diff --git a/CHANGES.md b/CHANGES.md
index fc7c59fab0..92cd0de430 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -7,6 +7,9 @@ You might be looking for:
 
 ### Version 1.26.0-SNAPSHOT - TBD (javadoc [lib](https://diffplug.github.io/spotless/javadoc/spotless-lib/snapshot/) [lib-extra](https://diffplug.github.io/spotless/javadoc/spotless-lib-extra/snapshot/), [snapshot repo](https://oss.sonatype.org/content/repositories/snapshots/com/diffplug/spotless/))
 
+* Fix `ImportSorter` crashing with empty files. ([#474](https://github.com/diffplug/spotless/pull/474))
+  * Fixes [#305](https://github.com/diffplug/spotless/issues/305) StringIndexOutOfBoundsException for empty Groovy file when performing importOrder
+
 ### Version 1.25.0 - October 6th 2019 (javadoc [lib](https://diffplug.github.io/spotless/javadoc/spotless-lib/1.25.0/) [lib-extra](https://diffplug.github.io/spotless/javadoc/spotless-lib-extra/1.25.0/), artifact [lib]([jcenter](https://bintray.com/diffplug/opensource/spotless-lib), [lib-extra]([jcenter](https://bintray.com/diffplug/opensource/spotless-lib-extra)))
 
 * Add support for ktlint `0.34+`, and bump default version from `0.32.0` to `0.34.2`. ([#469](https://github.com/diffplug/spotless/pull/469))
diff --git a/lib/src/main/java/com/diffplug/spotless/java/ImportSorter.java b/lib/src/main/java/com/diffplug/spotless/java/ImportSorter.java
index 3c532182b5..b522f748cc 100644
--- a/lib/src/main/java/com/diffplug/spotless/java/ImportSorter.java
+++ b/lib/src/main/java/com/diffplug/spotless/java/ImportSorter.java
@@ -92,6 +92,9 @@ private static boolean isBeginningOfScope(String line) {
 	}
 
 	private static String applyImportsToDocument(final String document, int firstImportLine, int lastImportLine, List<String> strings) {
+		if (document.isEmpty()) {
+			return document;
+		}
 		boolean importsAlreadyAppended = false;
 		Scanner scanner = new Scanner(document);
 		int curentLine = 0;
diff --git a/plugin-gradle/CHANGES.md b/plugin-gradle/CHANGES.md
index 12449abc2a..2a5185aec3 100644
--- a/plugin-gradle/CHANGES.md
+++ b/plugin-gradle/CHANGES.md
@@ -2,6 +2,9 @@
 
 ### Version 3.26.0-SNAPSHOT - TBD ([javadoc](https://diffplug.github.io/spotless/javadoc/snapshot/), [snapshot](https://oss.sonatype.org/content/repositories/snapshots/com/diffplug/spotless/spotless-plugin-gradle/))
 
+* Fix `ImportSorter` crashing with empty files. ([#474](https://github.com/diffplug/spotless/pull/474))
+  * Fixes [#305](https://github.com/diffplug/spotless/issues/305) StringIndexOutOfBoundsException for empty Groovy file when performing importOrder
+
 ### Version 3.25.0 - October 6th 2019 ([javadoc](https://diffplug.github.io/spotless/javadoc/spotless-plugin-gradle/3.25.0/), [jcenter](https://bintray.com/diffplug/opensource/spotless-plugin-gradle/3.25.0))
 
 * Spotless no longer breaks configuration avoidance for other tasks (specifically the `check` task and all of its dependees) ([#463](https://github.com/diffplug/spotless/pull/463)).
diff --git a/plugin-maven/CHANGES.md b/plugin-maven/CHANGES.md
index 447ac18d70..bd84ee469e 100644
--- a/plugin-maven/CHANGES.md
+++ b/plugin-maven/CHANGES.md
@@ -2,6 +2,9 @@
 
 ### Version 1.26.0-SNAPSHOT - TBD ([javadoc](https://diffplug.github.io/spotless/javadoc/spotless-maven-plugin/snapshot/), [snapshot](https://oss.sonatype.org/content/repositories/snapshots/com/diffplug/spotless/spotless-maven-plugin/))
 
+* Fix `ImportSorter` crashing with empty files. ([#474](https://github.com/diffplug/spotless/pull/474))
+  * Fixes [#305](https://github.com/diffplug/spotless/issues/305) StringIndexOutOfBoundsException for empty Groovy file when performing importOrder
+
 ### Version 1.25.1 - October 7th 2019 ([javadoc](https://diffplug.github.io/spotless/javadoc/spotless-maven-plugin/1.25.1/), [jcenter](https://bintray.com/diffplug/opensource/spotless-maven-plugin/1.25.1))
 
 * Fixed problem which could cause a stale `.jar` to be published. ([#471](https://github.com/diffplug/spotless/pull/471))
diff --git a/testlib/src/main/resources/java/importsorter/JavaCodeEmptyFile.test b/testlib/src/main/resources/java/importsorter/JavaCodeEmptyFile.test
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/testlib/src/test/java/com/diffplug/spotless/java/ImportOrderStepTest.java b/testlib/src/test/java/com/diffplug/spotless/java/ImportOrderStepTest.java
index 243c951f55..845aea31da 100644
--- a/testlib/src/test/java/com/diffplug/spotless/java/ImportOrderStepTest.java
+++ b/testlib/src/test/java/com/diffplug/spotless/java/ImportOrderStepTest.java
@@ -59,6 +59,12 @@ public void misplacedImports() throws Throwable {
 		assertOnResources(step, "java/importsorter/JavaCodeUnsortedMisplacedImports.test", "java/importsorter/JavaCodeSortedMisplacedImports.test");
 	}
 
+	@Test
+	public void empty() throws Throwable {
+		FormatterStep step = ImportOrderStep.forJava().createFrom(createTestFile("java/importsorter/import.properties"));
+		assertOnResources(step, "java/importsorter/JavaCodeEmptyFile.test", "java/importsorter/JavaCodeEmptyFile.test");
+	}
+
 	@Test
 	public void groovyImports() throws Throwable {
 		FormatterStep step = ImportOrderStep.forGroovy().createFrom(createTestFile("java/importsorter/import.properties"));