diff --git a/src/prepare.test.ts b/src/prepare.test.ts
index 289a89e..6b45e11 100644
--- a/src/prepare.test.ts
+++ b/src/prepare.test.ts
@@ -32,6 +32,7 @@ describe('prepare', function () {
       );
       const [, newChangelog] = mocks.writeFileSync.mock.lastCall;
       expect(newChangelog).to.eq(`# A Totally ficticious Changelog
+
 ## v1.0.0
 
 thing v1.0.0 (major)
@@ -46,4 +47,36 @@ thing v1.0.0 (major)
 `);
     });
   });
+
+  it('updates changelog correctly with case insensitive CHANGELOG', function () {
+    mocks.readFileSync.mockReturnValue(`# A Totally ficticious CHANGELOG
+
+## Some Old version
+
+- added some features
+- spent a lot of time trying to figure out releases (if only there was a tool to help with that)
+`);
+    updateChangelog(
+      `## v1.0.0
+
+- added release-plan (how did I live without it!?)
+- releasing initial working version`,
+      new Map([['thing', { newVersion: 'v1.0.0', impact: 'major' }]]) as any,
+    );
+    const [, newChangelog] = mocks.writeFileSync.mock.lastCall;
+    expect(newChangelog).to.eq(`# A Totally ficticious CHANGELOG
+
+## v1.0.0
+
+thing v1.0.0 (major)
+
+- added release-plan (how did I live without it!?)
+- releasing initial working version
+
+## Some Old version
+
+- added some features
+- spent a lot of time trying to figure out releases (if only there was a tool to help with that)
+`);
+  });
 });
diff --git a/src/prepare.ts b/src/prepare.ts
index 2600ba7..277f9b7 100644
--- a/src/prepare.ts
+++ b/src/prepare.ts
@@ -6,7 +6,7 @@ import fsExtra from 'fs-extra';
 
 const { readJSONSync, writeJSONSync } = fsExtra;
 
-const changelogPreamblePattern = /#.*Changelog.*$/;
+const changelogPreamblePattern = /#.*Changelog.*$/i;
 
 export function updateChangelog(
   newChangelogContent: string,
@@ -38,7 +38,7 @@ export function updateChangelog(
   writeFileSync(
     targetChangelogFile,
     oldChangelogContent[0] +
-      '\n' +
+      '\n\n' +
       newOutput +
       oldChangelogContent.slice(1).join('\n'),
   );