diff --git a/CHANGES.md b/CHANGES.md
index 89bc6a1231..bc19d79cf5 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -10,6 +10,8 @@ This document is intended for Spotless developers.
 We adhere to the [keepachangelog](https://keepachangelog.com/en/1.0.0/) format (starting after version `1.27.0`).
 
 ## [Unreleased]
+### Changed
+* When applying license headers for the first time, we are now more lenient about parsing existing years from the header ([#690](https://github.com/diffplug/spotless/pull/690)).
 
 ## [2.5.0] - 2020-09-08
 ### Added
diff --git a/lib/src/main/java/com/diffplug/spotless/generic/LicenseHeaderStep.java b/lib/src/main/java/com/diffplug/spotless/generic/LicenseHeaderStep.java
index 3066113d3b..40eee8a6f4 100644
--- a/lib/src/main/java/com/diffplug/spotless/generic/LicenseHeaderStep.java
+++ b/lib/src/main/java/com/diffplug/spotless/generic/LicenseHeaderStep.java
@@ -181,8 +181,6 @@ private Runtime(String licenseHeader, String delimiter, String yearSeparator, bo
 			}
 		}
 
-		private static final Pattern patternYearSingle = Pattern.compile("[0-9]{4}");
-
 		/**
 		 * Get the first place holder token being used in the
 		 * license header for specifying the year
@@ -200,6 +198,7 @@ private String format(String raw) {
 			if (!contentMatcher.find()) {
 				throw new IllegalArgumentException("Unable to find delimiter regex " + delimiterPattern);
 			} else {
+				String content = raw.substring(contentMatcher.start());
 				if (yearToday == null) {
 					// the no year case is easy
 					if (contentMatcher.start() == yearSepOrFull.length() && raw.startsWith(yearSepOrFull)) {
@@ -208,7 +207,7 @@ private String format(String raw) {
 						return raw;
 					} else {
 						// otherwise we'll have to add the header
-						return yearSepOrFull + raw.substring(contentMatcher.start());
+						return yearSepOrFull + content;
 					}
 				} else {
 					// the yes year case is a bit harder
@@ -216,47 +215,65 @@ private String format(String raw) {
 					int afterYearIdx = raw.indexOf(afterYear, beforeYearIdx + beforeYear.length() + 1);
 
 					if (beforeYearIdx >= 0 && afterYearIdx >= 0 && afterYearIdx + afterYear.length() <= contentMatcher.start()) {
-						boolean noPadding = beforeYearIdx == 0 && afterYearIdx + afterYear.length() == contentMatcher.start(); // allows fastpath return raw
-						String parsedYear = raw.substring(beforeYearIdx + beforeYear.length(), afterYearIdx);
-						if (parsedYear.equals(yearToday)) {
-							// it's good as is!
-							return noPadding ? raw : beforeYear + yearToday + afterYear + raw.substring(contentMatcher.start());
-						} else if (patternYearSingle.matcher(parsedYear).matches()) {
-							if (updateYearWithLatest) {
-								// expand from `2004` to `2004-2020`
-								return beforeYear + parsedYear + yearSepOrFull + yearToday + afterYear + raw.substring(contentMatcher.start());
-							} else {
-								// it's already good as a single year
-								return noPadding ? raw : beforeYear + parsedYear + afterYear + raw.substring(contentMatcher.start());
-							}
-						} else {
-							Matcher yearMatcher = patternYearSingle.matcher(parsedYear);
-							if (yearMatcher.find()) {
-								String firstYear = yearMatcher.group();
-								String newYear;
-								String secondYear;
-								if (updateYearWithLatest) {
-									secondYear = firstYear.equals(yearToday) ? null : yearToday;
-								} else if (yearMatcher.find(yearMatcher.end() + 1)) {
-									secondYear = yearMatcher.group();
-								} else {
-									secondYear = null;
-								}
-								if (secondYear == null) {
-									newYear = firstYear;
-								} else {
-									newYear = firstYear + yearSepOrFull + secondYear;
-								}
-								return noPadding && newYear.equals(parsedYear) ? raw : beforeYear + newYear + afterYear + raw.substring(contentMatcher.start());
+						// and also ends with exactly the right header, so it's easy to parse the existing year
+						String existingYear = raw.substring(beforeYearIdx + beforeYear.length(), afterYearIdx);
+						String newYear = calculateYearExact(existingYear);
+						if (existingYear.equals(newYear)) {
+							// fastpath where we don't need to make any changes at all
+							boolean noPadding = beforeYearIdx == 0 && afterYearIdx + afterYear.length() == contentMatcher.start(); // allows fastpath return raw
+							if (noPadding) {
+								return raw;
 							}
 						}
+						return beforeYear + newYear + afterYear + content;
+					} else {
+						String newYear = calculateYearBySearching(raw.substring(0, contentMatcher.start()));
+						// at worst, we just say that it was made today
+						return beforeYear + newYear + afterYear + content;
 					}
-					// at worst, we just say that it was made today
-					return beforeYear + yearToday + afterYear + raw.substring(contentMatcher.start());
 				}
 			}
 		}
 
