {
+        Ok(ref s) if s.is_empty() => (),
+        Ok(ref s) => {
             let is_multi_line = !is_single_line(s);
             if is_multi_line || first_line_contains_single_line_comment(s) {
                 let nested_indent_str = offset
@@ -1564,7 +1564,7 @@ fn format_empty_struct_or_tuple(
                 result.push_str(&offset.to_string_with_newline(context.config));
             }
         }
-        None => result.push_str(context.snippet(span)),
+        Err(_) => result.push_str(context.snippet(span)),
     }
     result.push_str(closer);
 }
@@ -1827,7 +1827,8 @@ fn rewrite_ty<R: Rewrite>(
                     comment_span,
                     comment_shape,
                     true,
-                )?
+                )
+                .ok()?
             }
             _ => format!("{result}="),
         };
@@ -1907,8 +1908,7 @@ pub(crate) fn rewrite_struct_field(
         missing_span,
         shape,
         attrs_extendable,
-    )
-    .unknown_error()?;
+    )?;
     let overhead = trimmed_last_line_width(&attr_prefix);
     let lhs_offset = lhs_max_width.saturating_sub(overhead);
     for _ in 0..lhs_offset {
@@ -1940,7 +1940,6 @@ pub(crate) fn rewrite_struct_field(
         &field_str
     };
     combine_strs_with_missing_comments(context, &attrs_str, field_str, missing_span, shape, false)
-        .unknown_error()
 }
 
 pub(crate) struct StaticParts<'a> {
@@ -2074,6 +2073,7 @@ fn rewrite_static(
             comments_span,
             true,
         )
+        .ok()
         .and_then(|res| recover_comment_removed(res, static_parts.span, context))
         .map(|s| if s.ends_with(';') { s } else { s + ";" })
     } else {
@@ -2170,9 +2170,11 @@ fn get_missing_param_comments(
     };
 
     let comment_before_colon = rewrite_missing_comment(span_before_colon, shape, context)
+        .ok()
         .filter(|comment| !comment.is_empty())
         .map_or(String::new(), |comment| format!(" {}", comment));
     let comment_after_colon = rewrite_missing_comment(span_after_colon, shape, context)
+        .ok()
         .filter(|comment| !comment.is_empty())
         .map_or(String::new(), |comment| format!("{} ", comment));
     (comment_before_colon, comment_after_colon)
@@ -2220,8 +2222,7 @@ impl Rewrite for ast::Param {
                 span,
                 shape,
                 !has_multiple_attr_lines && !has_doc_comments,
-            )
-            .unknown_error()?;
+            )?;
 
             if !is_empty_infer(&*self.ty, self.pat.span) {
                 let (before_comment, after_comment) =
@@ -2253,8 +2254,7 @@ impl Rewrite for ast::Param {
                         span,
                         shape,
                         !has_multiple_attr_lines,
-                    )
-                    .unknown_error()?;
+                    )?;
                     result.push_str(&before_comment);
                     result.push_str(colon_spaces(context.config));
                     result.push_str(&after_comment);
@@ -2301,8 +2301,7 @@ fn rewrite_explicit_self(
                         span,
                         shape,
                         !has_multiple_attr_lines,
-                    )
-                    .unknown_error()?)
+                    )?)
                 }
                 None => Ok(combine_strs_with_missing_comments(
                     context,
@@ -2311,8 +2310,7 @@ fn rewrite_explicit_self(
                     span,
                     shape,
                     !has_multiple_attr_lines,
-                )
-                .unknown_error()?),
+                )?),
             }
         }
         ast::SelfKind::Explicit(ref ty, mutability) => {
@@ -2328,8 +2326,7 @@ fn rewrite_explicit_self(
                 span,
                 shape,
                 !has_multiple_attr_lines,
-            )
-            .unknown_error()?)
+            )?)
         }
         ast::SelfKind::Value(mutability) => Ok(combine_strs_with_missing_comments(
             context,
@@ -2338,8 +2335,7 @@ fn rewrite_explicit_self(
             span,
             shape,
             !has_multiple_attr_lines,
-        )
-        .unknown_error()?),
+        )?),
     }
 }
 
