diff --git a/VMP_TESTING_NOTES.md b/VMP_TESTING_NOTES.md
index 7623d66..f3bd4a7 100644
--- a/VMP_TESTING_NOTES.md
+++ b/VMP_TESTING_NOTES.md
@@ -65,7 +65,7 @@ Use `simple/protected381/*`.
 - These are the best local VMP-style performance targets.
 - Continue profiling semantics/memory/folder helpers there.
 - For large control-flow/semantics/inlining changes, run `python test.py vmp` from repo root. That command now fails required targets on diagnostics errors **or** `blocks_completed == 0`, while still reporting the older VMP 3.6 sample as best-effort only.
-- The current safe configuration keeps loop-header generalization disabled and relies on a higher basic-block budget for the stable 3.8.x samples.
+- The current safe configuration allows structured loop-header reuse only for reducible conditional/direct-jump headers (including short trampoline chains into a conditional header); indirect-jump and `ret` dispatcher-style loops remain blocked, and required 3.8.x samples must still validate via `python test.py vmp`.
 
 ### If the goal is older protected/VMP 3.6 support
 Use `simple/protected/simple_target_protected.vmp.exe`, but do not treat it as a normal instruction-semantics-only problem.
diff --git a/docs/REWRITE_BASELINE.md b/docs/REWRITE_BASELINE.md
index fb7e2e2..637dfb4 100644
--- a/docs/REWRITE_BASELINE.md
+++ b/docs/REWRITE_BASELINE.md
@@ -131,11 +131,11 @@ Samples without a `semantic` field are not tested. The `semantic` field is optio
 
 ### Coverage summary
 
-Current active quick-gate semantic coverage is **30 samples / 165 cases**.
+Current active quick-gate semantic coverage is **33 samples / 177 cases**.
 
 Notable current state:
-- `dummy_vm_loop` and `bytecode_vm_loop` remain active VM-shaped control-flow samples.
-- `stack_vm_loop` and `calc_sum_to_n` are currently marked `skip` because the safe VMP configuration disables loop-header generalization and these samples still exceed the block budget without it.
+- `dummy_vm_loop`, `bytecode_vm_loop`, and `stack_vm_loop` are active VM-shaped control-flow samples.
+- `calc_sum_to_n` is active again under the safe structured-loop recovery path.
 - `calc_cout` remains `ci_skip` because its C++ codegen is toolchain-dependent on CI.
 
 ## Call-boundary ABI framework
diff --git a/docs/SCOPE.md b/docs/SCOPE.md
index 8042ef2..aa76860 100644
--- a/docs/SCOPE.md
+++ b/docs/SCOPE.md
@@ -33,7 +33,7 @@ Mergen is a function-level LLVM IR lifting engine for deobfuscation and devirtua
 
