diff --git a/crates/compiler/src/lib.rs b/crates/compiler/src/lib.rs
index 1c1ecb13e..1a7df5e27 100644
--- a/crates/compiler/src/lib.rs
+++ b/crates/compiler/src/lib.rs
@@ -1279,6 +1279,35 @@ fn first_parse_error(
     Err(error)
 }
 
+/// The first logical input accepted by the single-input grammar.
+#[derive(Clone, Copy)]
+pub enum SingleModeStatementBoundary {
+    Simple { newline_index: usize, end: TextSize },
+    Compound { end: TextSize },
+}
+
+/// Classify a logical input without changing parser diagnostics or recovery.
+#[must_use]
+pub fn single_mode_statement_boundary(
+    parsed: &parser::Parsed<ast::Mod>,
+) -> Option<SingleModeStatementBoundary> {
+    let ast::Mod::Module(module) = parsed.syntax() else {
+        return None;
+    };
+    let first = module.body.first()?;
+    if is_compound_stmt(first) {
+        return Some(SingleModeStatementBoundary::Compound { end: first.end() });
+    }
+    let newline_index = parsed
+        .tokens()
+        .iter()
+        .position(|token| token.kind() == TokenKind::Newline)?;
+    Some(SingleModeStatementBoundary::Simple {
+        newline_index,
+        end: parsed.tokens()[newline_index].end(),
+    })
+}
+
 /// Single mode reads only the first statement when it is a simple statement, so any code after
 /// its line is reported as multiple statements, ahead of errors the rest of the source has.
 #[must_use]
@@ -1289,8 +1318,8 @@ pub fn single_mode_multiple_statements_error(
     let ast::Mod::Module(module) = parsed.syntax() else {
         return None;
     };
-    let first = module.body.first()?;
-    if is_compound_stmt(first) {
+    let boundary = single_mode_statement_boundary(parsed)?;
+    if matches!(boundary, SingleModeStatementBoundary::Compound { .. }) {
         // The interactive grammar ends a compound statement with a NEWLINE,
         // so the first token of a following statement is invalid syntax.
         let next = module.body.get(1)?;
@@ -1315,9 +1344,9 @@ pub fn single_mode_multiple_statements_error(
         ));
     }
     let tokens = parsed.tokens();
-    let newline_index = tokens
-        .iter()
-        .position(|token| token.kind() == TokenKind::Newline)?;
+    let SingleModeStatementBoundary::Simple { newline_index, .. } = boundary else {
+        unreachable!()
+    };
     let newline = &tokens[newline_index];
     if parsed
         .errors()
diff --git a/crates/vm/src/vm/compile.rs b/crates/vm/src/vm/compile.rs
index baddaddd8..061ec47e7 100644
--- a/crates/vm/src/vm/compile.rs
+++ b/crates/vm/src/vm/compile.rs
@@ -1738,6 +1738,7 @@ mod escape_warnings {
         warnings: Vec<ParserWarning>,
         tokenizer_recovery: bool,
         has_valid_syntax: bool,
+        single_boundary: Option<compiler::SingleModeStatementBoundary>,
     }
 
     fn collect_parser_warnings(
@@ -1745,9 +1746,11 @@ mod escape_warnings {
         filename: &str,
         mode: Option<ruff_python_parser::Mode>,
         inherited_barry_as_flufl: bool,
+        single_mode: bool,
     ) -> CollectedParserWarnings {
         let mut ast_tokenizer_recovery = true;
         let mut has_valid_syntax = false;
+        let mut single_boundary = None;
         let mut warnings = Vec::new();
         collect_numeric_literal_warnings(source, &mut warnings);
         // The compile that follows rejects this source; parsing it here
@@ -1765,6 +1768,9 @@ mod escape_warnings {
             let parsed = ruff_python_parser::parse_unchecked(barry_source.source(), options);
             if parsed.has_valid_syntax() {
                 has_valid_syntax = true;
+                if single_mode {
+                    single_boundary = compiler::single_mode_statement_boundary(&parsed);
+                }
                 let mut visitor = EscapeWarningVisitor {
                     source,
                     warnings: &mut warnings,
@@ -1837,6 +1843,7 @@ mod escape_warnings {
             warnings,
             tokenizer_recovery: ast_tokenizer_recovery,
             has_valid_syntax,
+            single_boundary,
         }
     }
 