+		private static final Pattern YYYY = Pattern.compile("[0-9]{4}");
+
+		/** Calculates the year to inject. */
+		private String calculateYearExact(String parsedYear) {
+			if (parsedYear.equals(yearToday)) {
+				return parsedYear;
+			} else if (YYYY.matcher(parsedYear).matches()) {
+				if (updateYearWithLatest) {
+					return parsedYear + yearSepOrFull + yearToday;
+				} else {
+					// it's already good as a single year
+					return parsedYear;
+				}
+			} else {
+				return calculateYearBySearching(parsedYear);
+			}
+		}
+
+		/** Searches the given string for YYYY, and uses that to determine the year range. */
+		private String calculateYearBySearching(String content) {
+			Matcher yearMatcher = YYYY.matcher(content);
+			if (yearMatcher.find()) {
+				String firstYear = yearMatcher.group();
+				String secondYear;
+				if (updateYearWithLatest) {
+					secondYear = firstYear.equals(yearToday) ? null : yearToday;
+				} else if (yearMatcher.find(yearMatcher.end() + 1)) {
+					secondYear = yearMatcher.group();
+				} else {
+					secondYear = null;
+				}
+				return secondYear == null ? firstYear : firstYear + yearSepOrFull + secondYear;
+			} else {
+				System.err.println("Can't parse copyright year '" + content + "', defaulting to " + yearToday);
+				// couldn't recognize the year format
+				return yearToday;
+			}
+		}
+
 		/** Sets copyright years on the given file by finding the oldest and most recent commits throughout git history. */
 		private String setLicenseHeaderYearsFromGitHistory(String raw, File file) throws IOException {
 			if (yearToday == null) {
diff --git a/plugin-gradle/CHANGES.md b/plugin-gradle/CHANGES.md
index e942ae1218..7d8f339840 100644
--- a/plugin-gradle/CHANGES.md
+++ b/plugin-gradle/CHANGES.md
@@ -3,6 +3,8 @@
 We adhere to the [keepachangelog](https://keepachangelog.com/en/1.0.0/) format (starting after version `3.27.0`).
 
 ## [Unreleased]
+### Changed
+* When applying license headers for the first time, we are now more lenient about parsing existing years from the header ([#690](https://github.com/diffplug/spotless/pull/690)).
 
 ## [5.4.0] - 2020-09-08
 ### Added
diff --git a/plugin-maven/CHANGES.md b/plugin-maven/CHANGES.md
index 951e0ea9a2..f435bb8911 100644
--- a/plugin-maven/CHANGES.md
+++ b/plugin-maven/CHANGES.md
@@ -3,6 +3,8 @@
 We adhere to the [keepachangelog](https://keepachangelog.com/en/1.0.0/) format (starting after version `1.27.0`).
 
 ## [Unreleased]
+### Changed
+* When applying license headers for the first time, we are now more lenient about parsing existing years from the header ([#690](https://github.com/diffplug/spotless/pull/690)).
 
 ## [2.2.0] - 2020-09-08
 ### Added
diff --git a/testlib/src/main/resources/license/FileWithLicenseHeaderAndPlaceholder.test b/testlib/src/main/resources/license/FileWithLicenseHeaderAndPlaceholder.test
deleted file mode 100644
index 3b43b9be2c..0000000000
--- a/testlib/src/main/resources/license/FileWithLicenseHeaderAndPlaceholder.test
+++ /dev/null
@@ -1,31 +0,0 @@
-/*
- * __LICENSE_PLACEHOLDER__
- **/
-package com.acme;
-
-import java.util.function.Function;
-
-
-public class Java8Test {
-    public void doStuff() throws Exception {
-        Function<String, Integer> example = Integer::parseInt;
-        example.andThen(val -> {
-            return val + 2;
-        } );
-        SimpleEnum val = SimpleEnum.A;
-        switch (val) {
-            case A:
-                break;
-            case B:
-                break;
-            case C:
-                break;
-            default:
-                throw new Exception();
-        }
-    }
-
-    public enum SimpleEnum {
-        A, B, C;
-    }
-}
diff --git a/testlib/src/main/resources/license/LicenseHeaderWithPlaceholder b/testlib/src/main/resources/license/LicenseHeaderWithPlaceholder
deleted file mode 100644
index fb22c11899..0000000000
--- a/testlib/src/main/resources/license/LicenseHeaderWithPlaceholder
+++ /dev/null
@@ -1,3 +0,0 @@
-/*
- * __LICENSE_PLACEHOLDER__
- **/
\ No newline at end of file
diff --git a/testlib/src/test/java/com/diffplug/spotless/generic/LicenseHeaderStepTest.java b/testlib/src/test/java/com/diffplug/spotless/generic/LicenseHeaderStepTest.java
index 9ca2f12245..85f44d8265 100644
--- a/testlib/src/test/java/com/diffplug/spotless/generic/LicenseHeaderStepTest.java
+++ b/testlib/src/test/java/com/diffplug/spotless/generic/LicenseHeaderStepTest.java
@@ -29,108 +29,108 @@
 import com.diffplug.spotless.generic.LicenseHeaderStep.YearMode;
 
