diff --git a/src/hotspot/share/opto/loopTransform.cpp b/src/hotspot/share/opto/loopTransform.cpp
index 94c781d82c2..0c03a85d64c 100644
--- a/src/hotspot/share/opto/loopTransform.cpp
+++ b/src/hotspot/share/opto/loopTransform.cpp
@@ -1970,8 +1970,19 @@ void PhaseIdealLoop::do_unroll(IdealLoopTree *loop, Node_List &old_new, bool adj
     if (opaq == nullptr) {
       return;
     }
-    // Zero-trip test uses an 'opaque' node which is not shared.
-    assert(opaq->outcnt() == 1 && opaq->in(1) == limit, "");
+    // Zero-trip test uses an 'opaque' node which is not shared, otherwise bail out.
+    if (opaq->outcnt() != 1 || opaq->in(1) != limit) {
+#ifdef ASSERT
+      // In rare cases, loop cloning (as for peeling, for instance) can break this by replacing
+      // limit and the input of opaq by equivalent but distinct phis.
+      // Next IGVN should clean it up. Let's try to detect we are in such a case.
+      Unique_Node_List& worklist = loop->_phase->_igvn._worklist;
+      assert(C->major_progress(), "The operation that replaced limit and opaq->in(1) (e.g. peeling) should have set major_progress");
+      assert(opaq->in(1)->is_Phi() && limit->is_Phi(), "Nodes limit and opaq->in(1) should have been replaced by PhiNodes by fix_data_uses from clone_loop.");
+      assert(worklist.member(opaq->in(1)) && worklist.member(limit), "Nodes limit and opaq->in(1) differ and should have been recorded for IGVN.");
+#endif
+      return;
+    }
   }
 
   C->set_major_progress();
diff --git a/src/hotspot/share/opto/loopnode.cpp b/src/hotspot/share/opto/loopnode.cpp
index b6c4d1b8574..54cf3e31266 100644
--- a/src/hotspot/share/opto/loopnode.cpp
+++ b/src/hotspot/share/opto/loopnode.cpp
@@ -4765,6 +4765,24 @@ void PhaseIdealLoop::eliminate_useless_zero_trip_guard() {
       Node* opaque = head->is_canonical_loop_entry();
       if (opaque != nullptr) {
         useful_zero_trip_guard_opaques_nodes.push(opaque);
+#ifdef ASSERT
+        // See PhaseIdealLoop::do_unroll
+        // This property is required in do_unroll, but it may not hold after cloning a loop.
+        // In such a case, we bail out from unrolling, and rely on IGVN to clean up the graph.
+        // We are here before loop cloning (before iteration_split), so if this property
+        // does not hold, it must come from the previous round of loop optimizations, meaning
+        // that IGVN failed to clean it: we will catch that here.
+        // On the other hand, if this assert passes, a bailout in do_unroll means that
+        // this property was broken in the current round of loop optimization (between here
+        // and do_unroll), so we give a chance to IGVN to make the property true again.
+        if (head->is_main_loop()) {
+          assert(opaque->outcnt() == 1, "opaque node should not be shared");
+          assert(opaque->in(1) == head->limit(), "After IGVN cleanup, input of opaque node must be the limit.");
+        }
+        if (head->is_post_loop()) {
+          assert(opaque->outcnt() == 1, "opaque node should not be shared");
+        }
+#endif
       }
     }
   }
diff --git a/test/hotspot/jtreg/compiler/loopopts/TooStrictAssertForUnrollAfterPeeling.java b/test/hotspot/jtreg/compiler/loopopts/TooStrictAssertForUnrollAfterPeeling.java
new file mode 100644
index 00000000000..edfab8822b5
--- /dev/null
+++ b/test/hotspot/jtreg/compiler/loopopts/TooStrictAssertForUnrollAfterPeeling.java
@@ -0,0 +1,194 @@
+/*
+ * Copyright (c) 2025, Oracle and/or its affiliates. All rights reserved.
+ * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS FILE HEADER.
+ *
+ * This code is free software; you can redistribute it and/or modify it
+ * under the terms of the GNU General Public License version 2 only, as
+ * published by the Free Software Foundation.
+ *
+ * This code is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or
+ * FITNESS FOR A PARTICULAR PURPOSE.  See the GNU General Public License
+ * version 2 for more details (a copy is included in the LICENSE file that
+ * accompanied this code).
+ *
+ * You should have received a copy of the GNU General Public License version
+ * 2 along with this work; if not, write to the Free Software Foundation,
+ * Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA.
+ *
+ * Please contact Oracle, 500 Oracle Parkway, Redwood Shores, CA 94065 USA
+ * or visit www.oracle.com if you need additional information or have any
+ * questions.