@@ -2677,7 +2673,7 @@ fn rewrite_fn_base(
                 context,
                 last_line_width(&result),
             ) {
-                Some(ref missing_comment) if !missing_comment.is_empty() => {
+                Ok(ref missing_comment) if !missing_comment.is_empty() => {
                     result.push_str(missing_comment);
                     force_new_line_for_brace = true;
                 }
@@ -3201,12 +3197,13 @@ fn rewrite_comments_before_after_where(
     span_after_where: Span,
     shape: Shape,
 ) -> Option<(String, String)> {
-    let before_comment = rewrite_missing_comment(span_before_where, shape, context)?;
+    let before_comment = rewrite_missing_comment(span_before_where, shape, context).ok()?;
     let after_comment = rewrite_missing_comment(
         span_after_where,
         shape.block_indent(context.config.tab_spaces()),
         context,
-    )?;
+    )
+    .ok()?;
     Some((before_comment, after_comment))
 }
 
@@ -3229,7 +3226,7 @@ fn format_header(
         .opt_span_before(mk_sp(vis.span.lo(), ident.span.hi()), item_name.trim())
     {
         let missing_span = mk_sp(after_vis, before_item_name);
-        if let Some(result_with_comment) = combine_strs_with_missing_comments(
+        if let Ok(result_with_comment) = combine_strs_with_missing_comments(
             context,
             &result,
             item_name,
@@ -3313,7 +3310,8 @@ fn format_generics(
                 ),
                 shape,
                 context,
-            ),
+            )
+            .ok(),
         )
     };
     // add missing comments
@@ -3446,6 +3444,7 @@ impl Rewrite for ast::ForeignItem {
             shape,
             false,
         )
+        .ok()
     }
 }
 
@@ -3481,6 +3480,7 @@ fn rewrite_attrs(
         shape,
         allow_extend,
     )
+    .ok()
 }
 
 /// Rewrite an inline mod.
diff --git a/src/lists.rs b/src/lists.rs
index 46d40fa750e..f9e722130cd 100644
--- a/src/lists.rs
+++ b/src/lists.rs
@@ -8,7 +8,7 @@ use rustc_span::BytePos;
 use crate::comment::{find_comment_end, rewrite_comment, FindUncommented};
 use crate::config::lists::*;
 use crate::config::{Config, IndentStyle};
-use crate::rewrite::{RewriteContext, RewriteError, RewriteErrorExt, RewriteResult};
+use crate::rewrite::{RewriteContext, RewriteError, RewriteResult};
 use crate::shape::{Indent, Shape};
 use crate::utils::{
     count_newlines, first_line_width, last_line_width, mk_sp, starts_with_newline,
@@ -366,8 +366,8 @@ where
             // Block style in non-vertical mode.
             let block_mode = tactic == DefinitiveListTactic::Horizontal;
             // Width restriction is only relevant in vertical mode.
-            let comment = rewrite_comment(comment, block_mode, formatting.shape, formatting.config)
-                .unknown_error()?;
+            let comment =
+                rewrite_comment(comment, block_mode, formatting.shape, formatting.config)?;
             result.push_str(&comment);
 
             if !inner_item.is_empty() {
@@ -413,8 +413,7 @@ where
                 true,
                 Shape::legacy(formatting.shape.width, Indent::empty()),
                 formatting.config,
-            )
-            .unknown_error()?;
+            )?;
 
             result.push(' ');
             result.push_str(&formatted_comment);
@@ -465,8 +464,7 @@ where
                 )
             };
 
-            let mut formatted_comment =
-                rewrite_post_comment(&mut item_max_width).unknown_error()?;
+            let mut formatted_comment = rewrite_post_comment(&mut item_max_width)?;
 
             if !starts_with_newline(comment) {
                 if formatting.align_comments {
@@ -479,8 +477,7 @@ where
                         > formatting.config.max_width()
                     {
                         item_max_width = None;
-                        formatted_comment =
-                            rewrite_post_comment(&mut item_max_width).unknown_error()?;
+                        formatted_comment = rewrite_post_comment(&mut item_max_width)?;
                         comment_alignment =
                             post_comment_alignment(item_max_width, unicode_str_width(inner_item));
                     }
diff --git a/src/matches.rs b/src/matches.rs
index 5cb34f54f6e..0a6fada5cb3 100644
--- a/src/matches.rs
+++ b/src/matches.rs
@@ -310,8 +310,7 @@ fn rewrite_match_arm(
         missing_span,
         shape,
         false,
-    )
-    .unknown_error()?;
+    )?;
 
     let arrow_span = mk_sp(
         arm.pat.span.hi(),
@@ -448,7 +447,7 @@ fn rewrite_match_body(
         if comment_str.is_empty() {
             String::new()
         } else {
-            rewrite_comment(comment_str, false, shape, context.config).unknown_error()?
+            rewrite_comment(comment_str, false, shape, context.config)?
         }
     };
 