 public class LicenseHeaderStepTest extends ResourceHarness {
-	private static final String KEY_LICENSE = "license/TestLicense";
-	private static final String KEY_FILE_NOTAPPLIED = "license/MissingLicense.test";
-	private static final String KEY_FILE_APPLIED = "license/HasLicense.test";
-
-	private static final String KEY_FILE_WITHOUT_LICENSE = "license/FileWithoutLicenseHeader.test";
-	// Templates to test with custom license contents
-	private static final String KEY_LICENSE_WITH_PLACEHOLDER = "license/LicenseHeaderWithPlaceholder";
-	private static final String KEY_FILE_WITH_LICENSE_AND_PLACEHOLDER = "license/FileWithLicenseHeaderAndPlaceholder.test";
-	// Licenses to test $YEAR token replacement
-	private static final String HEADER_WITH_YEAR = "This is a fake license, $YEAR. ACME corp.";
-	// License to test $today.year token replacement
-	private static final String HEADER_WITH_YEAR_INTELLIJ = "This is a fake license, $today.year. ACME corp.";
-	// Special case where the characters immediately before and after the year token are the same,
-	// start position of the second part might overlap the end position of the first part.
-	private static final String HEADER_WITH_YEAR_VARIANT = "This is a fake license. Copyright $YEAR ACME corp.";
-
-	// If this constant changes, don't forget to change the similarly-named one in
-	// plugin-gradle/src/main/java/com/diffplug/gradle/spotless/JavaExtension.java as well
-	private static final String LICENSE_HEADER_DELIMITER = "package ";
+	private static final String FILE_NO_LICENSE = "license/FileWithoutLicenseHeader.test";
+	private static final String package_ = "package ";
+	private static final String HEADER_WITH_$YEAR = "This is a fake license, $YEAR. ACME corp.";
+
+	@Test
+	public void parseExistingYear() throws Exception {
+		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(header(HEADER_WITH_$YEAR), package_).build())
+				// has existing
+				.test(hasHeader("This is a fake license, 2007. ACME corp."), hasHeader("This is a fake license, 2007. ACME corp."))
+				// if prefix changes, the year will get set to today
+				.test(hasHeader("This is a license, 2007. ACME corp."), hasHeader("This is a fake license, 2007. ACME corp."))
+				// if suffix changes, the year will get set to today
+				.test(hasHeader("This is a fake license, 2007. Other corp."), hasHeader("This is a fake license, 2007. ACME corp."));
+	}
 
 	@Test
 	public void fromHeader() throws Throwable {
-		FormatterStep step = LicenseHeaderStep.headerDelimiter(getTestResource(KEY_LICENSE), LICENSE_HEADER_DELIMITER).build();
-		assertOnResources(step, KEY_FILE_NOTAPPLIED, KEY_FILE_APPLIED);
+		FormatterStep step = LicenseHeaderStep.headerDelimiter(getTestResource("license/TestLicense"), package_).build();
+		StepHarness.forStep(step)
+				.testResource("license/MissingLicense.test", "license/HasLicense.test");
 	}
 