@@ -1861,14 +1868,20 @@ mod escape_warnings {
             inherited_barry_as_flufl: bool,
             emitted_escapes: &[usize],
         ) -> Result<(), CompileWarningError> {
+            let is_single = matches!(mode, compiler::Mode::Single);
             let mode = match mode {
                 compiler::Mode::Eval => ruff_python_parser::Mode::Expression,
                 compiler::Mode::Exec | compiler::Mode::Single | compiler::Mode::BlockExpr => {
                     ruff_python_parser::Mode::Module
                 }
             };
-            let collected =
-                collect_parser_warnings(source, filename, Some(mode), inherited_barry_as_flufl);
+            let collected = collect_parser_warnings(
+                source,
+                filename,
+                Some(mode),
+                inherited_barry_as_flufl,
+                is_single,
+            );
             if !collected.has_valid_syntax || !collected.tokenizer_recovery {
                 // Invalid source and interpolated tokenizer warnings need a
                 // separate recovery contract. Preserve their existing behavior.
@@ -1880,9 +1893,10 @@ mod escape_warnings {
                 filename,
                 module,
                 collected.warnings,
+                collected.single_boundary,
                 WarningEmission::Standard {
                     emitted_escapes,
-                    tokenizer_recovery: collected.tokenizer_recovery,
+                    tokenizer_recovery: true,
                 },
             )
             .map(|_| ())
@@ -1902,6 +1916,7 @@ mod escape_warnings {
                 filename,
                 module,
                 warnings,
+                None,
                 WarningEmission::Standard {
                     emitted_escapes: &[],
                     tokenizer_recovery: false,
@@ -1954,6 +1969,7 @@ mod escape_warnings {
                 filename,
                 module,
                 warnings,
+                None,
                 WarningEmission::Standard {
                     emitted_escapes,
                     tokenizer_recovery: false,
@@ -1975,13 +1991,26 @@ mod escape_warnings {
                 CompileStart::Eval => Some(ruff_python_parser::Mode::Expression),
                 CompileStart::FuncType => None,
             };
-            let collected =
-                collect_parser_warnings(source, filename, mode, inherited_barry_as_flufl);
+            let collected = collect_parser_warnings(
+                source,
+                filename,
+                mode,
+                inherited_barry_as_flufl,
+                matches!(start, CompileStart::Single),
+            );
             self.emit_parser_warning_batch(
                 source,
                 filename,
                 module.map(AsObject::as_object),
                 collected.warnings,
+                if matches!(start, CompileStart::Single)
+                    && collected.has_valid_syntax
+                    && collected.tokenizer_recovery
+                {
+                    collected.single_boundary
+                } else {
+                    None
+                },
                 WarningEmission::Ast {
                     // Unlike an interactive prompt, Single compile input recovers
                     // after a parser warning becomes an error. Later numeric
@@ -2010,12 +2039,14 @@ mod escape_warnings {
                 filename,
                 Some(ruff_python_parser::Mode::Module),
                 inherited_barry_as_flufl,
+                false,
             );
             self.emit_parser_warning_batch(
                 source,
                 filename,
                 module.map(AsObject::as_object),
                 collected.warnings,
+                None,
                 WarningEmission::Interactive(emitted),
             )
             .map(|_| ())
@@ -2027,6 +2058,7 @@ mod escape_warnings {
             filename: &str,
             module: Option<&PyObject>,
             warnings: Vec<ParserWarning>,
+            single_boundary: Option<compiler::SingleModeStatementBoundary>,
             emission: WarningEmission<'_>,
         ) -> Result<Vec<usize>, CompileWarningError> {
             let (emitted_escapes, ast_tokenizer_recovery, mut interactive) = match emission {
@@ -2040,6 +2072,26 @@ mod escape_warnings {
             let mut considered_escapes = Vec::new();
             let mut parser_error = None;
             for warning in warnings {
+                // A successful single input does not parse later statements.
+                // Keep those numeric events for recovery after an earlier
+                // parser warning escalates, rather than truncating the source.
+                if parser_error.is_none()
+                    && let Some(boundary) = single_boundary
+                {
+                    let end = match (boundary, &warning) {
+                        (compiler::SingleModeStatementBoundary::Simple { end, .. }, _) => Some(end),
+                        (
+                            compiler::SingleModeStatementBoundary::Compound { end },
+                            ParserWarning::Escape(_, EscapeOrigin::Parser, _),
+                        ) => Some(end),
+                        // Compound input requests another token and can emit
+                        // tokenizer warnings while rejecting the next statement.
+                        _ => None,
+                    };
+                    if end.is_some_and(|end| warning.offset() >= end.to_usize()) {
+                        continue;
+                    }
+                }
                 // CPython resumes tokenization after a parser-origin SyntaxError.
                 // Preserve ordinary warning order and never replay prior warnings.
                 if parser_error.is_some() && !matches!(warning, ParserWarning::Numeric { .. }) {