diff --git a/moli-benchmark/wpt-cross-current/passed-cases.txt b/moli-benchmark/wpt-cross-current/passed-cases.txt
index cd82e2ac6b..7a3ceb06a6 100644
--- a/moli-benchmark/wpt-cross-current/passed-cases.txt
+++ b/moli-benchmark/wpt-cross-current/passed-cases.txt
@@ -7586,6 +7586,7 @@ html/semantics/scripting-1/the-script-element/json-module/parse-error.html
 html/semantics/scripting-1/the-script-element/json-module/script-element-json-src.html
 html/semantics/scripting-1/the-script-element/json-module/valid-content-type.html
 html/semantics/scripting-1/the-script-element/load-error-events-1.html
+html/semantics/scripting-1/the-script-element/load-error-events-3.html
 html/semantics/scripting-1/the-script-element/microtasks/checkpoint-after-window-onerror-module.html
 html/semantics/scripting-1/the-script-element/microtasks/checkpoint-after-window-onerror.html
 html/semantics/scripting-1/the-script-element/microtasks/checkpoint-after-workerglobalscope-onerror.html
diff --git a/moli-core/tests/fixtures/runtime/document_write_stylesheet_probe.js b/moli-core/tests/fixtures/runtime/document_write_stylesheet_probe.js
new file mode 100644
index 0000000000..72546e4c9a
--- /dev/null
+++ b/moli-core/tests/fixtures/runtime/document_write_stylesheet_probe.js
@@ -0,0 +1,5 @@
+styleNestingEvents.push('script');
+window.styleNestingRan = true;
+window.styleNestingSheetAtRun = document.getElementById('gate').sheet !== null;
+window.styleNestingCurrentScript = document.currentScript.id;
+document.write('<span id="written">ok</span>');
diff --git a/moli-core/tests/scripts.rs b/moli-core/tests/scripts.rs
index 469e0cbf67..82c5b0a764 100644
--- a/moli-core/tests/scripts.rs
+++ b/moli-core/tests/scripts.rs
@@ -40,6 +40,9 @@ mod document_write_insertion;
 #[path = "scripts/document_write_errors.rs"]
 mod document_write_errors;
 
+#[path = "scripts/document_write_stylesheets.rs"]
+mod document_write_stylesheets;
+
 #[path = "scripts/parser_cleanup.rs"]
 mod parser_cleanup;
 
diff --git a/moli-core/tests/scripts/document_write_stylesheets.rs b/moli-core/tests/scripts/document_write_stylesheets.rs
new file mode 100644
index 0000000000..cd51e74278
--- /dev/null
+++ b/moli-core/tests/scripts/document_write_stylesheets.rs
@@ -0,0 +1,263 @@
+use super::*;
+
+const SCRIPT: &str = include_str!("../fixtures/runtime/document_write_stylesheet_probe.js");
+const INITIALIZE: &str = "window.styleNestingEvents = []; window.styleNestingRan = false;";
+const OBSERVE_AND_RELEASE: &str = r#"
+    window.styleNestingRanAtReturn = styleNestingRan;
+    window.styleNestingRestoredScript = document.currentScript?.id ?? null;
+    styleNestingEvents.push('after-write');
+    fetch('/assets/dynamic_blocking_stylesheet_script_executed');
+"#;
+
+fn markup_url(server: &FixtureServer, markup: &str) -> String {
+    let mut url = url::Url::parse(&server.url("/compat/child-dynamic-markup-document")).unwrap();
+    url.query_pairs_mut().append_pair("markup", markup);
+    url.into()
+}
+
+fn script_markup(id: &str, source: &str, external: bool) -> String {
+    if external {
+        let source = url::form_urlencoded::byte_serialize(source.as_bytes())
+            .collect::<String>()
+            .replace('+', "%20");
+        format!("<script id={id} src=\"data:text/javascript,{source}\"></script>")
+    } else {
+        format!("<script id={id}>{source}</script>")
+    }
+}
+
+async fn stylesheet_wait_respects_parser_script_nesting(
+    child: bool,
+    script_created: bool,
+    nested: bool,
+    external: bool,
+    outer_external: bool,
+) -> Result<()> {
+    let server = FixtureServer::spawn().await?;
+    let browser = Browser::new(AppConfig::default())?;
+    let script = script_markup("inner", SCRIPT, external);
+    let written = format!(
+        "<link id=gate rel=stylesheet href=/assets/dynamic_blocking_stylesheet_gated.css>{script}"
+    );
+    let fixture = if nested {
+        let written = serde_json::to_string(&written)?.replace('<', "\\u003c");
+        let outer = script_markup(
+            "outer",
+            &format!("{INITIALIZE}document.write({written});{OBSERVE_AND_RELEASE}"),
+            outer_external,
+        );
+        format!("<!doctype html><head>{outer}</head><body><main id=tail>tail</main>")
+    } else {
+        format!("<!doctype html><head>{written}</head><body><main id=tail>tail</main>")
+    };
+    let initial = if script_created {
+        "<!doctype html><body>"
+    } else {
+        &fixture
+    };
+    let initial = if child {
+        format!(
