diff --git a/src/Razor/Microsoft.AspNetCore.Razor.Tools/src/RewriteCssCommand.cs b/src/Razor/Microsoft.AspNetCore.Razor.Tools/src/RewriteCssCommand.cs
index 6369d3bc93..f9e33cae14 100644
--- a/src/Razor/Microsoft.AspNetCore.Razor.Tools/src/RewriteCssCommand.cs
+++ b/src/Razor/Microsoft.AspNetCore.Razor.Tools/src/RewriteCssCommand.cs
@@ -6,6 +6,7 @@ using System.Collections.Generic;
 using System.IO;
 using System.Linq;
 using System.Text;
+using System.Text.RegularExpressions;
 using System.Threading.Tasks;
 using Microsoft.Css.Parser.Parser;
 using Microsoft.Css.Parser.Tokens;
@@ -18,6 +19,11 @@ namespace Microsoft.AspNetCore.Razor.Tools
 {
     internal class RewriteCssCommand : CommandBase
     {
+        private const string DeepCombinatorText = "::deep";
+        private readonly static TimeSpan _regexTimeout = TimeSpan.FromSeconds(1);
+        private readonly static Regex _deepCombinatorRegex = new Regex($@"^{DeepCombinatorText}\s*", RegexOptions.None, _regexTimeout);
+        private readonly static Regex _trailingCombinatorRegex = new Regex(@"\s+[\>\+\~]$", RegexOptions.None, _regexTimeout);
+
         public RewriteCssCommand(Application parent)
             : base(parent, "rewritecss")
         {
@@ -145,12 +151,12 @@ namespace Microsoft.AspNetCore.Razor.Tools
                 // If there's a deep combinator among the sequence of simple selectors, we consider that to signal
                 // the end of the set of simple selectors for us to look at, plus we strip it out
                 var allSimpleSelectors = selector.Children.OfType<SimpleSelector>();
-                var firstDeepCombinator = allSimpleSelectors.FirstOrDefault(s => IsDeepCombinator(s.Text));
+                var firstDeepCombinator = allSimpleSelectors.FirstOrDefault(s => _deepCombinatorRegex.IsMatch(s.Text));
 
                 var lastSimpleSelector = allSimpleSelectors.TakeWhile(s => s != firstDeepCombinator).LastOrDefault();
                 if (lastSimpleSelector != null)
                 {
-                    Edits.Add(new InsertSelectorScopeEdit { Position = lastSimpleSelector.AfterEnd });
+                    Edits.Add(new InsertSelectorScopeEdit { Position = FindPositionBeforeTrailingCombinator(lastSimpleSelector) });
                 }
                 else if (firstDeepCombinator != null)
                 {
@@ -162,13 +168,32 @@ namespace Microsoft.AspNetCore.Razor.Tools
                 // Also remove the deep combinator if we matched one
                 if (firstDeepCombinator != null)
                 {
-                    Edits.Add(new DeleteContentEdit { Position = firstDeepCombinator.Start, DeleteLength = firstDeepCombinator.Length });
+                    Edits.Add(new DeleteContentEdit { Position = firstDeepCombinator.Start, DeleteLength = DeepCombinatorText.Length });
                 }
             }
 
-            private static bool IsDeepCombinator(string simpleSelectorText)
+            private int FindPositionBeforeTrailingCombinator(SimpleSelector lastSimpleSelector)
             {
-                return string.Equals(simpleSelectorText, "::deep", StringComparison.Ordinal);
+                // For a selector like "a > ::deep b", the parser splits it as "a >", "::deep", "b".
+                // The place we want to insert the scope is right after "a", hence we need to detect
+                // if the simple selector ends with " >" or similar, and if so, insert before that.
+                var text = lastSimpleSelector.Text;
+                var lastChar = text.Length > 0 ? text[^1] : default;
+                switch (lastChar)
+                {
+                    case '>':
+                    case '+':
+                    case '~':
+                        var trailingCombinatorMatch = _trailingCombinatorRegex.Match(text);
+                        if (trailingCombinatorMatch.Success)
+                        {
+                            var trailingCombinatorLength = trailingCombinatorMatch.Length;
+                            return lastSimpleSelector.AfterEnd - trailingCombinatorLength;
+                        }
+                        break;
+                }
+
+                return lastSimpleSelector.AfterEnd;
             }
 
             protected override void VisitAtDirective(AtDirective item)
diff --git a/src/Razor/Microsoft.AspNetCore.Razor.Tools/test/RewriteCssCommandTest.cs b/src/Razor/Microsoft.AspNetCore.Razor.Tools/test/RewriteCssCommandTest.cs
index 57d8830a52..2c2d199f80 100644
--- a/src/Razor/Microsoft.AspNetCore.Razor.Tools/test/RewriteCssCommandTest.cs
+++ b/src/Razor/Microsoft.AspNetCore.Razor.Tools/test/RewriteCssCommandTest.cs
@@ -91,6 +91,54 @@ namespace Microsoft.AspNetCore.Razor.Tools
 ", result);
         }
 
+        [Fact]
+        public void RespectsDeepCombinatorWithDirectDescendant()
+        {
+            // Arrange/act
+            var result = RewriteCssCommand.AddScopeToSelectors(@"
+    a  >  ::deep b { color: red; }
+    c ::deep  >  d { color: blue; }
+", "TestScope");
+
+            // Assert
+            Assert.Equal(@"
+    a[TestScope]  >   b { color: red; }
+    c[TestScope]   >  d { color: blue; }
+", result);
+        }
+
+        [Fact]
+        public void RespectsDeepCombinatorWithAdjacentSibling()
+        {
+            // Arrange/act
+            var result = RewriteCssCommand.AddScopeToSelectors(@"
+    a + ::deep b { color: red; }
+    c ::deep + d { color: blue; }
+", "TestScope");
+
+            // Assert
+            Assert.Equal(@"
+    a[TestScope] +  b { color: red; }
+    c[TestScope]  + d { color: blue; }
+", result);
+        }
+
+        [Fact]
+        public void RespectsDeepCombinatorWithGeneralSibling()
+        {
+            // Arrange/act
+            var result = RewriteCssCommand.AddScopeToSelectors(@"
+    a ~ ::deep b { color: red; }
+    c ::deep ~ d { color: blue; }
+", "TestScope");
+
+            // Assert
+            Assert.Equal(@"
+    a[TestScope] ~  b { color: red; }
+    c[TestScope]  ~ d { color: blue; }
+", result);
+        }
+
         [Fact]
         public void IgnoresMultipleDeepCombinators()
         {