diff --git a/rewrite-java-11/src/main/java/org/openrewrite/java/isolated/ReloadableJava11ParserVisitor.java b/rewrite-java-11/src/main/java/org/openrewrite/java/isolated/ReloadableJava11ParserVisitor.java
index 4c8b2709c6..9e7e360216 100644
--- a/rewrite-java-11/src/main/java/org/openrewrite/java/isolated/ReloadableJava11ParserVisitor.java
+++ b/rewrite-java-11/src/main/java/org/openrewrite/java/isolated/ReloadableJava11ParserVisitor.java
@@ -2186,6 +2186,7 @@ private ReloadableJava11ModifierResults sortedModifiersAndAnnotations(ModifiersT
         boolean afterFirstModifier = false;
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         final AtomicReference<String> word = new AtomicReference<>("");
         int afterLastModifierPosition = cursor;
         int lastAnnotationPosition = cursor;
@@ -2208,16 +2209,18 @@ private ReloadableJava11ModifierResults sortedModifiersAndAnnotations(ModifiersT
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
@@ -2321,6 +2324,7 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
         List<J.Annotation> annotations = new ArrayList<>();
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         for (int i = cursor; i <= maxAnnotationPosition && i < source.length(); i++) {
             if (annotationPosTable.containsKey(i)) {
                 JCAnnotation jcAnnotation = annotationPosTable.get(i);
@@ -2333,16 +2337,18 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && i > 0 && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
diff --git a/rewrite-java-17/src/main/java/org/openrewrite/java/isolated/ReloadableJava17ParserVisitor.java b/rewrite-java-17/src/main/java/org/openrewrite/java/isolated/ReloadableJava17ParserVisitor.java
index e857c8eddd..e19f03b369 100644
--- a/rewrite-java-17/src/main/java/org/openrewrite/java/isolated/ReloadableJava17ParserVisitor.java
+++ b/rewrite-java-17/src/main/java/org/openrewrite/java/isolated/ReloadableJava17ParserVisitor.java
@@ -2341,6 +2341,7 @@ private ReloadableJava17ModifierResults sortedModifiersAndAnnotations(ModifiersT
         boolean afterFirstModifier = false;
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         int afterLastModifierPosition = cursor;
         int lastAnnotationPosition = cursor;
 
@@ -2362,16 +2363,18 @@ private ReloadableJava17ModifierResults sortedModifiersAndAnnotations(ModifiersT
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
@@ -2473,6 +2476,7 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
         List<J.Annotation> annotations = new ArrayList<>();
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         for (int i = cursor; i <= maxAnnotationPosition && i < source.length(); i++) {
             if (annotationPosTable.containsKey(i)) {
                 JCAnnotation jcAnnotation = annotationPosTable.get(i);
@@ -2485,16 +2489,18 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && i > 0 && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
diff --git a/rewrite-java-21/src/main/java/org/openrewrite/java/isolated/ReloadableJava21ParserVisitor.java b/rewrite-java-21/src/main/java/org/openrewrite/java/isolated/ReloadableJava21ParserVisitor.java
index cd3892c049..5060e081b6 100644
--- a/rewrite-java-21/src/main/java/org/openrewrite/java/isolated/ReloadableJava21ParserVisitor.java
+++ b/rewrite-java-21/src/main/java/org/openrewrite/java/isolated/ReloadableJava21ParserVisitor.java
@@ -2379,6 +2379,7 @@ private ReloadableJava21ModifierResults sortedModifiersAndAnnotations(ModifiersT
         boolean afterFirstModifier = false;
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         int afterLastModifierPosition = cursor;
         int lastAnnotationPosition = cursor;
 
@@ -2400,16 +2401,18 @@ private ReloadableJava21ModifierResults sortedModifiersAndAnnotations(ModifiersT
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
@@ -2511,6 +2514,7 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
         List<J.Annotation> annotations = new ArrayList<>();
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         for (int i = cursor; i <= maxAnnotationPosition && i < source.length(); i++) {
             if (annotationPosTable.containsKey(i)) {
                 JCAnnotation jcAnnotation = annotationPosTable.get(i);
@@ -2523,16 +2527,18 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && i > 0 && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
diff --git a/rewrite-java-25/src/main/java/org/openrewrite/java/isolated/ReloadableJava25ParserVisitor.java b/rewrite-java-25/src/main/java/org/openrewrite/java/isolated/ReloadableJava25ParserVisitor.java
index 22c3fbe09f..1ec18d89c0 100644
--- a/rewrite-java-25/src/main/java/org/openrewrite/java/isolated/ReloadableJava25ParserVisitor.java
+++ b/rewrite-java-25/src/main/java/org/openrewrite/java/isolated/ReloadableJava25ParserVisitor.java
@@ -2411,6 +2411,7 @@ private ReloadableJava25ModifierResults sortedModifiersAndAnnotations(ModifiersT
         boolean afterFirstModifier = false;
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         int afterLastModifierPosition = cursor;
         int lastAnnotationPosition = cursor;
 
