diff --git a/common.gypi b/common.gypi
index 2967d1e63a48..e208978fabbf 100644
--- a/common.gypi
+++ b/common.gypi
@@ -44,7 +44,7 @@
 
     # Reset this number to 0 on major V8 upgrades.
     # Increment by one for each non-official patch applied to deps/v8.
-    'v8_embedder_string': '-node.40',
+    'v8_embedder_string': '-node.45',
 
     ##### V8 defaults for Node.js #####
 
diff --git a/deps/v8/src/regexp/regexp-compiler.cc b/deps/v8/src/regexp/regexp-compiler.cc
index a3e7c170d430..ba1452be9fca 100644
--- a/deps/v8/src/regexp/regexp-compiler.cc
+++ b/deps/v8/src/regexp/regexp-compiler.cc
@@ -346,7 +346,7 @@ RegExpCompiler::CompilationResult RegExpCompiler::Assemble(
     return CompilationResult::RegExpTooBig();
   };
 
-  ZoneVector<RegExpNode*> work_list(zone());
+  ZoneVector<WorkItem> work_list(zone());
   work_list_ = &work_list;
   Label fail;
   macro_assembler_->PushBacktrack(&fail);
@@ -357,11 +357,13 @@ RegExpCompiler::CompilationResult RegExpCompiler::Assemble(
   macro_assembler_->BindJumpTarget(&fail);
   macro_assembler_->Fail();
   while (!work_list.empty()) {
-    RegExpNode* node = work_list.back();
+    WorkItem item = work_list.back();
+    RegExpNode* node = item.node;
     TRACE_WITH_NODE(this, "Popping from worklist ", node);
     work_list.pop_back();
     node->set_on_work_list(false);
     if (!node->label()->is_bound()) {
+      set_flags(item.flags);
       if (node->Emit(this, &new_trace).IsError()) {
         return ReportError();
       }
@@ -2132,6 +2134,7 @@ EmitResult AssertionNode::EmitBoundaryCheck(RegExpCompiler* compiler,
   }
   bool at_boundary = (assertion_type_ == AssertionNode::AT_BOUNDARY);
   if (next_is_word_character == Trace::UNKNOWN) {
+    const RegExpFlags flags = compiler->flags();
     Label before_non_word;
     Label before_word;
     if (trace->characters_preloaded() != 1) {
@@ -2146,6 +2149,7 @@ EmitResult AssertionNode::EmitBoundaryCheck(RegExpCompiler* compiler,
                                         at_boundary ? kIsNonWord : kIsWord));
     assembler->GoTo(&ok);
 
+    compiler->set_flags(flags);
     assembler->Bind(&before_word);
     RETURN_IF_ERROR(BacktrackIfPrevious(compiler, trace,
                                         at_boundary ? kIsWord : kIsNonWord));
@@ -3841,8 +3845,13 @@ class Analysis : public NodeVisitor {
   }
 
   void VisitChoice(ChoiceNode* that) override {
+    // Flags need to be reset to the state of the ChoiceNode at the beginning
+    // of each alternative, as flags might be modified when visiting an
+    // alternative.
+    RegExpFlags header_flags = flags();
     for (int i = 0; i < that->alternatives()->length(); i++) {
       EnsureAnalyzed(that->alternatives()->at(i).node());
+      set_flags(header_flags);
       if (has_failed()) return;
       STATIC_FOR_EACH(Propagators::VisitChoice(that, i));
     }
@@ -3880,11 +3889,13 @@ class Analysis : public NodeVisitor {
       NegativeLookaroundChoiceNode* that) override {
     DCHECK_EQ(that->alternatives()->length(), 2);  // Lookaround and continue.
 
+    RegExpFlags header_flags = flags();
     EnsureAnalyzed(that->lookaround_node());
     if (has_failed()) return;
     STATIC_FOR_EACH(
         Propagators::VisitNegativeLookaroundChoiceLookaroundNode(that));
 
+    set_flags(header_flags);
     EnsureAnalyzed(that->continue_node());
     if (has_failed()) return;
     STATIC_FOR_EACH(
diff --git a/deps/v8/src/regexp/regexp-compiler.h b/deps/v8/src/regexp/regexp-compiler.h
index 6e5a8dcb66e2..d90bf720da0d 100644
--- a/deps/v8/src/regexp/regexp-compiler.h
+++ b/deps/v8/src/regexp/regexp-compiler.h
@@ -570,10 +570,15 @@ class RegExpCompiler {
   // lead surrogate and start matching from there.
   RegExpNode* OptionallyStepBackToLeadSurrogate(RegExpNode* on_success);
 
+  struct WorkItem {
+    RegExpNode* node;
+    RegExpFlags flags;
+  };
+
   inline void AddWork(RegExpNode* node) {
     if (!node->on_work_list() && !node->label()->is_bound()) {
       node->set_on_work_list(true);
-      work_list_->push_back(node);
+      work_list_->push_back({node, flags()});
     }
   }
 
