diff --git a/src/Markdig.Tests/TestEmphasisExtended.cs b/src/Markdig.Tests/TestEmphasisExtended.cs
index ce6c8973..c95fc5e3 100644
--- a/src/Markdig.Tests/TestEmphasisExtended.cs
+++ b/src/Markdig.Tests/TestEmphasisExtended.cs
@@ -148,6 +148,9 @@ class CustomEmphasisInline : EmphasisInline { }
     [TestCase("1Foo1",          "<one-only>Foo</one-only>")]
     [TestCase("1121",           "1<one-only>2</one-only>")]
     [TestCase("22322",          "<two-only>3</two-only>")]
+    [TestCase("2223222",        "2<two-only>32</two-only>")]
+    [TestCase("22223222",       "22<two-only>32</two-only>")]
+    [TestCase("22223223222",    "22223<two-only>3</two-only>2")]
     [TestCase("2232",           "2232")]
     [TestCase("333",            "333")]
     [TestCase("3334333",        "<three-only>4</three-only>")]
diff --git a/src/Markdig/Helpers/UnicodeUtility.cs b/src/Markdig/Helpers/UnicodeUtility.cs
index 4364c953..2c059afc 100644
--- a/src/Markdig/Helpers/UnicodeUtility.cs
+++ b/src/Markdig/Helpers/UnicodeUtility.cs
@@ -22,7 +22,7 @@ public static bool IsValidUnicodeScalar(uint value)
     [MethodImpl(MethodImplOptions.AggressiveInlining)]
     public static void GetUtf16SurrogatesFromSupplementaryPlaneScalar(uint value, out char highSurrogateCodePoint, out char lowSurrogateCodePoint)
     {
-        Debug.Assert(IsValidUnicodeScalar(value) && IsBmpCodePoint(value));
+        Debug.Assert(IsValidUnicodeScalar(value) && !IsBmpCodePoint(value));
 
         highSurrogateCodePoint = (char)((value + ((0xD800u - 0x40u) << 10)) >> 10);
         lowSurrogateCodePoint = (char)((value & 0x3FFu) + 0xDC00u);
diff --git a/src/Markdig/Parsers/Inlines/EmphasisDescriptor.cs b/src/Markdig/Parsers/Inlines/EmphasisDescriptor.cs
index c2e8259e..429a24b1 100644
--- a/src/Markdig/Parsers/Inlines/EmphasisDescriptor.cs
+++ b/src/Markdig/Parsers/Inlines/EmphasisDescriptor.cs
@@ -3,12 +3,14 @@
 // See the license.txt file in the project root for more information.
 
 using Markdig.Helpers;
+using System.Diagnostics;
 
 namespace Markdig.Parsers.Inlines;
 
 /// <summary>
 /// Descriptor for an emphasis.
 /// </summary>
+[DebuggerDisplay("Emphasis Char={Character}, Min={MinimumCount}, Max={MaximumCount}, EnableWithinWord={EnableWithinWord}")]
 public sealed class EmphasisDescriptor
 {
     /// <summary>
diff --git a/src/Markdig/Parsers/Inlines/EmphasisInlineParser.cs b/src/Markdig/Parsers/Inlines/EmphasisInlineParser.cs
index 440a878b..af2921c8 100644
--- a/src/Markdig/Parsers/Inlines/EmphasisInlineParser.cs
+++ b/src/Markdig/Parsers/Inlines/EmphasisInlineParser.cs
@@ -233,9 +233,9 @@ private void ProcessEmphasis(InlineProcessor processor, List<EmphasisDelimiterIn
                 continue;
             }
 
-            if ((closeDelimiter.Type & DelimiterType.Close) != 0 && closeDelimiter.DelimiterCount >= emphasisDesc.MinimumCount)
+            if ((closeDelimiter.Type & DelimiterType.Close) != 0)
             {
-                while (true)
+                while (closeDelimiter.DelimiterCount >= emphasisDesc.MinimumCount)
                 {
                     // Now, look back in the stack (staying above stack_bottom and the openers_bottom for this delimiter type)
                     // for the first matching potential opener (“matching” means same delimiter).
@@ -245,8 +245,7 @@ private void ProcessEmphasis(InlineProcessor processor, List<EmphasisDelimiterIn
                     {
                         var previousOpenDelimiter = delimiters[j];
 
-                        var isOddMatch = ((closeDelimiter.Type & DelimiterType.Open) != 0 ||
-                                         (previousOpenDelimiter.Type & DelimiterType.Close) != 0) &&
+                        var isOddMatch = ((closeDelimiter.Type & DelimiterType.Open) != 0 || (previousOpenDelimiter.Type & DelimiterType.Close) != 0) &&
                                          previousOpenDelimiter.DelimiterCount != closeDelimiter.DelimiterCount &&
                                          (previousOpenDelimiter.DelimiterCount + closeDelimiter.DelimiterCount) % 3 == 0 &&
                                          (previousOpenDelimiter.DelimiterCount % 3 != 0 || closeDelimiter.DelimiterCount % 3 != 0);
@@ -357,7 +356,8 @@ private void ProcessEmphasis(InlineProcessor processor, List<EmphasisDelimiterIn
                         }
 
                         // The current delimiters are matching
-                        if (openDelimiter.DelimiterCount >= emphasisDesc.MinimumCount)
+                        if (openDelimiter.DelimiterCount >= emphasisDesc.MinimumCount &&
+                            closeDelimiter.DelimiterCount >= emphasisDesc.MinimumCount)
                         {
                             goto process_delims;
                         }