diff --git a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/ssl/FileWatcher.java b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/ssl/FileWatcher.java
index eecad97b3b4e..9c4331dea493 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/ssl/FileWatcher.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/ssl/FileWatcher.java
@@ -86,7 +86,7 @@ void watch(Set<Path> paths, Runnable action) {
 					this.thread = new WatcherThread();
 					this.thread.start();
 				}
-				this.thread.register(new Registration(paths, action));
+				this.thread.register(new Registration(resolveSymlinks(paths), action));
 			}
 			catch (IOException ex) {
 				throw new UncheckedIOException("Failed to register paths for watching: " + paths, ex);
@@ -94,6 +94,14 @@ void watch(Set<Path> paths, Runnable action) {
 		}
 	}
 
+	private Set<Path> resolveSymlinks(Set<Path> paths) throws IOException {
+		Set<Path> result = new HashSet<>();
+		for (Path path : paths) {
+			result.add(Files.isSymbolicLink(path) ? Files.readSymbolicLink(path) : path);
+		}
+		return result;
+	}
+
 	@Override
 	public void close() throws IOException {
 		synchronized (this.lock) {
diff --git a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/ssl/FileWatcherTests.java b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/ssl/FileWatcherTests.java
index 5b3e18e3f79e..f0a2cc8b1674 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/ssl/FileWatcherTests.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/ssl/FileWatcherTests.java
@@ -94,6 +94,18 @@ void shouldWatchFile(@TempDir Path tempDir) throws Exception {
 		callback.expectChanges();
 	}
 
+	@Test
+	void shouldFollowSymlink(@TempDir Path tempDir) throws Exception {
+		Path realFile = tempDir.resolve("realFile.txt");
+		Path symLink = tempDir.resolve("symlink.txt");
+		Files.createFile(realFile);
+		Files.createSymbolicLink(symLink, realFile);
+		WaitingCallback callback = new WaitingCallback();
+		this.fileWatcher.watch(Set.of(symLink), callback);
+		Files.writeString(realFile, "Some content");
+		callback.expectChanges();
+	}
+
 	@Test
 	void shouldIgnoreNotWatchedFiles(@TempDir Path tempDir) throws Exception {
 		Path watchedFile = tempDir.resolve("watched.txt");