@@ -2432,16 +2433,18 @@ private ReloadableJava25ModifierResults sortedModifiersAndAnnotations(ModifiersT
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
@@ -2543,6 +2546,7 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
         List<J.Annotation> annotations = new ArrayList<>();
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         for (int i = cursor; i <= maxAnnotationPosition && i < source.length(); i++) {
             if (annotationPosTable.containsKey(i)) {
                 JCAnnotation jcAnnotation = annotationPosTable.get(i);
@@ -2555,16 +2559,18 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && i > 0 && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
diff --git a/rewrite-java-8/src/main/java/org/openrewrite/java/ReloadableJava8ParserVisitor.java b/rewrite-java-8/src/main/java/org/openrewrite/java/ReloadableJava8ParserVisitor.java
index 719cb1271c..1a8cc07007 100644
--- a/rewrite-java-8/src/main/java/org/openrewrite/java/ReloadableJava8ParserVisitor.java
+++ b/rewrite-java-8/src/main/java/org/openrewrite/java/ReloadableJava8ParserVisitor.java
@@ -2168,6 +2168,7 @@ private Java8ModifierResults sortedModifiersAndAnnotations(ModifiersTree modifie
         boolean afterFirstModifier = false;
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         final AtomicReference<String> word = new AtomicReference<>("");
         int afterLastModifierPosition = cursor;
         int lastAnnotationPosition = cursor;
@@ -2190,16 +2191,18 @@ private Java8ModifierResults sortedModifiersAndAnnotations(ModifiersTree modifie
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
@@ -2303,6 +2306,7 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
         List<J.Annotation> annotations = new ArrayList<>();
         boolean inComment = false;
         boolean inMultilineComment = false;
+        int multilineCommentStart = -1;
         for (int i = cursor; i <= maxAnnotationPosition && i < source.length(); i++) {
             if (annotationPosTable.containsKey(i)) {
                 JCAnnotation jcAnnotation = annotationPosTable.get(i);
@@ -2315,16 +2319,18 @@ private List<J.Annotation> collectAnnotations(Map<Integer, JCAnnotation> annotat
                 continue;
             }
             char c = source.charAt(i);
-            if (c == '/' && source.length() > i + 1) {
+            if (c == '/' && source.length() > i + 1 && !inComment && !inMultilineComment) {
                 char next = source.charAt(i + 1);
                 if (next == '*') {
                     inMultilineComment = true;
+                    multilineCommentStart = i;
                 } else if (next == '/') {
                     inComment = true;
                 }
             }
 
-            if (inMultilineComment && c == '/' && i > 0 && source.charAt(i - 1) == '*') {
+            // The closing `/` cannot be part of the opener, so `/*/` does not terminate a block comment.
+            if (inMultilineComment && c == '/' && i >= multilineCommentStart + 3 && source.charAt(i - 1) == '*') {
                 inMultilineComment = false;
             } else if (inComment && (c == '\n' || c == '\r')) {
                 inComment = false;
diff --git a/rewrite-java-tck/src/main/java/org/openrewrite/java/tree/CommentTest.java b/rewrite-java-tck/src/main/java/org/openrewrite/java/tree/CommentTest.java
index 2cc970f222..fa9410542f 100644
--- a/rewrite-java-tck/src/main/java/org/openrewrite/java/tree/CommentTest.java
+++ b/rewrite-java-tck/src/main/java/org/openrewrite/java/tree/CommentTest.java
@@ -52,6 +52,82 @@ class Test {// /*
         );
     }
 
+    @Test
+    void multilineOpenerInsideSingleLineCommentBeforeMethodModifier() {
+        rewriteRun(
+          java(
+            """
+              class Test {
+                  @Deprecated  //*not a block comment
+                  public String value() {
+                      return null;
+                  }
+              }
+              """
+          )
+        );
+    }
+
+    @Test
+    void multilineOpenerInsideSingleLineCommentBeforeMultipleModifiers() {
+        rewriteRun(
+          java(
+            """
+              class Test {
+                  @Deprecated  //*not a block comment
+                  public static String value() {
+                      return null;
+                  }
+              }
+              """
+          )
+        );
+    }
+
+    @Test
+    void multilineOpenerLaterInSingleLineCommentBeforeFieldModifier() {
+        rewriteRun(
+          java(
+            """
+              class Test {
+                  @Deprecated  //see /*.java
+                  public int value = 1;
+              }
+              """
+          )
+        );
+    }
+
+    @Test
+    void slashImmediatelyAfterMultilineOpenerBeforeModifier() {
+        rewriteRun(
+          java(
+            """
+              class Test {
+                  @Deprecated /*/ not the end of the comment */ public String value() {
+                      return null;
+                  }
+              }
+              """
+          )
+        );
+    }
+
+    @Test
+    void singleLineOpenerInsideMultilineCommentBeforeModifiers() {
+        rewriteRun(
+          java(
+            """
+              class Test {
+                  @Deprecated /* // */ public static String value() {
+                      return null;
+                  }
+              }
+              """
+          )
+        );
+    }
+
     @Issue("https://github.com/openrewrite/rewrite/issues/4995")
     @Test
     void trailingComment() {