 ## Quality Contract
 - Handler coverage: 112/115 handlers with oracle-backed verification
-- Active regression corpus: 30 semantic samples / 165 runtime semantic cases; `stack_vm_loop` and `calc_sum_to_n` are tracked known limitations, and `calc_cout` remains CI-skipped because its C++ codegen is toolchain-dependent
+- Active regression corpus: 33 semantic samples / 177 runtime semantic cases; structured loop recovery now keeps `calc_sum_to_n` and `stack_vm_loop` active, and `calc_cout` remains CI-skipped because its C++ codegen is toolchain-dependent
 - Determinism: golden IR hashes are enforced for tracked outputs
 - CI gates: register/flag correctness, rewrite baseline, semantic regression, and Windows build lanes
 - Targeted VMP gate: `python test.py vmp` must keep required 3.8.x targets at `blocks_completed > 0`; VMP 3.6 remains best-effort only
diff --git a/lifter/analysis/PathSolver.ipp b/lifter/analysis/PathSolver.ipp
index c7f8677..ef586e1 100644
--- a/lifter/analysis/PathSolver.ipp
+++ b/lifter/analysis/PathSolver.ipp
@@ -59,24 +59,24 @@ MERGEN_LIFTER_DEFINITION_TEMPLATES(PATH_info)::solvePath(
         visitedAddresses.contains(target) &&
         target <= blockInfo.block_address;
     auto it = addrToBB.find(target);
-    const bool generalizedHeaderLooksSimple =
-        it == addrToBB.end() || !it->second || llvm::pred_size(it->second) <= 1;
+    const bool pendingGeneralization =
+        pendingLoopGeneralizationAddresses.contains(target);
     const bool wantsGeneralization =
-        currentPathSolveAllowsLoopGeneralization() &&
-        generalizedHeaderLooksSimple &&
-        !generalizedLoopAddresses.contains(target) &&
-        backwardVisitedTarget;
+        pendingGeneralization ||
+        (backwardVisitedTarget && canGeneralizeStructuredLoopHeader(target));
     if (wantsGeneralization) {
       if (currentPathSolveContext == PathSolveContext::DirectJump) {
         stackBypassGeneralizedLoopAddresses.insert(target);
       }
       const bool generalizedBackup =
           stackBypassGeneralizedLoopAddresses.contains(target);
-      if (pendingLoopGeneralizationAddresses.contains(target) &&
-          it != addrToBB.end() && it->second && it->second->empty()) {
+      if (pendingGeneralization && it != addrToBB.end() && it->second &&
+          it->second->empty()) {
         return {it->second, false, generalizedBackup};
       }
-      pendingLoopGeneralizationAddresses.insert(target);
+      if (!pendingGeneralization) {
+        pendingLoopGeneralizationAddresses.insert(target);
+      }
       if (it != addrToBB.end() && it->second && !it->second->empty()) {
         return {replaceWithGeneralizedLoopBlock(target, name), false,
                 generalizedBackup};
diff --git a/lifter/core/LifterClass.hpp b/lifter/core/LifterClass.hpp
index 4181f92..c05aa0a 100644
--- a/lifter/core/LifterClass.hpp
+++ b/lifter/core/LifterClass.hpp
@@ -503,11 +503,49 @@ public:
   bool currentBlockUsesGeneralizedLoopState() const {
     return currentBlockRestoreMode == BlockRestoreMode::GeneralizedLoop;
   }
-  bool currentPathSolveAllowsLoopGeneralization() const {
-    // Disabled until the generalized loop heuristics can preserve real VMP exit
-    // paths without collapsing required 3.8.x targets into non-terminating IR.
+  bool currentPathSolveAllowsStructuredLoopGeneralization() const {
+    return currentPathSolveContext == PathSolveContext::ConditionalBranch ||
+           currentPathSolveContext == PathSolveContext::DirectJump;
+  }
+  bool isStructuredLoopHeaderShape(BasicBlock* block) const {
+    std::set<BasicBlock*> seenBlocks;
+    auto* current = block;
+    for (unsigned depth = 0; current && depth < 8; ++depth) {
+      if (!seenBlocks.insert(current).second || current->empty()) {
+        return false;
+      }
+      const size_t maxPreds = depth == 0 ? 2 : 1;
+      if (llvm::pred_size(current) > maxPreds) {
+        return false;
+      }
+      auto* branch = llvm::dyn_cast<llvm::BranchInst>(current->getTerminator());
+      if (!branch) {
+        return false;
+      }
+      if (branch->isConditional()) {
+        return true;
+      }
+      if (branch->getNumSuccessors() != 1) {
+        return false;
+      }
+      current = branch->getSuccessor(0);
+    }
     return false;
   }
+  bool canGeneralizeStructuredLoopHeader(uint64_t addr) {
+    if (getControlFlow() != ControlFlow::Unflatten ||
+        !currentPathSolveAllowsStructuredLoopGeneralization() ||
+        addr > blockInfo.block_address || !visitedAddresses.contains(addr) ||
+        pendingLoopGeneralizationAddresses.contains(addr) ||
+        generalizedLoopAddresses.contains(addr)) {
+      return false;
+    }
+    auto it = addrToBB.find(addr);
+    if (it == addrToBB.end() || !it->second || it->second->empty()) {
+      return false;
+    }
+    return isStructuredLoopHeaderShape(it->second);
+  }
 
   void liftBasicBlockFromAddress(uint64_t addr) {
     ++liftStats.blocks_attempted;
@@ -757,7 +795,7 @@ public:
 
   BasicBlock* getLiftedBackedgeBB(uint64_t addr) {
     if (getControlFlow() != ControlFlow::Unflatten ||
-        !currentPathSolveAllowsLoopGeneralization()) {
+        !currentPathSolveAllowsStructuredLoopGeneralization()) {
       return nullptr;
     }
     if (addr > blockInfo.block_address ||
diff --git a/lifter/test/Tester.hpp b/lifter/test/Tester.hpp
index 1b4c79e..4516265 100644
--- a/lifter/test/Tester.hpp
+++ b/lifter/test/Tester.hpp
@@ -412,11 +412,24 @@ private:
   }
 