 	@Test
 	public void should_apply_license_containing_YEAR_token() throws Throwable {
-		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(licenseWith(HEADER_WITH_YEAR), LICENSE_HEADER_DELIMITER).build())
-				.test(getTestResource(KEY_FILE_WITHOUT_LICENSE), fileContainingYear(HEADER_WITH_YEAR, currentYear()))
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, currentYear()))
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, "2003"))
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, "1990-2015"))
-				.test(fileContainingYear("Something before license.*/\n/* \n * " + HEADER_WITH_YEAR, "2003"), fileContainingYear(HEADER_WITH_YEAR, currentYear()))
-				.test(fileContainingYear(HEADER_WITH_YEAR + "\n **/\n/* Something after license.", "2003"), fileContainingYear(HEADER_WITH_YEAR, "2003"))
-				.test(fileContainingYear(HEADER_WITH_YEAR, "not a year"), fileContainingYear(HEADER_WITH_YEAR, currentYear()));
+		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(header(HEADER_WITH_$YEAR), package_).build())
+				.test(getTestResource(FILE_NO_LICENSE), hasHeaderYear(currentYear()))
+				.testUnaffected(hasHeaderYear(currentYear()))
+				.testUnaffected(hasHeaderYear("2003"))
+				.testUnaffected(hasHeaderYear("1990-2015"))
+				.test(hasHeaderYear("Something before license.*/\n/* \n * " + HEADER_WITH_$YEAR, "2003"), hasHeaderYear("2003"))
+				.test(hasHeaderYear(HEADER_WITH_$YEAR + "\n **/\n/* Something after license.", "2003"), hasHeaderYear("2003"))
+				.test(hasHeaderYear("not a year"), hasHeaderYear(currentYear()));
 		// Check with variant
-		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(licenseWith(HEADER_WITH_YEAR_VARIANT), LICENSE_HEADER_DELIMITER).build())
-				.test(getTestResource(KEY_FILE_WITHOUT_LICENSE), fileContainingYear(HEADER_WITH_YEAR_VARIANT, currentYear()))
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR_VARIANT, currentYear()))
-				.test(fileContaining("This is a fake license. Copyright "), fileContainingYear(HEADER_WITH_YEAR_VARIANT, currentYear()))
-				.test(fileContaining(" ACME corp."), fileContainingYear(HEADER_WITH_YEAR_VARIANT, currentYear()))
-				.test(fileContaining("This is a fake license. Copyright ACME corp."), fileContainingYear(HEADER_WITH_YEAR_VARIANT, currentYear()))
-				.test(fileContaining("This is a fake license. CopyrightACME corp."), fileContainingYear(HEADER_WITH_YEAR_VARIANT, currentYear()));
+		String otherFakeLicense = "This is a fake license. Copyright $YEAR ACME corp.";
+		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(header(otherFakeLicense), package_).build())
+				.test(getTestResource(FILE_NO_LICENSE), hasHeaderYear(otherFakeLicense, currentYear()))
+				.testUnaffected(hasHeaderYear(otherFakeLicense, currentYear()))
+				.test(hasHeader("This is a fake license. Copyright "), hasHeaderYear(otherFakeLicense, currentYear()))
+				.test(hasHeader(" ACME corp."), hasHeaderYear(otherFakeLicense, currentYear()))
+				.test(hasHeader("This is a fake license. Copyright ACME corp."), hasHeaderYear(otherFakeLicense, currentYear()))
+				.test(hasHeader("This is a fake license. CopyrightACME corp."), hasHeaderYear(otherFakeLicense, currentYear()));
 
 		//Check when token is of the format $today.year
-		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(licenseWith(HEADER_WITH_YEAR_INTELLIJ), LICENSE_HEADER_DELIMITER).build())
-				.test(fileContaining(HEADER_WITH_YEAR_INTELLIJ), fileWithLicenseContaining(HEADER_WITH_YEAR_INTELLIJ, currentYear(), "$today.year"));
-	}
-
-	private String fileWithLicenseContaining(String license, String yearContent, String token) throws IOException {
-		return getTestResource(KEY_FILE_WITH_LICENSE_AND_PLACEHOLDER).replace("__LICENSE_PLACEHOLDER__", license).replace(token, yearContent);
+		String HEADER_WITH_YEAR_INTELLIJ = "This is a fake license, $today.year. ACME corp.";
+		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(header(HEADER_WITH_YEAR_INTELLIJ), package_).build())
+				.test(hasHeader(HEADER_WITH_YEAR_INTELLIJ), hasHeader(HEADER_WITH_YEAR_INTELLIJ.replace("$today.year", currentYear())));
 	}
 