+ */
+
+/*
+ * @test
+ * @bug 8361608
+ * @summary crash during unrolling in some rare cases where loop cloning
+ *          (typically from peeling) breaks an invariant in do_unroll
+ *
+ * @run main/othervm -XX:+IgnoreUnrecognizedVMOptions
+ *                   -XX:+StressLoopPeeling
+ *                   -XX:CompileCommand=compileonly,compiler.loopopts.TooStrictAssertForUnrollAfterPeeling::test1
+ *                   -XX:-TieredCompilation
+ *                   -Xbatch
+ *                   -XX:PerMethodTrapLimit=0
+ *                   compiler.loopopts.TooStrictAssertForUnrollAfterPeeling
+ *
+ * @run main/othervm -XX:CompileOnly=compiler.loopopts.TooStrictAssertForUnrollAfterPeeling::test2
+ *                   -XX:-TieredCompilation
+ *                   -Xbatch
+ *                   -XX:PerMethodTrapLimit=0
+ *                   -XX:CompileCommand=inline,compiler.loopopts.TooStrictAssertForUnrollAfterPeeling::foo2
+ *                   compiler.loopopts.TooStrictAssertForUnrollAfterPeeling
+ *
+ * @run main/othervm -XX:CompileOnly=compiler.loopopts.TooStrictAssertForUnrollAfterPeeling::test3
+ *                   -XX:-TieredCompilation
+ *                   -Xbatch
+ *                   -XX:PerMethodTrapLimit=0
+ *                   -XX:CompileCommand=inline,compiler.loopopts.TooStrictAssertForUnrollAfterPeeling::foo3
+ *                   -XX:-RangeCheckElimination
+ *                   compiler.loopopts.TooStrictAssertForUnrollAfterPeeling
+ *
+ * @run main compiler.loopopts.TooStrictAssertForUnrollAfterPeeling
+ */
+package compiler.loopopts;
+
+
+/* Cases 2 and 3 can use the additional flags
+ *   -XX:+UnlockDiagnosticVMOptions
+ *   -XX:-LoopMultiversioning
+ *   -XX:-RangeCheckElimination
+ *   -XX:-SplitIfBlocks
+ *   -XX:-UseOnStackReplacement
+ *   -XX:LoopMaxUnroll=2
+ * to disable more optimizations and give a simpler graph, while still reproducing. It can be useful to debug, investigate...
+ */
+public class TooStrictAssertForUnrollAfterPeeling {
+    static int iArr[] = new int[400];
+    static boolean flag;
+
+    public static void main(String[] args) {
+        run1();
+        run2();
+        run3();
+    }
+
+    // Case 1
+
+    public static void run1() {
+        for (int i = 1; i < 1000; i++) {
+            test1();
+        }
+    }
+
+    static long test1() {
+        int s = 0;
+        int iArr[] = new int[400];
+        for (int i = 0; i < 70; i++) {}
+
+        for (int i = 0; i < 36; i++) {
+            for (int j = 0; j < 3; j++) {
+                s += iArr[0] = 7;
+                if (s != 0) {
+                    return s + foo1(iArr);
+                }
+            }
+        }
+        return 0;
+    }
+
+    public static long foo1(int[] a) {
+        long sum = 0;
+        for (int i = 0; i < a.length; i++) {
+            sum += a[i];
+        }
+        return sum;
+    }
+
+    // Case 2
+
+    public static void run2() {
+        for (int i = 1; i < 10000; i++) {
+            test2();
+        }
+    }
+
+    // Lx: Optimized in loop opts round x.
+
+    static int test2() {
+        int x = 5;
+        for (int i = 1; i < 37; i++) { // L3: Peeled
+            for (int a = 0; a < 2; a++) { // L2: Max unrolled
+                for (int b = 0; b < 300; b++) {
+                } // L1: Empty -> removed
+            }
+            int j = 1;
+            x *= 12;
+            while (++j < 5) { // L1: Max unrolled: peel + unroll
+                iArr[0] += 2;
+                if (iArr[0] > 0) {
+                    // foo(): everything outside loop.
+                    return foo2(iArr);
+                }
+            }
+        }
+        return 3;
+    }
+
+    public static int foo2(int[] a) {
+        int sum = 0;
+        for (int i = 0; i < a.length; i++) { // L2: Pre/main/post, L3: Unrolled -> hit assert!
+            for (int j = 0; j < 34; j++) {
+            } // L1: Empty -> removed
+            if (flag) {
+                // Ensure not directly unrolled in L2 but only in L3.
+                return 3;
+            }
+            sum += a[i];
+        }
+        return sum;
+    }
+
+    public static void run3() {
+        for (int i = 1; i < 10000; i++) {
+            test3();
+        }
+    }
+
+    // Case 3
+
+    static int test3() {
+        int x = 5;
+        for (int i = 1; i < 37; i++) { // L3: Peeled
+            for (int a = 0; a < 2; a++) { // L2: Max unrolled
+                for (int b = 0; b < 300; b++) {
+                } // L1: Empty -> removed
+            }
+            int j = 1;
+            x *= 12;
+            while (++j < 5) { // L1: Max unrolled: peel + unroll
+                iArr[0] += 2;
+                if (iArr[0] > 0) {
+                    // foo(): everything outside loop.
+                    return foo3(iArr, x);
+                }
+            }
+        }
+        return 3;
+    }
+
+    public static int foo3(int[] a, int limit) {
+        int sum = 0;
+        for (int i = 0; i < limit; i++) { // L2: Pre/main/post, L3: Unrolled -> hit assert!
+            for (int j = 0; j < 34; j++) {
+            } // L1: Empty -> removed
+            if (flag) {
+                // Ensure not directly unrolled in L2 but only in L3.
+                return 3;
+            }
+            sum += a[i];
+        }
+        return sum;
+    }
+}