diff --git a/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtStyleTest.java b/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtStyleTest.java
index 7e448cc..d6eeade 100644
--- a/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtStyleTest.java
+++ b/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtStyleTest.java
@@ -20,6 +20,77 @@
 
 class JfmtStyleTest {
 
+    @Test
+    void keepsAdjacentBlockCommentsSeparatedAndStable() {
+        String input =
+                """
+                /*
+                 * License.
+                 */
+
+                /** Type documentation. */
+                class Example {}
+                """;
+
+        String formatted = JfmtTestSupport.format(input);
+
+        assertEquals(
+                """
+                /*
+                 * License.
+                 */
+                /** Type documentation. */
+                class Example {}
+                """,
+                formatted);
+        assertEquals(formatted, JfmtTestSupport.format(formatted));
+    }
+
+    @Test
+    void leavesAdjacentCommentMarkersInsideStringsUntouched() {
+        String input = "class Example {\n"
+                + "String value = \"*//**\";\n"
+                + "String text = \"\"\"\n"
+                + "*//**\n"
+                + "\"\"\";\n"
+                + "}\n";
+
+        String formatted = JfmtTestSupport.format(input);
+
+        assertEquals(2, formatted.split("\\*//\\*\\*", -1).length - 1);
+        assertEquals(formatted, JfmtTestSupport.format(formatted));
+    }
+
+    @Test
+    void keepsLongSwitchArmsStable() {
+        String input =
+                """
+                final class MavenCommand {
+                    private final ToolRuntime tools;
+                    private final List<ToolDefinition> definitions;
+                    private final ResolutionOptions javadocOptions;
+
+                    int run(JaInvocation commandLine, ModuleSourcePath moduleSourcePath, InputStream in,
+                            PrintStream out, PrintStream err)
+                            throws IOException {
+                        if (commandLine.toolArguments().isEmpty()) {
+                            throw new IllegalArgumentException("maven requires an operation: export, install, deploy, or deploy-central");
+                        }
+                        return switch (commandLine.toolArguments().getFirst()) {
+                            case "export" -> new MavenExporter(tools).run(commandLine, moduleSourcePath, in, out, err);
+                            case "install", "deploy", "deploy-central" -> new MavenDeploymentCommand(tools, definitions,
+                                    javadocOptions).run(commandLine, moduleSourcePath, in, out, err);
+                            default -> throw new IllegalArgumentException("Unknown maven operation: " + commandLine.toolArguments().getFirst());
+                        };
+                    }
+                }
+                """;
+
+        String formatted = JfmtTestSupport.format(input);
+
+        assertEquals(formatted, JfmtTestSupport.format(formatted));
+    }
+
     @Test
     void placesStaticImportsAfterOrdinaryImports() {
         String input = "import static java.util.Collections.emptyList;import sun.misc.Unsafe;import java.util.List;import jdk.internal.misc.VM;class Example{List<?> values=emptyList();Unsafe unsafe;Class<?> vm=VM.class;}";
diff --git a/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtToolTest.java b/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtToolTest.java
index 50ce303..97f2735 100644
--- a/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtToolTest.java
+++ b/src/com.netflix.tools.jfmt.test/com/netflix/tools/jfmt/test/JfmtToolTest.java
@@ -100,6 +100,36 @@ void expandsArgumentFiles() throws Exception {
         assertEquals("class Example {\n    int value;\n}\n", Files.readString(source));
     }
 