 	@Test
 	public void updateYearWithLatest() throws Throwable {
-		FormatterStep step = LicenseHeaderStep.headerDelimiter(licenseWith(HEADER_WITH_YEAR), LICENSE_HEADER_DELIMITER)
+		FormatterStep step = LicenseHeaderStep.headerDelimiter(header(HEADER_WITH_$YEAR), package_)
 				.withYearMode(YearMode.UPDATE_TO_TODAY)
 				.build();
 		StepHarness.forStep(step)
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, currentYear()))
-				.test(fileContainingYear(HEADER_WITH_YEAR, "2003"), fileContainingYear(HEADER_WITH_YEAR, "2003-" + currentYear()))
-				.test(fileContainingYear(HEADER_WITH_YEAR, "1990-2015"), fileContainingYear(HEADER_WITH_YEAR, "1990-" + currentYear()));
+				.testUnaffected(hasHeaderYear(currentYear()))
+				.test(hasHeaderYear("2003"), hasHeaderYear("2003-" + currentYear()))
+				.test(hasHeaderYear("1990-2015"), hasHeaderYear("1990-" + currentYear()));
 	}
 
 	@Test
 	public void should_apply_license_containing_YEAR_token_with_non_default_year_separator() throws Throwable {
-		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(licenseWith(HEADER_WITH_YEAR), LICENSE_HEADER_DELIMITER).withYearSeparator(", ").build())
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, "1990, 2015"))
-				.test(fileContainingYear(HEADER_WITH_YEAR, "1990-2015"), fileContainingYear(HEADER_WITH_YEAR, "1990, 2015"));
+		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(header(HEADER_WITH_$YEAR), package_).withYearSeparator(", ").build())
+				.testUnaffected(hasHeaderYear("1990, 2015"))
+				.test(hasHeaderYear("1990-2015"), hasHeaderYear("1990, 2015"));
 	}
 
 	@Test
 	public void should_apply_license_containing_YEAR_token_with_special_character_in_year_separator() throws Throwable {
-		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(licenseWith(HEADER_WITH_YEAR), LICENSE_HEADER_DELIMITER).withYearSeparator("(").build())
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, "1990(2015"))
-				.test(fileContainingYear(HEADER_WITH_YEAR, "1990-2015"), fileContainingYear(HEADER_WITH_YEAR, "1990(2015"));
+		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(header(HEADER_WITH_$YEAR), package_).withYearSeparator("(").build())
+				.testUnaffected(hasHeaderYear("1990(2015"))
+				.test(hasHeaderYear("1990-2015"), hasHeaderYear("1990(2015"));
 	}
 
 	@Test
 	public void should_apply_license_containing_YEAR_token_with_custom_separator() throws Throwable {
-		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(licenseWith(HEADER_WITH_YEAR), LICENSE_HEADER_DELIMITER).build())
-				.test(getTestResource(KEY_FILE_WITHOUT_LICENSE), fileContainingYear(HEADER_WITH_YEAR, currentYear()))
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, currentYear()))
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, "2003"))
-				.testUnaffected(fileContainingYear(HEADER_WITH_YEAR, "1990-2015"))
-				.test(fileContainingYear(HEADER_WITH_YEAR, "not a year"), fileContainingYear(HEADER_WITH_YEAR, currentYear()));
+		StepHarness.forStep(LicenseHeaderStep.headerDelimiter(header(HEADER_WITH_$YEAR), package_).build())
+				.test(getTestResource(FILE_NO_LICENSE), hasHeaderYear(currentYear()))
+				.testUnaffected(hasHeaderYear(currentYear()))
+				.testUnaffected(hasHeaderYear("2003"))
+				.testUnaffected(hasHeaderYear("1990-2015"))
+				.test(hasHeaderYear("not a year"), hasHeaderYear(currentYear()));
+	}
+
+	private String header(String contents) throws IOException {
+		return "/*\n" +
+				" * " + contents + "\n" +
+				" **/\n";
 	}
 
-	private String licenseWith(String contents) throws IOException {
-		return getTestResource(KEY_LICENSE_WITH_PLACEHOLDER).replace("__LICENSE_PLACEHOLDER__", contents);
+	private String hasHeader(String header) throws IOException {
+		return header(header) + getTestResource(FILE_NO_LICENSE);
 	}
 
-	private String fileContaining(String license) throws IOException {
-		return fileContainingYear(license, "");
+	private String hasHeaderYear(String license, String years) throws IOException {
+		return header(license).replace("$YEAR", years) + getTestResource(FILE_NO_LICENSE);
 	}
 
-	private String fileContainingYear(String license, String yearContent) throws IOException {
-		return getTestResource(KEY_FILE_WITH_LICENSE_AND_PLACEHOLDER).replace("__LICENSE_PLACEHOLDER__", license).replace("$YEAR", yearContent);
+	private String hasHeaderYear(String years) throws IOException {
+		return hasHeaderYear(HEADER_WITH_$YEAR, years);
 	}
 
-	private String currentYear() {
+	private static String currentYear() {
 		return String.valueOf(YearMonth.now().getYear());
 	}