diff --git a/docs/changelog.md b/docs/changelog.md
index 23c1b34a..5c3c3f3c 100644
--- a/docs/changelog.md
+++ b/docs/changelog.md
@@ -14,6 +14,9 @@ Requires libvips v8.14.3
   [#3755](https://github.com/lovell/sharp/pull/3755)
   [@kleisauke](https://github.com/kleisauke)
 
+* Ensure resize with a `fit` of `inside` respects 90/270 degree rotation.
+  [#3756](https://github.com/lovell/sharp/issues/3756)
+
 * TypeScript: Ensure `minSize` property of `WebpOptions` is boolean.
   [#3758](https://github.com/lovell/sharp/pull/3758)
   [@sho-xizz](https://github.com/sho-xizz)
diff --git a/src/common.cc b/src/common.cc
index 075c6008..54354edb 100644
--- a/src/common.cc
+++ b/src/common.cc
@@ -968,6 +968,9 @@ namespace sharp {
     if (swap && canvas != Canvas::IGNORE_ASPECT) {
       // Swap input width and height when requested.
       std::swap(width, height);
+      if (canvas == Canvas::MAX) {
+        std::swap(targetWidth, targetHeight);
+      }
     }
 
     double hshrink = 1.0;
diff --git a/test/unit/rotate.js b/test/unit/rotate.js
index 86e9a8a6..b5758082 100644
--- a/test/unit/rotate.js
+++ b/test/unit/rotate.js
@@ -489,4 +489,28 @@ describe('Rotation', function () {
       .timeout({ seconds: 5 })
       .toBuffer()
   );
+
+  it('Rotate 90 then resize with inside fit', async () => {
+    const data = await sharp({ create: { width: 16, height: 8, channels: 3, background: 'red' } })
+      .rotate(90)
+      .resize({ width: 6, fit: 'inside' })
+      .png({ compressionLevel: 0 })
+      .toBuffer();
+
+    const { width, height } = await sharp(data).metadata();
+    assert.strictEqual(width, 6);
+    assert.strictEqual(height, 12);
+  });
+
+  it('Resize with inside fit then rotate 90', async () => {
+    const data = await sharp({ create: { width: 16, height: 8, channels: 3, background: 'red' } })
+      .resize({ width: 6, fit: 'inside' })
+      .rotate(90)
+      .png({ compressionLevel: 0 })
+      .toBuffer();
+
+    const { width, height } = await sharp(data).metadata();
+    assert.strictEqual(width, 3);
+    assert.strictEqual(height, 6);
+  });
 });