+    @Test
+    void formatsMultipleFilesIdempotently() throws Exception {
+        var files = new String[64];
+        for (int i = 0; i < files.length; i++) {
+            Path source = write(
+                    temporaryDirectory.resolve("Example" + i + ".java"),
+                    """
+                    class Example%d {
+                        int run(String operation) {
+                            return switch (operation) {
+                                case "install", "deploy", "deploy-central" -> new MavenDeploymentCommand(tools, definitions, javadocOptions)
+                                        .run(commandLine, moduleSourcePath, in, out, err);
+                                default -> 0;
+                            };
+                        }
+                    }
+                    """.formatted(i));
+            files[i] = source.toString();
+        }
+
+        Invocation formatted = run("", files);
+        var checkArguments = new String[files.length + 1];
+        checkArguments[0] = "--check";
+        System.arraycopy(files, 0, checkArguments, 1, files.length);
+        Invocation checked = run("", checkArguments);
+
+        assertEquals(0, formatted.exitCode(), formatted.error());
+        assertEquals(0, checked.exitCode(), checked.error());
+    }
+
     @Test
     void acceptsOptionsAfterFileOperands() throws Exception {
         Path source = write(temporaryDirectory.resolve("Example.java"), "class Example{int value;}");
diff --git a/src/com.netflix.tools.jfmt/classes/com/netflix/tools/jfmt/JfmtFormatter.java b/src/com.netflix.tools.jfmt/classes/com/netflix/tools/jfmt/JfmtFormatter.java
index ae17338..43f0c98 100644
--- a/src/com.netflix.tools.jfmt/classes/com/netflix/tools/jfmt/JfmtFormatter.java
+++ b/src/com.netflix.tools.jfmt/classes/com/netflix/tools/jfmt/JfmtFormatter.java
@@ -41,7 +41,83 @@ public JfmtFormatter() {
      * Format a Java source file, reorder imports, and remove unused imports.
      */
     public String formatSource(String input) throws FormatterException {
-        return formatter.formatSourceAndFixImports(input);
+        String formatted = separateAdjacentBlockComments(formatter.formatSourceAndFixImports(input));
+        for (int pass = 0; pass < 8; pass++) {
+            String next = separateAdjacentBlockComments(formatter.formatSource(formatted));
+            if (next.equals(formatted)) {
+                return formatted;
+            }
+            formatted = next;
+        }
+        throw new FormatterException("Formatting did not converge");
+    }
+
+    private static String separateAdjacentBlockComments(String input) {
+        var output = new StringBuilder(input.length());
+        String lineSeparator = input.contains("\r\n") ? "\r\n" : "\n";
+        var state = LexicalState.NORMAL;
+        for (int i = 0; i < input.length();) {
+            if (state == LexicalState.NORMAL && input.startsWith("\"\"\"", i)) {
+                output.append("\"\"\"");
+                i += 3;
+                state = LexicalState.TEXT_BLOCK;
+            } else if (state == LexicalState.NORMAL && input.startsWith("//", i)) {
+                output.append("//");
+                i += 2;
+                state = LexicalState.LINE_COMMENT;
+            } else if (state == LexicalState.NORMAL && input.startsWith("/*", i)) {
+                output.append("/*");
+                i += 2;
+                state = LexicalState.BLOCK_COMMENT;
+            } else if (state == LexicalState.NORMAL && input.charAt(i) == '"') {
+                output.append('"');
+                i++;
+                state = LexicalState.STRING;
+            } else if (state == LexicalState.NORMAL && input.charAt(i) == '\'') {
+                output.append('\'');
+                i++;
+                state = LexicalState.CHARACTER;
+            } else if ((state == LexicalState.STRING || state == LexicalState.CHARACTER || state == LexicalState.TEXT_BLOCK)
+                    && input.charAt(i) == '\\'
+                    && i + 1 < input.length()) {
+                output.append(input, i, i + 2);
+                i += 2;
+            } else if (state == LexicalState.STRING && input.charAt(i) == '"') {
+                output.append('"');
+                i++;
+                state = LexicalState.NORMAL;
+            } else if (state == LexicalState.CHARACTER && input.charAt(i) == '\'') {
+                output.append('\'');
+                i++;
+                state = LexicalState.NORMAL;
+            } else if (state == LexicalState.TEXT_BLOCK && input.startsWith("\"\"\"", i)) {
+                output.append("\"\"\"");
+                i += 3;
+                state = LexicalState.NORMAL;
+            } else if (state == LexicalState.LINE_COMMENT && (input.charAt(i) == '\n' || input.charAt(i) == '\r')) {
+                output.append(input.charAt(i++));
+                state = LexicalState.NORMAL;
+            } else if (state == LexicalState.BLOCK_COMMENT && input.startsWith("*/", i)) {
+                output.append("*/");
+                i += 2;
+                state = LexicalState.NORMAL;
+                if (input.startsWith("/*", i)) {
+                    output.append(lineSeparator);
+                }
+            } else {
+                output.append(input.charAt(i++));
+            }
+        }
+        return output.toString();
+    }
+
+    private enum LexicalState {
+        NORMAL,
+        STRING,
+        CHARACTER,
+        TEXT_BLOCK,
+        LINE_COMMENT,
+        BLOCK_COMMENT
     }
 
     /** Format specified character ranges of a Java source file. */