+            "<!doctype html><body><iframe id=target src=\"{}\"></iframe>",
+            markup_url(&server, initial)
+        )
+    } else {
+        initial.to_owned()
+    };
+    let mut page = tokio::time::timeout(
+        Duration::from_secs(10),
+        browser.fetch(&markup_url(&server, &initial)),
+    )
+    .await??;
+    let receiver = if child {
+        "document.getElementById('target').contentWindow"
+    } else {
+        "window"
+    };
+    if script_created {
+        let initialize = if nested { "" } else { INITIALIZE };
+        let observe = if nested { "" } else { OBSERVE_AND_RELEASE };
+        let expression = format!(
+            r#"new Promise(resolve => {{
+              const win = {receiver};
+              const doc = win.document;
+              doc.open();
+              win.eval({});
+              doc.addEventListener('DOMContentLoaded', () => resolve(true), {{once: true}});
+              doc.write({});
+              win.eval({});
+              doc.close();
+            }})"#,
+            serde_json::to_string(initialize)?,
+            serde_json::to_string(&fixture)?,
+            serde_json::to_string(observe)?,
+        );
+        tokio::time::timeout(
+            Duration::from_secs(10),
+            page.evaluate_runtime_expression_with_await_async(&expression, true),
+        )
+        .await??;
+    }
+    let observed = page
+        .evaluate_runtime_expression_with_await_async(
+            &format!(
+                r#"(() => {{
+                  const win = {receiver};
+                  return JSON.stringify({{
+                    events: win.styleNestingEvents,
+                    ranAtReturn: win.styleNestingRanAtReturn,
+                    sheetAtRun: win.styleNestingSheetAtRun,
+                    currentScript: win.styleNestingCurrentScript,
+                    restoredScript: win.styleNestingRestoredScript,
+                    written: win.document.getElementById('written')?.textContent,
+                    tail: win.document.getElementById('tail')?.textContent
+                  }});
+                }})()"#
+            ),
+            true,
+        )
+        .await?;
+    let observed: serde_json::Value = serde_json::from_str(
+        observed["value"]
+            .as_str()
+            .expect("stylesheet nesting observation"),
+    )?;
+    let immediate = nested && !external;
+    assert_eq!(
+        observed,
+        serde_json::json!({
+            "events": if immediate { ["script", "after-write"] } else { ["after-write", "script"] },
+            "ranAtReturn": immediate,
+            "sheetAtRun": !immediate,
+            "currentScript": "inner",
+            "restoredScript": if nested { Some("outer") } else { None },
+            "written": "ok",
+            "tail": "tail"
+        }),
+        "child={child}, script_created={script_created}, nested={nested}, external={external}, outer_external={outer_external}"
+    );
+    server.shutdown().await;
+    Ok(())
+}
+
+macro_rules! stylesheet_nesting_test {
+    ($name:ident, $child:expr, $created:expr, $nested:expr, $external:expr) => {
+        stylesheet_nesting_test!($name, $child, $created, $nested, $external, false);
+    };
+    ($name:ident, $child:expr, $created:expr, $nested:expr, $external:expr, $outer_external:expr) => {
+        #[tokio::test(flavor = "multi_thread")]
+        async fn $name() -> Result<()> {
+            stylesheet_wait_respects_parser_script_nesting(
+                $child,
+                $created,
+                $nested,
+                $external,
+                $outer_external,
+            )
+            .await
+        }
+    };
+}
+
+stylesheet_nesting_test!(
+    main_nested_inline_ignores_stylesheet_wait,
+    false,
+    false,
+    true,
+    false
+);
+stylesheet_nesting_test!(
+    child_nested_inline_ignores_stylesheet_wait,
+    true,
+    false,
+    true,
+    false
+);
+stylesheet_nesting_test!(
+    main_open_nested_inline_ignores_stylesheet_wait,
+    false,
+    true,
+    true,
+    false
+);
+stylesheet_nesting_test!(
+    child_open_nested_inline_ignores_stylesheet_wait,
+    true,
+    true,
+    true,
+    false
+);
+stylesheet_nesting_test!(
+    main_nested_external_keeps_stylesheet_wait,
+    false,
+    false,
+    true,
+    true
+);
+stylesheet_nesting_test!(
+    child_nested_external_keeps_stylesheet_wait,
+    true,
+    false,
+    true,
+    true
+);
+stylesheet_nesting_test!(
+    main_open_nested_external_keeps_stylesheet_wait,
+    false,