 
-  bool runLoopGeneralizationDirectJumpBlocked(std::string& details) {
+  bool runLoopGeneralizationConditionalBranchAllowed(std::string& details) {
+    LifterUnderTest lifter;
+    lifter.currentPathSolveContext =
+        LifterUnderTest::PathSolveContext::ConditionalBranch;
+    if (!lifter.currentPathSolveAllowsStructuredLoopGeneralization()) {
+      details =
+          "  conditional-branch loop context should allow structured loop-header reuse\n";
+      return false;
+    }
+    return true;
+  }
+
+  bool runLoopGeneralizationDirectJumpAllowed(std::string& details) {
     LifterUnderTest lifter;
     lifter.currentPathSolveContext = LifterUnderTest::PathSolveContext::DirectJump;
-    if (lifter.currentPathSolveAllowsLoopGeneralization()) {
-      details = "  direct-jump loop context must stay disabled until VMP-safe generalization exists\n";
+    if (!lifter.currentPathSolveAllowsStructuredLoopGeneralization()) {
+      details =
+          "  direct-jump latch context should allow structured loop-header reuse\n";
       return false;
     }
     return true;
@@ -424,9 +437,170 @@ private:
 
   bool runLoopGeneralizationIndirectJumpBlocked(std::string& details) {
     LifterUnderTest lifter;
-    lifter.currentPathSolveContext = LifterUnderTest::PathSolveContext::IndirectJump;
-    if (lifter.currentPathSolveAllowsLoopGeneralization()) {
-      details = "  indirect-jump dispatcher context must not generalize loop state\n";
+    lifter.currentPathSolveContext =
+        LifterUnderTest::PathSolveContext::IndirectJump;
+    if (lifter.currentPathSolveAllowsStructuredLoopGeneralization()) {
+      details =
+          "  indirect-jump dispatcher context must not generalize loop state\n";
+      return false;
+    }
+    return true;
+  }
+
+  bool runLoopGeneralizationRetBlocked(std::string& details) {
+    LifterUnderTest lifter;
+    lifter.currentPathSolveContext = LifterUnderTest::PathSolveContext::Ret;
+    if (lifter.currentPathSolveAllowsStructuredLoopGeneralization()) {
+      details = "  return-path loop context must not generalize loop state\n";
+      return false;
+    }
+    return true;
+  }
+
+  bool runStructuredLoopHeaderAllowsConditionalBackedge(std::string& details) {
+    LifterUnderTest lifter;
+    lifter.currentPathSolveContext =
+        LifterUnderTest::PathSolveContext::ConditionalBranch;
+
+    auto* current = llvm::BasicBlock::Create(lifter.context, "current", lifter.fnc);
+    auto* header = llvm::BasicBlock::Create(lifter.context, "loop_header", lifter.fnc);
+    auto* body = llvm::BasicBlock::Create(lifter.context, "loop_body", lifter.fnc);
+    auto* exit = llvm::BasicBlock::Create(lifter.context, "loop_exit", lifter.fnc);
+
+    llvm::IRBuilder<> currentBuilder(current);
+    currentBuilder.CreateBr(header);
+
+    llvm::IRBuilder<> headerBuilder(header);
+    headerBuilder.CreateCondBr(llvm::ConstantInt::getTrue(lifter.context), body, exit);
+
+    llvm::IRBuilder<> bodyBuilder(body);
+    bodyBuilder.CreateRet(llvm::ConstantInt::get(llvm::Type::getInt64Ty(lifter.context), 0));
+
+    llvm::IRBuilder<> exitBuilder(exit);
+    exitBuilder.CreateRet(llvm::ConstantInt::get(llvm::Type::getInt64Ty(lifter.context), 1));
+
+    lifter.blockInfo = BBInfo(0x2000, current);
+    lifter.visitedAddresses.insert(0x1000);
+    lifter.addrToBB[0x1000] = header;
+
+    if (!lifter.canGeneralizeStructuredLoopHeader(0x1000)) {
+      details = "  visited conditional loop header should be eligible for structured reuse\n";
+      return false;
+    }
+    return true;
+  }
+
+  bool runStructuredLoopHeaderAllowsJumpChain(std::string& details) {
+    LifterUnderTest lifter;
+    lifter.currentPathSolveContext =
+        LifterUnderTest::PathSolveContext::DirectJump;
+
+    auto* current = llvm::BasicBlock::Create(lifter.context, "current", lifter.fnc);
+    auto* trampoline =
+        llvm::BasicBlock::Create(lifter.context, "loop_trampoline", lifter.fnc);
+    auto* header = llvm::BasicBlock::Create(lifter.context, "loop_header", lifter.fnc);
