diff --git a/src/main/java/org/openrewrite/java/migrate/lang/UseTextBlocks.java b/src/main/java/org/openrewrite/java/migrate/lang/UseTextBlocks.java
index 2d6a5b7989..7a5a234e32 100644
--- a/src/main/java/org/openrewrite/java/migrate/lang/UseTextBlocks.java
+++ b/src/main/java/org/openrewrite/java/migrate/lang/UseTextBlocks.java
@@ -125,7 +125,9 @@ private J.Literal toTextBlock(J.Binary binary, String content, List<J.Literal> s
 
                 StringBuilder sb = new StringBuilder();
                 StringBuilder originalContent = new StringBuilder();
-                stringLiterals = stringLiterals.stream().filter(s -> s.getValue() != null && !s.getValue().toString().isEmpty()).collect(Collectors.toList());
+                stringLiterals = stringLiterals.stream()
+                        .filter(s -> s.getValue() != null && !s.getValue().toString().isEmpty())
+                        .collect(Collectors.toList());
                 for (int i = 0; i < stringLiterals.size(); i++) {
                     String s = requireNonNull(stringLiterals.get(i).getValue()).toString();
                     sb.append(s);
@@ -139,8 +141,6 @@ private J.Literal toTextBlock(J.Binary binary, String content, List<J.Literal> s
                     }
                 }
 
-                content = sb.toString();
-
                 TabsAndIndentsStyle tabsAndIndentsStyle = Optional.ofNullable(getCursor().firstEnclosingOrThrow(SourceFile.class)
                         .getStyle(TabsAndIndentsStyle.class)).orElse(IntelliJ.tabsAndIndents());
                 boolean useTab = tabsAndIndentsStyle.getUseTabCharacter();
@@ -148,12 +148,11 @@ private J.Literal toTextBlock(J.Binary binary, String content, List<J.Literal> s
 
                 String indentation = getIndents(concatenation, useTab, tabSize);
 
-                boolean isEndsWithNewLine = content.endsWith("\n");
-
                 // references:
                 //  - https://docs.oracle.com/en/java/javase/14/docs/specs/text-blocks-jls.html
                 //  - https://javaalmanac.io/features/textblocks/
 
+                content = sb.toString();
                 // escape backslashes
                 content = content.replace("\\", "\\\\");
                 // escape triple quotes
@@ -170,13 +169,20 @@ private J.Literal toTextBlock(J.Binary binary, String content, List<J.Literal> s
 
                 // add last line to ensure the closing delimiter is in a new line to manage indentation & remove the
                 // need to escape ending quote in the content
-                if (!isEndsWithNewLine) {
+                if (isEndsWithSpecialCharacters(sb.toString())) {
                     content = content + "\\\n" + indentation;
                 }
 
                 return new J.Literal(randomId(), binary.getPrefix(), Markers.EMPTY, originalContent.toString(),
                         String.format("\"\"\"%s\"\"\"", content), null, JavaType.Primitive.String);
             }
+
+            private boolean isEndsWithSpecialCharacters(String content) {
+                return content.endsWith("\"") ||
+                       content.endsWith("=") ||
+                       content.endsWith("}") ||
+                       content.endsWith(";");
+            }
         });
     }
 
diff --git a/src/test/java/org/openrewrite/java/migrate/lang/UseTextBlocksTest.java b/src/test/java/org/openrewrite/java/migrate/lang/UseTextBlocksTest.java
index 8cc9d71d21..995e9acd8a 100644
--- a/src/test/java/org/openrewrite/java/migrate/lang/UseTextBlocksTest.java
+++ b/src/test/java/org/openrewrite/java/migrate/lang/UseTextBlocksTest.java
@@ -88,8 +88,7 @@ class Test {
                       String query = \"""
                           SELECT * FROM   \\s
                           my_table   \\s
-                          WHERE something = 1; \\
-                          \""";
+                          WHERE something = 1; \""";
               }
               """
           )
@@ -738,8 +737,7 @@ class Test {
               class Test {
                   String eightQuotes = ""\"
                                  ""\\""\"\\""\"\\
-                                 after 8 quotes\\
-                                 ""\";
+                                 after 8 quotes""\";
               }
               """
           )
@@ -860,4 +858,30 @@ void shouldNotUpdateKotlinCode() {
           )
         );
     }
+
+    @Test
+    @Issue("https://github.com/openrewrite/rewrite-migrate-java/issues/555")
+    void textBlockTrailingEscape() {
+        rewriteRun(
+          spec -> spec.recipe(new UseTextBlocks()),
+          java(
+            """
+             package com.helloworld;
+
+             public class Main {
+                 String foo =
+                     "hello\\n"
+                         + "world";
+            }""",
+            """
+             package com.helloworld;
+
+             public class Main {
+                 String foo =
+                     \"""
+                     hello
+                     world\""";
+            }""",
+            src -> src.markers(javaVersion(17))));
+    }
 }