+    true,
+    true,
+    true
+);
+stylesheet_nesting_test!(
+    child_open_nested_external_keeps_stylesheet_wait,
+    true,
+    true,
+    true,
+    true
+);
+stylesheet_nesting_test!(
+    main_open_direct_inline_keeps_stylesheet_wait,
+    false,
+    true,
+    false,
+    false
+);
+stylesheet_nesting_test!(
+    child_open_direct_inline_keeps_stylesheet_wait,
+    true,
+    true,
+    false,
+    false
+);
+
+stylesheet_nesting_test!(
+    main_external_outer_inline_ignores_stylesheet_wait,
+    false,
+    false,
+    true,
+    false,
+    true
+);
+stylesheet_nesting_test!(
+    child_external_outer_inline_ignores_stylesheet_wait,
+    true,
+    false,
+    true,
+    false,
+    true
+);
+stylesheet_nesting_test!(
+    main_open_external_outer_inline_ignores_stylesheet_wait,
+    false,
+    true,
+    true,
+    false,
+    true
+);
+stylesheet_nesting_test!(
+    child_open_external_outer_inline_ignores_stylesheet_wait,
+    true,
+    true,
+    true,
+    false,
+    true
+);
diff --git a/moli-renderer-v8/src/document_runtime.rs b/moli-renderer-v8/src/document_runtime.rs
index 023cb67924..f7b8ad895e 100644
--- a/moli-renderer-v8/src/document_runtime.rs
+++ b/moli-renderer-v8/src/document_runtime.rs
@@ -291,6 +291,10 @@ impl ParserConnectedScriptBridge {
         self.parser_control.enter_parser_script_nesting()
     }
 
+    pub(crate) fn parser_script_nesting_level(&self) -> usize {
+        self.parser_control.parser_script_nesting_level()
+    }
+
     pub(crate) fn run_state(&self) -> DocumentParserRunState {
         self.parser_control.run_state()
     }
diff --git a/moli-renderer-v8/src/document_runtime/document_write.rs b/moli-renderer-v8/src/document_runtime/document_write.rs
index 0bd58c3fa3..a3c4eb86a1 100644
--- a/moli-renderer-v8/src/document_runtime/document_write.rs
+++ b/moli-renderer-v8/src/document_runtime/document_write.rs
@@ -2268,9 +2268,16 @@ impl DocumentRuntime {
                 blocking_signatures_before,
                 script,
             } => {
-                if self.has_pending_parser_script_blocking_stylesheet_signatures(
-                    blocking_signatures_before.iter(),
-                ) {
+                // Preparing an inline script while another parser script runs raises
+                // HTML's script nesting level above one, so it executes immediately.
+                let nested_inline =
+                    matches!(script.source, crate::planning::ScriptSource::Inline(_))
+                        && parser_bridge.parser_script_nesting_level() > 0;
+                if !nested_inline
+                    && self.has_pending_parser_script_blocking_stylesheet_signatures(
+                        blocking_signatures_before.iter(),
+                    )
+                {
                     if matches!(script.source, crate::planning::ScriptSource::External) {
                         self.start_document_write_stylesheet_blocked_external_script(
                             scope,
diff --git a/moli-renderer-v8/src/native_bridge/context_host/child_documents/live_parser.rs b/moli-renderer-v8/src/native_bridge/context_host/child_documents/live_parser.rs
index 5459b4d278..ba422d7900 100644
--- a/moli-renderer-v8/src/native_bridge/context_host/child_documents/live_parser.rs
+++ b/moli-renderer-v8/src/native_bridge/context_host/child_documents/live_parser.rs
@@ -1697,6 +1697,7 @@ impl JsContextHost {
         let ParserScriptHandoff::BlockingClassic {
             node_id,
             start_line,
+            blocking_signatures_before,
             script,
             ..
         } = handoff
@@ -1707,6 +1708,19 @@ impl JsContextHost {
             (ScriptKind::Classic, ScriptSource::Inline(source)) => source.clone(),
             _ => return false,
         };
+        // Only nested inline parser scripts bypass blocking stylesheets. A direct
+        // document.write() into a script-created parser must wait for them.
+        if !self.child_document_is_executing_parser_script(document_handle)
+            && self
+                .frame_owner_store
+                .current_child_document_owner(child_handle)
+                .is_some_and(|owner| {
+                    self.frame_document_blocking_stylesheets
+                        .blocks_signatures(owner, blocking_signatures_before.iter())
+                })
+        {
+            return false;
+        }
         let Some(mut job) = self.frame_owner_child_parser_classic_script_job(
             child_handle,
             Some(*node_id),