+    auto* body = llvm::BasicBlock::Create(lifter.context, "loop_body", lifter.fnc);
+    auto* exit = llvm::BasicBlock::Create(lifter.context, "loop_exit", lifter.fnc);
+
+    llvm::IRBuilder<> currentBuilder(current);
+    currentBuilder.CreateBr(trampoline);
+
+    llvm::IRBuilder<> trampolineBuilder(trampoline);
+    trampolineBuilder.CreateBr(header);
+
+    llvm::IRBuilder<> headerBuilder(header);
+    headerBuilder.CreateCondBr(llvm::ConstantInt::getTrue(lifter.context), body, exit);
+
+    llvm::IRBuilder<> bodyBuilder(body);
+    bodyBuilder.CreateRet(
+        llvm::ConstantInt::get(llvm::Type::getInt64Ty(lifter.context), 0));
+
+    llvm::IRBuilder<> exitBuilder(exit);
+    exitBuilder.CreateRet(
+        llvm::ConstantInt::get(llvm::Type::getInt64Ty(lifter.context), 1));
+
+    lifter.blockInfo = BBInfo(0x2000, current);
+    lifter.visitedAddresses.insert(0x1000);
+    lifter.addrToBB[0x1000] = trampoline;
+
+    if (!lifter.canGeneralizeStructuredLoopHeader(0x1000)) {
+      details =
+          "  direct-jump trampoline chain into a conditional header should be eligible for structured reuse\n";
+      return false;
+    }
+    return true;
+  }
+
+
+  bool runStructuredLoopHeaderRejectsNonConditionalTerminator(
+      std::string& details) {
+    LifterUnderTest lifter;
+    lifter.currentPathSolveContext =
+        LifterUnderTest::PathSolveContext::ConditionalBranch;
+
+    auto* current = llvm::BasicBlock::Create(lifter.context, "current", lifter.fnc);
+    auto* header = llvm::BasicBlock::Create(lifter.context, "loop_header", lifter.fnc);
+    auto* exit = llvm::BasicBlock::Create(lifter.context, "loop_exit", lifter.fnc);
+
+    llvm::IRBuilder<> currentBuilder(current);
+    currentBuilder.CreateBr(header);
+
+    llvm::IRBuilder<> headerBuilder(header);
+    headerBuilder.CreateBr(exit);
+
+    llvm::IRBuilder<> exitBuilder(exit);
+    exitBuilder.CreateRet(llvm::ConstantInt::get(llvm::Type::getInt64Ty(lifter.context), 0));
+
+    lifter.blockInfo = BBInfo(0x2000, current);
+    lifter.visitedAddresses.insert(0x1000);
+    lifter.addrToBB[0x1000] = header;
+
+    if (lifter.canGeneralizeStructuredLoopHeader(0x1000)) {
+      details = "  non-conditional header must not be treated as a structured loop header\n";
+      return false;
+    }
+    return true;
+  }
+
+  bool runStructuredLoopHeaderRejectsMultiplePredecessors(std::string& details) {
+    LifterUnderTest lifter;
+    lifter.currentPathSolveContext =
+        LifterUnderTest::PathSolveContext::ConditionalBranch;
+
+    auto* current = llvm::BasicBlock::Create(lifter.context, "current", lifter.fnc);
+    auto* alternate = llvm::BasicBlock::Create(lifter.context, "alternate", lifter.fnc);
+    auto* third = llvm::BasicBlock::Create(lifter.context, "third", lifter.fnc);
+    auto* header = llvm::BasicBlock::Create(lifter.context, "loop_header", lifter.fnc);
+    auto* body = llvm::BasicBlock::Create(lifter.context, "loop_body", lifter.fnc);
+    auto* exit = llvm::BasicBlock::Create(lifter.context, "loop_exit", lifter.fnc);
+
+    llvm::IRBuilder<> currentBuilder(current);
+    currentBuilder.CreateBr(header);
+
+    llvm::IRBuilder<> alternateBuilder(alternate);
+    alternateBuilder.CreateBr(header);
+
+    llvm::IRBuilder<> thirdBuilder(third);
+    thirdBuilder.CreateBr(header);
+
+    llvm::IRBuilder<> headerBuilder(header);
+    headerBuilder.CreateCondBr(llvm::ConstantInt::getTrue(lifter.context), body, exit);
+
+    llvm::IRBuilder<> bodyBuilder(body);
+    bodyBuilder.CreateRet(
+        llvm::ConstantInt::get(llvm::Type::getInt64Ty(lifter.context), 0));
+
+    llvm::IRBuilder<> exitBuilder(exit);
+    exitBuilder.CreateRet(
+        llvm::ConstantInt::get(llvm::Type::getInt64Ty(lifter.context), 1));
+
+    lifter.blockInfo = BBInfo(0x2000, current);
+    lifter.visitedAddresses.insert(0x1000);
+    lifter.addrToBB[0x1000] = header;
+
+    if (lifter.canGeneralizeStructuredLoopHeader(0x1000)) {
+      details =
