diff --git a/crates/oxc_prettier/src/printer/mod.rs b/crates/oxc_prettier/src/printer/mod.rs
index a285dbb4d..cf34c8824 100644
--- a/crates/oxc_prettier/src/printer/mod.rs
+++ b/crates/oxc_prettier/src/printer/mod.rs
@@ -5,7 +5,7 @@
 
 mod command;
 
-use std::collections::VecDeque;
+use std::{collections::VecDeque, vec};
 
 use crate::{
     doc::{Doc, Group},
@@ -97,14 +97,8 @@ impl<'a> Printer<'a> {
                 #[allow(clippy::cast_possible_wrap)]
                 let remaining_width = (self.options.print_width as isize) - (self.pos as isize);
 
-                if !group.should_break && self.fits(&group.contents, indent, remaining_width) {
-                    self.cmds.extend(
-                        group
-                            .contents
-                            .into_iter()
-                            .rev()
-                            .map(|doc| Command::new(indent, Mode::Flat, doc)),
-                    );
+                if !group.should_break && self.fits(&group.contents, remaining_width) {
+                    self.cmds.push(Command::new(indent, Mode::Flat, Doc::Group(group)));
                 } else {
                     self.cmds.extend(
                         group
@@ -166,51 +160,61 @@ impl<'a> Printer<'a> {
     }
 
     #[allow(clippy::cast_possible_wrap)]
-    fn fits(
-        &self,
-        doc: &oxc_allocator::Vec<'a, Doc<'a>>,
-        indent: Indent,
-        remaining_width: isize,
-    ) -> bool {
+    fn fits(&self, docs: &oxc_allocator::Vec<'a, Doc<'a>>, remaining_width: isize) -> bool {
         let mut remaining_width = remaining_width;
 
         // TODO: these should be commands
-        let mut queue: VecDeque<&Doc<'a>> = doc.iter().collect();
+        let mut queue: VecDeque<(Mode, &Doc)> = docs.iter().map(|doc| (Mode::Flat, doc)).collect();
+        let mut cmds = self.cmds.iter().rev();
 
-        while let Some(next) = queue.pop_front() {
-            match next {
+        while let Some((mode, doc)) = queue.pop_front() {
+            let is_break = matches!(mode, Mode::Break);
+            match doc {
                 Doc::Str(string) => {
                     remaining_width -= string.len() as isize;
                 }
-                Doc::IndentIfBreak(docs) | Doc::Array(docs) | Doc::Indent(docs) => {
+                Doc::IndentIfBreak(docs) | Doc::Indent(docs) | Doc::Array(docs) => {
                     // Prepend docs to the queue
                     for d in docs.iter().rev() {
-                        queue.push_front(d);
-                    }
-
-                    if matches!(next, Doc::Indent(_)) {
-                        remaining_width -= (self.options.tab_width * indent.length) as isize;
+                        queue.push_front((mode, d));
                     }
                 }
                 Doc::Group(group) => {
-                    if group.should_break {
-                        return false;
-                    }
+                    let mode = if group.should_break { Mode::Break } else { mode };
                     for d in group.contents.iter().rev() {
-                        queue.push_front(d);
+                        queue.push_front((mode, d));
+                    }
+                }
+                Doc::IfBreak(doc) => {
+                    if is_break {
+                        queue.push_front((mode, doc));
+                    }
+                }
+                Doc::Line => {
+                    if is_break {
+                        return true;
+                    }
+                    remaining_width -= 1_isize;
+                }
+                Doc::Softline => {
+                    if is_break {
+                        return true;
                     }
                 }
-                // trying to fit on a single line, so we don't need to consider line breaks
-                Doc::IfBreak { .. } | Doc::Softline => {}
-                Doc::Line => remaining_width -= 1,
                 Doc::Hardline => {
-                    return false;
+                    return true;
                 }
             }
 
             if remaining_width < 0 {
                 return false;
             }
+
+            if queue.is_empty() {
+                if let Some(cmd) = cmds.next() {
+                    queue.push_back((cmd.mode, &cmd.doc));
+                }
+            }
         }
 
         true
diff --git a/tasks/prettier_conformance/prettier.snap.md b/tasks/prettier_conformance/prettier.snap.md
index ba841326a..a9be5a2da 100644
--- a/tasks/prettier_conformance/prettier.snap.md
+++ b/tasks/prettier_conformance/prettier.snap.md
@@ -1,4 +1,4 @@
-Compatibility: 114/601 (18.97%)
+Compatibility: 113/601 (18.80%)
 
 # Failed
 
@@ -89,6 +89,7 @@ Compatibility: 114/601 (18.97%)
 
 ### async
 * async/async-iteration.js
+* async/async-shorthand-method.js
 * async/await-parse.js
 * async/conditional-expression.js
 * async/exponentiation.js
@@ -131,8 +132,8 @@ Compatibility: 114/601 (18.97%)
 
 ### call/first-argument-expansion
 * call/first-argument-expansion/expression-2nd-arg.js
+* call/first-argument-expansion/issue-12892.js
 * call/first-argument-expansion/issue-13237.js
-* call/first-argument-expansion/issue-14454.js
 * call/first-argument-expansion/issue-2456.js
 * call/first-argument-expansion/issue-4401.js
 * call/first-argument-expansion/issue-5172.js
@@ -407,7 +408,6 @@ Compatibility: 114/601 (18.97%)
 
 ### import
 * import/comments.js
-* import/inline.js
 * import/same-local-and-imported.js
 
 ### label
@@ -499,8 +499,12 @@ Compatibility: 114/601 (18.97%)
 ### nullish-coalescing
 * nullish-coalescing/nullish_coalesing_operator.js
 
+### object-colon-bug
+* object-colon-bug/bug.js
+
 ### object-prop-break-in
 * object-prop-break-in/comment.js
+* object-prop-break-in/long-value.js
 * object-prop-break-in/short-keys.js
 * object-prop-break-in/test.js
 
@@ -515,6 +519,7 @@ Compatibility: 114/601 (18.97%)
 * objects/escape-sequence-key.js
 * objects/expand.js
 * objects/expression.js
+* objects/getter-setter.js
 * objects/range.js
 * objects/right-break.js
 
@@ -612,10 +617,6 @@ Compatibility: 114/601 (18.97%)
 * switch/empty_switch.js
 * switch/switch.js
 
-### tab-width
-* tab-width/class.js
-* tab-width/nested-functions.spec.js
-
 ### template
 * template/arrow.js
 * template/call.js