diff --git a/src/missed_spans.rs b/src/missed_spans.rs
index fc5daf71d16..4d947328bf7 100644
--- a/src/missed_spans.rs
+++ b/src/missed_spans.rs
@@ -284,13 +284,13 @@ impl<'a> FmtVisitor<'a> {
                     let other_lines = &subslice[offset + 1..];
                     let comment_str =
                         rewrite_comment(other_lines, false, comment_shape, self.config)
-                            .unwrap_or_else(|| String::from(other_lines));
+                            .unwrap_or_else(|_| String::from(other_lines));
                     self.push_str(&comment_str);
                 }
             }
         } else {
             let comment_str = rewrite_comment(subslice, false, comment_shape, self.config)
-                .unwrap_or_else(|| String::from(subslice));
+                .unwrap_or_else(|_| String::from(subslice));
             self.push_str(&comment_str);
         }
 
diff --git a/src/patterns.rs b/src/patterns.rs
index 6ec083443bd..f2fbb3c2439 100644
--- a/src/patterns.rs
+++ b/src/patterns.rs
@@ -133,7 +133,8 @@ impl Rewrite for Pat {
                             mk_sp(lo, p.span.lo()),
                             shape,
                             true,
-                        )?
+                        )
+                        .ok()?
                     }
                     None => "".to_owned(),
                 };
@@ -152,7 +153,8 @@ impl Rewrite for Pat {
                                 mk_sp(lo, hi),
                                 shape,
                                 true,
-                            )?,
+                            )
+                            .ok()?,
                         )
                     }
                     (false, true) => (
@@ -181,7 +183,8 @@ impl Rewrite for Pat {
                                 mk_sp(lo, hi),
                                 shape,
                                 true,
-                            )?,
+                            )
+                            .ok()?,
                         )
                     }
                     (false, true) => (first_lo, first),
@@ -198,7 +201,8 @@ impl Rewrite for Pat {
                         mk_sp(ident.span.hi(), hi),
                         shape,
                         true,
-                    )?
+                    )
+                    .ok()?
                 } else {
                     id_str.to_owned()
                 };
@@ -211,6 +215,7 @@ impl Rewrite for Pat {
                     shape,
                     true,
                 )
+                .ok()
             }
             PatKind::Wild => {
                 if 1 <= shape.width {
@@ -408,6 +413,10 @@ fn rewrite_struct_pat(
 
 impl Rewrite for PatField {
     fn rewrite(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
+        self.rewrite_result(context, shape).ok()
+    }
+
+    fn rewrite_result(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
         let hi_pos = if let Some(last) = self.attrs.last() {
             last.span.hi()
         } else {
@@ -417,10 +426,10 @@ impl Rewrite for PatField {
         let attrs_str = if self.attrs.is_empty() {
             String::from("")
         } else {
-            self.attrs.rewrite(context, shape)?
+            self.attrs.rewrite_result(context, shape)?
         };
 
-        let pat_str = self.pat.rewrite(context, shape)?;
+        let pat_str = self.pat.rewrite_result(context, shape)?;
         if self.is_shorthand {
             combine_strs_with_missing_comments(
                 context,
@@ -441,7 +450,7 @@ impl Rewrite for PatField {
                     "{}:\n{}{}",
                     id_str,
                     nested_shape.indent.to_string(context.config),
-                    self.pat.rewrite(context, nested_shape)?
+                    self.pat.rewrite_result(context, nested_shape)?
                 )
             };
             combine_strs_with_missing_comments(
diff --git a/src/types.rs b/src/types.rs
index 1c5a168b42e..676041ffa7a 100644
--- a/src/types.rs
+++ b/src/types.rs
@@ -713,8 +713,7 @@ impl Rewrite for ast::GenericParam {
                 mk_sp(last_attr.span.hi(), param_start),
                 shape,
                 !last_attr.is_doc_comment(),
-            )
-            .unknown_error()?;
+            )?;
         } else {
             // When rewriting generic params, an extra newline should be put
             // if the attributes end with a doc comment
@@ -831,8 +830,7 @@ impl Rewrite for ast::Ty {
                             before_lt_span,
                             shape,
                             true,
-                        )
-                        .unknown_error()?;
+                        )?;
                     } else {
                         result.push_str(&lt_str);
                     }
@@ -851,8 +849,7 @@ impl Rewrite for ast::Ty {
                             before_mut_span,
                             shape,
                             true,
-                        )
-                        .unknown_error()?;
+                        )?;
                     } else {
                         result.push_str(mut_str);
                     }
@@ -868,8 +865,7 @@ impl Rewrite for ast::Ty {
                         before_ty_span,
                         shape,
                         true,
-                    )
-                    .unknown_error()?;
+                    )?;
                 } else {
                     let used_width = last_line_width(&result);
                     let budget = shape
@@ -1182,8 +1178,7 @@ fn join_bounds_inner(
                         is_bound_extendable(bound_str, item),
                         combine_strs_with_missing_comments(
                             context, joiner, bound_str, ls, shape, true,
-                        )
-                        .unknown_error()?,
+                        )?,
                     ),
                     _ => (
                         is_bound_extendable(bound_str, item),
@@ -1200,7 +1195,6 @@ fn join_bounds_inner(
                     shape,
                     true,
                 )
-                .unknown_error()
                 .map(|v| (v, trailing_span, extendable)),
                 _ => Ok((strs + &trailing_str, trailing_span, extendable)),
             }
diff --git a/src/vertical.rs b/src/vertical.rs
index 670fa5a21e4..80c46da4620 100644
--- a/src/vertical.rs
+++ b/src/vertical.rs
@@ -24,7 +24,7 @@ use crate::utils::{
 pub(crate) trait AlignedItem {
     fn skip(&self) -> bool;
     fn get_span(&self) -> Span;
-    fn rewrite_prefix(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String>;
+    fn rewrite_prefix(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult;
     fn rewrite_aligned_item(
         &self,
         context: &RewriteContext<'_>,
@@ -42,15 +42,15 @@ impl AlignedItem for ast::FieldDef {
         self.span()
     }
 