+          "  header with more than two predecessors must not be generalized as a structured loop\n";
       return false;
     }
     return true;
@@ -537,10 +711,23 @@ private:
              &InstructionTester::runScasRepeatPrefixesRejected);
     runCustom("loop_addrsize_override_rejected",
              &InstructionTester::runLoopAddressSizeOverrideRejected);
-    runCustom("loop_generalization_direct_jump_blocked",
-             &InstructionTester::runLoopGeneralizationDirectJumpBlocked);
+    runCustom("loop_generalization_conditional_branch_allowed",
+             &InstructionTester::runLoopGeneralizationConditionalBranchAllowed);
+    runCustom("loop_generalization_direct_jump_allowed",
+             &InstructionTester::runLoopGeneralizationDirectJumpAllowed);
     runCustom("loop_generalization_indirect_jump_blocked",
              &InstructionTester::runLoopGeneralizationIndirectJumpBlocked);
+    runCustom("loop_generalization_ret_blocked",
+             &InstructionTester::runLoopGeneralizationRetBlocked);
+    runCustom("structured_loop_header_allows_conditional_backedge",
+             &InstructionTester::runStructuredLoopHeaderAllowsConditionalBackedge);
+    runCustom("structured_loop_header_allows_jump_chain",
+             &InstructionTester::runStructuredLoopHeaderAllowsJumpChain);
+
+    runCustom("structured_loop_header_rejects_non_conditional_terminator",
+             &InstructionTester::runStructuredLoopHeaderRejectsNonConditionalTerminator);
+    runCustom("structured_loop_header_rejects_multiple_predecessors",
+             &InstructionTester::runStructuredLoopHeaderRejectsMultiplePredecessors);
     runCustom("generalized_loop_without_bypass_tag_keeps_normal_restore",
              &InstructionTester::runGeneralizedLoopWithoutBypassTagKeepsNormalRestore);
     runCustom("generalized_loop_with_bypass_tag_uses_generalized_restore",
diff --git a/scripts/rewrite/instruction_microtests.json b/scripts/rewrite/instruction_microtests.json
index b7b7a09..03e2796 100644
--- a/scripts/rewrite/instruction_microtests.json
+++ b/scripts/rewrite/instruction_microtests.json
@@ -100,9 +100,9 @@
       "patterns": [
         { "line_all": ["and i32", ", 1"] },
         { "line_all": ["and i32", ", 7"] },
-        "phi i64",
-        "select i1",
-        "icmp ugt i32",
+        "phi i32",
+        "add i32",
+        "sub i32",
         "br i1"
       ],
       "semantic": [
@@ -120,10 +120,10 @@
       "patterns": [
         { "line_all": ["and i32", ", 1"] },
         { "line_all": ["and i32", ", 7"] },
-        "select i1",
-        "phi i64",
-        "icmp ugt i32",
-        "br i1"
+        "phi i32",
+        "add i32",
+        "sub i32",
+        "ret i64 %common.ret.op"
       ],
       "semantic": [
         { "inputs": { "RCX": 0 }, "expected": 40, "label": "even program returns constant handler" },
@@ -137,17 +137,14 @@
     {
       "name": "stack_vm_loop",
       "symbol": "stack_vm_loop_target",
-      "skip": true,
-      "skip_reason": "Safe VMP-mode lifting currently disables loop-header generalization; this stack-based VM loop still exceeds the block budget without it.",
       "patterns": [
         { "line_all": ["and i32", ", 1"] },
         { "line_all": ["and i32", ", 7"] },
-        "switch i32",
         "phi i32",
-        "sub i32",
-        "select i1",
-        "add i32",
-        "ret i64"
+        "add nsw i32",
+        "mul i33",
+        "lshr exact i33",
+        "ret i64 %common.ret.op"
       ],
       "semantic": [
         { "inputs": { "RCX": 0 }, "expected": 40, "label": "even program returns constant handler" },
@@ -265,8 +262,6 @@
     {
       "name": "calc_sum_to_n",
       "symbol": "calc_sum_to_n",
-      "skip": true,
-      "skip_reason": "Safe VMP-mode lifting currently disables loop-header generalization; this counted-loop sample still explodes the block budget without it.",
       "patterns": ["phi i32", "icmp slt i32", "add i32", "br i1"],
       "semantic": [
         { "inputs": { "RCX": 0 },   "expected": 0,   "label": "n=0" },