@@ -644,7 +649,7 @@ class RegExpCompiler {
   int next_register_;
   int unicode_lookaround_stack_register_;
   int unicode_lookaround_position_register_;
-  ZoneVector<RegExpNode*>* work_list_;
+  ZoneVector<WorkItem>* work_list_;
   int recursion_depth_;
   RegExpFlags flags_;
   RegExpMacroAssembler* macro_assembler_;
diff --git a/deps/v8/src/regexp/regexp-parser.cc b/deps/v8/src/regexp/regexp-parser.cc
index 2792cd0f1e91..0c9bbad8497d 100644
--- a/deps/v8/src/regexp/regexp-parser.cc
+++ b/deps/v8/src/regexp/regexp-parser.cc
@@ -988,6 +988,7 @@ RegExpTree* RegExpParserImpl<CharT>::ParseDisjunction() {
         // Restore previous state.
         state = state->previous_state();
         builder = state->builder();
+        flags_ = builder->flags();
 
         builder->AddAtom(body);
         // For compatibility with JSC and ES3, we allow quantifiers after
diff --git a/deps/v8/test/mjsunit/regexp-modifiers.js b/deps/v8/test/mjsunit/regexp-modifiers.js
index e012dc8d406c..91b1f2364bdc 100644
--- a/deps/v8/test/mjsunit/regexp-modifiers.js
+++ b/deps/v8/test/mjsunit/regexp-modifiers.js
@@ -73,3 +73,40 @@ test(
     /(?m:^f(?si:.o)$)/, ['foo', '\nfoO', 'f\no\n', '\nf\rO\n'],
     ['Foo', 'F\no\n']);
 test(/(?i:.oo)/, ['Foo', 'FOO', 'fOo', 'foO']);
+
+test(/(?i:foo)[x-z]/v, ['Foox', 'fOoz'], ['fooX','FooZ']);
+
+// Nodes inside a modifier group deferred to the work list must be compiled with
+// the group's inner flags, not the outer flags.
+test(
+    /^(?i:(?:a|b)(?:c|d)(?:e|f)(?:g|h)(?:i|j)(?:k|l)(?:m|n)X)/,
+    ['acegikmx', 'acegikmX', 'bdfhjlnx', 'bdfhjlnX'],
+    ['acegikmy', 'bdfhjlny']);
+
+// Symmetrically, nodes inside a (?-i:...) group under outer /i must compile
+// case-sensitively even when deferred.
+test(
+    /^(?-i:(?:a|b)(?:c|d)(?:e|f)(?:g|h)(?:i|j)(?:k|l)(?:m|n)x)/i,
+    ['acegikmx', 'bdfhjlnx'],
+    ['acegikmX', 'bdfhjlnX']);
+
+// Boundary assertions inside modifier groups with alternations must not leak
+// flags between branches during code generation.
+test(/(?i:\.|\bNULL)/, ['null', 'NULL', 'Null', '.foo'], ['xyz']);
+test(/(?i:\bNULL|\.)/, ['null', 'NULL', '.foo'], ['xyz']);
+test(/(?i:\.|\BNULL)/, ['xnull', 'xNULL'], ['null', 'xyz']);
+test(/(?i:\W|\bNULL)/, ['null', 'NULL', '!'], ['x']);
+test(/(?i:!|\?|\bNULL)/, ['null', 'NULL', '!', '?'], ['x']);
+test(/(?i:\.|\bnUll)/, ['null', 'NULL']);
+test(/(?i:\.|\bnuLl)/, ['null', 'NULL']);
+test(/(?i:\.|\bnulL)/, ['null', 'NULL']);
+test(/(?-i:(?i:\.|\bNULL))/, ['null', 'NULL', '.foo'], ['xyz']);
+test(/(?i:(?-i:\.|\bNULL))/, ['NULL', '.foo'], ['null', 'xyz']);
+
+// A modifier group inside a negative lookaround must not leak its flags into
+// the continuation. Analysis visits the two branches of the lookaround choice
+// in sequence, so without a reset the continuation's classes are made case
+// independent under the group's flags rather than the pattern's.
+test(/(?!(?i:x|y))[K]/, ['K'], ['k']);
+test(/(?<!(?i:x|y))[K]/, ['K'], ['k']);
+test(/(?!(?-i:x|y))[K]/i, ['K', 'k']);
diff --git a/deps/v8/test/mjsunit/regress/regress-510487690.js b/deps/v8/test/mjsunit/regress/regress-510487690.js
new file mode 100644
index 000000000000..856fb25b272d
--- /dev/null
+++ b/deps/v8/test/mjsunit/regress/regress-510487690.js
@@ -0,0 +1,5 @@
+// Copyright 2026 the V8 project authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+assertTrue(/(?i:x|[a-f])/.test("F"));