-    fn rewrite_prefix(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
-        let attrs_str = self.attrs.rewrite(context, shape)?;
+    fn rewrite_prefix(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
+        let attrs_str = self.attrs.rewrite_result(context, shape)?;
         let missing_span = if self.attrs.is_empty() {
             mk_sp(self.span.lo(), self.span.lo())
         } else {
             mk_sp(self.attrs.last().unwrap().span.hi(), self.span.lo())
         };
         let attrs_extendable = self.ident.is_none() && is_attributes_extendable(&attrs_str);
-        let field_str = rewrite_struct_field_prefix(context, self).ok()?;
+        let field_str = rewrite_struct_field_prefix(context, self)?;
         combine_strs_with_missing_comments(
             context,
             &attrs_str,
@@ -80,8 +80,8 @@ impl AlignedItem for ast::ExprField {
         self.span()
     }
 
-    fn rewrite_prefix(&self, context: &RewriteContext<'_>, shape: Shape) -> Option<String> {
-        let attrs_str = self.attrs.rewrite(context, shape)?;
+    fn rewrite_prefix(&self, context: &RewriteContext<'_>, shape: Shape) -> RewriteResult {
+        let attrs_str = self.attrs.rewrite_result(context, shape)?;
         let name = rewrite_ident(context, self.ident);
         let missing_span = if self.attrs.is_empty() {
             mk_sp(self.span.lo(), self.span.lo())
@@ -198,7 +198,7 @@ fn struct_field_prefix_max_min_width<T: AlignedItem>(
                 .rewrite_prefix(context, shape)
                 .map(|field_str| trimmed_last_line_width(&field_str))
         })
-        .fold_options((0, ::std::usize::MAX), |(max_len, min_len), len| {
+        .fold_ok((0, ::std::usize::MAX), |(max_len, min_len), len| {
             (cmp::max(max_len, len), cmp::min(min_len, len))
         })
         .unwrap_or((0, 0))
diff --git a/src/visitor.rs b/src/visitor.rs
index 0df3d16e0cb..b08aa35f8f8 100644
--- a/src/visitor.rs
+++ b/src/visitor.rs
@@ -312,8 +312,8 @@ impl<'b, 'a: 'b> FmtVisitor<'a> {
                                 let comment_str =
                                     rewrite_comment(other_lines, false, comment_shape, config);
                                 match comment_str {
-                                    Some(ref s) => self.push_str(s),
-                                    None => self.push_str(other_lines),
+                                    Ok(ref s) => self.push_str(s),
+                                    Err(_) => self.push_str(other_lines),
                                 }
                             }
                         }
@@ -342,8 +342,8 @@ impl<'b, 'a: 'b> FmtVisitor<'a> {
 
                         let comment_str = rewrite_comment(&sub_slice, false, comment_shape, config);
                         match comment_str {
-                            Some(ref s) => self.push_str(s),
-                            None => self.push_str(&sub_slice),
+                            Ok(ref s) => self.push_str(s),
+                            Err(_) => self.push_str(&sub_slice),
                         }
                     }
                 }