diff --git a/apps/oxfmt/conformance/run.ts b/apps/oxfmt/conformance/run.ts
index 969a8b5591a2f..3d5ba834ad77f 100644
--- a/apps/oxfmt/conformance/run.ts
+++ b/apps/oxfmt/conformance/run.ts
@@ -96,8 +96,6 @@ const categories: Category[] = [
         "js-in-html(`<script>`)-in-js needs lot more work; Please see oxc_formatter/src/print/template/embed/html.rs",
       "webawesome/relative-time/relative-time.test.ts":
         "html-in-js: Need to solve `label({ embed, hug }))` + `shouldExpandLastArg`",
-      "webawesome/slider/slider.ts":
-        "`@decorator` + union type: https://github.com/oxc-project/oxc/issues/20519",
     },
   },
   {
diff --git a/crates/oxc_formatter/src/formatter/printer/mod.rs b/crates/oxc_formatter/src/formatter/printer/mod.rs
index a6563cabd5da0..e236289fb23d7 100644
--- a/crates/oxc_formatter/src/formatter/printer/mod.rs
+++ b/crates/oxc_formatter/src/formatter/printer/mod.rs
@@ -1037,6 +1037,17 @@ impl<'a, 'print> FitsMeasurer<'a, 'print> {
                     // is what the mode's initialized to by default
                     // This means, the printer is outside of the current element at this point and any
                     // line break should be printed as regular line break -> Fits
+                    //
+                    // Before returning, resolve any pending space so the width check is accurate.
+                    // Without this, a deferred `Space` before a group boundary can be lost when
+                    // the fits measurer exits early via an expanded-mode line break, causing the
+                    // measured width to be off by one.
+                    if self.state.pending_space {
+                        self.state.line_width += 1;
+                        if self.state.line_width > usize::from(self.options().print_width) {
+                            return Ok(Fits::No);
+                        }
+                    }
                     return Ok(Fits::Yes);
                 }
             }
diff --git a/crates/oxc_formatter/tests/fixtures/ts/class/issue-20519.ts b/crates/oxc_formatter/tests/fixtures/ts/class/issue-20519.ts
new file mode 100644
index 0000000000000..d0fccfea59ca9
--- /dev/null
+++ b/crates/oxc_formatter/tests/fixtures/ts/class/issue-20519.ts
@@ -0,0 +1,23 @@
+// Long decorator + union type: decorator should go on its own line
+class SlSlider extends ShoelaceElement {
+  @property({ attribute: 'tooltip-placement', reflect: true }) tooltipPlacement: 'top' | 'right' |
+'bottom' | 'left' =
+    'top';
+}
+
+// Short decorator + long union type: decorator should stay inline
+class WaTooltip extends WebAwesomeElement {
+  @property() placement:
+    | "top"
+    | "top-start"
+    | "top-end"
+    | "right"
+    | "right-start"
+    | "right-end"
+    | "bottom"
+    | "bottom-start"
+    | "bottom-end"
+    | "left"
+    | "left-start"
+    | "left-end" = "bottom";
+}
diff --git a/crates/oxc_formatter/tests/fixtures/ts/class/issue-20519.ts.snap b/crates/oxc_formatter/tests/fixtures/ts/class/issue-20519.ts.snap
new file mode 100644
index 0000000000000..32f9ccbdde5e5
--- /dev/null
+++ b/crates/oxc_formatter/tests/fixtures/ts/class/issue-20519.ts.snap
@@ -0,0 +1,86 @@
+---
+source: crates/oxc_formatter/tests/fixtures/mod.rs
+assertion_line: 234
+---
+==================== Input ====================
+// Long decorator + union type: decorator should go on its own line
+class SlSlider extends ShoelaceElement {
+  @property({ attribute: 'tooltip-placement', reflect: true }) tooltipPlacement: 'top' | 'right' |
+'bottom' | 'left' =
+    'top';
+}
+
+// Short decorator + long union type: decorator should stay inline
+class WaTooltip extends WebAwesomeElement {
+  @property() placement:
+    | "top"
+    | "top-start"
+    | "top-end"
+    | "right"
+    | "right-start"
+    | "right-end"
+    | "bottom"
+    | "bottom-start"
+    | "bottom-end"
+    | "left"
+    | "left-start"
+    | "left-end" = "bottom";
+}
+
+==================== Output ====================
+------------------
+{ printWidth: 80 }
+------------------
+// Long decorator + union type: decorator should go on its own line
+class SlSlider extends ShoelaceElement {
+  @property({ attribute: "tooltip-placement", reflect: true })
+  tooltipPlacement: "top" | "right" | "bottom" | "left" = "top";
+}
+
+// Short decorator + long union type: decorator should stay inline
+class WaTooltip extends WebAwesomeElement {
+  @property() placement:
+    | "top"
+    | "top-start"
+    | "top-end"
+    | "right"
+    | "right-start"
+    | "right-end"
+    | "bottom"
+    | "bottom-start"
+    | "bottom-end"
+    | "left"
+    | "left-start"
+    | "left-end" = "bottom";
+}
+
+-------------------
+{ printWidth: 100 }
+-------------------
+// Long decorator + union type: decorator should go on its own line
+class SlSlider extends ShoelaceElement {
+  @property({ attribute: "tooltip-placement", reflect: true }) tooltipPlacement:
+    | "top"
+    | "right"
+    | "bottom"
+    | "left" = "top";
+}
+
+// Short decorator + long union type: decorator should stay inline
+class WaTooltip extends WebAwesomeElement {
+  @property() placement:
+    | "top"
+    | "top-start"
+    | "top-end"
+    | "right"
+    | "right-start"
+    | "right-end"
+    | "bottom"
+    | "bottom-start"
+    | "bottom-end"
+    | "left"
+    | "left-start"
+    | "left-end" = "bottom";
+}
+
+===================== End =====================
diff --git a/tasks/prettier_conformance/snapshots/prettier.ts.snap.md b/tasks/prettier_conformance/snapshots/prettier.ts.snap.md
index 626e18063d110..3e5bb7fde3fb7 100644
--- a/tasks/prettier_conformance/snapshots/prettier.ts.snap.md
+++ b/tasks/prettier_conformance/snapshots/prettier.ts.snap.md
@@ -6,11 +6,11 @@ ts compatibility: 591/601 (98.34%)
 | :-------- | :--------------: | :---------: |
 | typescript/arrow/comments.ts | 💥✨ | 44.44% |
 | typescript/arrow/comments/issue-11100.ts | 💥 | 84.00% |
-| typescript/as/break-after-keyword/18148.ts | 💥 | 82.22% |
 | typescript/class/empty-method-body.ts | 💥 | 80.00% |
 | typescript/comments/mapped_types.ts | 💥 | 96.77% |
 | typescript/comments/method_types.ts | 💥 | 82.05% |
 | typescript/mapped-type/issue-11098.ts | 💥 | 97.03% |
 | typescript/property-signature/consistent-with-flow/comments.ts | 💥 | 80.00% |
 | typescript/union/comments/18389.ts | 💥 | 51.28% |
+| typescript/union/consistent-with-flow/comment.ts | 💥 | 86.96% |
 | typescript/union/single-type/single-type.ts | 💥 | 66.67% |