diff --git a/server/api/helpers/attachments/process-uploaded-file.js b/server/api/helpers/attachments/process-uploaded-file.js
index 4d66bf0c..61defb7b 100644
--- a/server/api/helpers/attachments/process-uploaded-file.js
+++ b/server/api/helpers/attachments/process-uploaded-file.js
@@ -47,13 +47,20 @@ module.exports = {
       fs.mkdirSync(thumbnailsPath);
 
       const { width, pageHeight: height = metadata.height } = metadata;
+      const isPortrait = height > width;
       const thumbnailsExtension = metadata.format === 'jpeg' ? 'jpg' : metadata.format;
 
       try {
         await image
-          .resize(256, height > width ? 320 : undefined, {
-            kernel: sharp.kernel.nearest,
-          })
+          .resize(
+            256,
+            isPortrait ? 320 : undefined,
+            width < 256 || (isPortrait && height < 320)
+              ? {
+                  kernel: sharp.kernel.nearest,
+                }
+              : undefined,
+          )
           .toFile(path.join(thumbnailsPath, `cover-256.${thumbnailsExtension}`));
 
         fileData.image = {
diff --git a/server/api/helpers/projects/process-uploaded-background-image-file.js b/server/api/helpers/projects/process-uploaded-background-image-file.js
index 39c8e922..ebec3e4f 100644
--- a/server/api/helpers/projects/process-uploaded-background-image-file.js
+++ b/server/api/helpers/projects/process-uploaded-background-image-file.js
@@ -37,15 +37,22 @@ module.exports = {
 
     fs.mkdirSync(rootPath);
 
+    const { width, pageHeight: height = metadata.height } = metadata;
     const extension = metadata.format === 'jpeg' ? 'jpg' : metadata.format;
 
     try {
       await image.toFile(path.join(rootPath, `original.${extension}`));
 
       await image
-        .resize(336, 200, {
-          kernel: sharp.kernel.nearest,
-        })
+        .resize(
+          336,
+          200,
+          width < 336 || height < 200
+            ? {
+                kernel: sharp.kernel.nearest,
+              }
+            : undefined,
+        )
         .toFile(path.join(rootPath, `cover-336.${extension}`));
     } catch (error1) {
       try {
diff --git a/server/api/helpers/users/process-uploaded-avatar-file.js b/server/api/helpers/users/process-uploaded-avatar-file.js
index 5cbc5018..40300573 100644
--- a/server/api/helpers/users/process-uploaded-avatar-file.js
+++ b/server/api/helpers/users/process-uploaded-avatar-file.js
@@ -37,15 +37,22 @@ module.exports = {
 
     fs.mkdirSync(rootPath);
 
+    const { width, pageHeight: height = metadata.height } = metadata;
     const extension = metadata.format === 'jpeg' ? 'jpg' : metadata.format;
 
     try {
       await image.toFile(path.join(rootPath, `original.${extension}`));
 
       await image
-        .resize(100, 100, {
-          kernel: sharp.kernel.nearest,
-        })
+        .resize(
+          100,
+          100,
+          width < 100 || height < 100
+            ? {
+                kernel: sharp.kernel.nearest,
+              }
+            : undefined,
+        )
         .toFile(path.join(rootPath, `square-100.${extension}`));
     } catch (error1) {
       try {
diff --git a/server/db/migrations/20221226210239_improve_quality_of_resized_images.js b/server/db/migrations/20221226210239_improve_quality_of_resized_images.js
new file mode 100644
index 00000000..ffc40cd6
--- /dev/null
+++ b/server/db/migrations/20221226210239_improve_quality_of_resized_images.js
@@ -0,0 +1,129 @@
+const path = require('path');
+const sharp = require('sharp');
+
+const getConfig = require('../../get-config');
+
+const processUserAvatar = async (user, userAvatarsPath) => {
+  const rootPath = path.join(userAvatarsPath, user.avatar.dirname);
+
+  const image = sharp(path.join(rootPath, `original.${user.avatar.extension}`), {
+    animated: true,
+  });
+
+  let metadata;
+  try {
+    metadata = await image.metadata();
+  } catch (error) {
+    return;
+  }
+
+  const { width, pageHeight: height = metadata.height } = metadata;
+
+  try {
+    await image
+      .resize(
+        100,
+        100,
+        width < 100 || height < 100
+          ? {
+              kernel: sharp.kernel.nearest,
+            }
+          : undefined,
+      )
+      .toFile(path.join(rootPath, `square-100.${user.avatar.extension}`));
+  } catch (error) {} // eslint-disable-line no-empty
+};
+
+const processProjectBackgroundImage = async (project, projectBackgroundImagesPath) => {
+  const rootPath = path.join(projectBackgroundImagesPath, project.background_image.dirname);
+
+  const image = sharp(path.join(rootPath, `original.${project.background_image.extension}`), {
+    animated: true,
+  });
+
+  let metadata;
+  try {
+    metadata = await image.metadata();
+  } catch (error) {
+    return;
+  }
+
+  const { width, pageHeight: height = metadata.height } = metadata;
+
+  try {
+    await image
+      .resize(
+        336,
+        200,
+        width < 336 || height < 200
+          ? {
+              kernel: sharp.kernel.nearest,
+            }
+          : undefined,
+      )
+      .toFile(path.join(rootPath, `cover-336.${project.background_image.extension}`));
+  } catch (error) {} // eslint-disable-line no-empty
+};
+
+const processAttachmentImage = async (attachment, attachmentsPath) => {
+  const rootPath = path.join(attachmentsPath, attachment.dirname);
+  const thumbnailsPath = path.join(rootPath, 'thumbnails');
+
+  const image = sharp(path.join(rootPath, attachment.filename), {
+    animated: true,
+  });
+
+  let metadata;
+  try {
+    metadata = await image.metadata();
+  } catch (error) {
+    return;
+  }
+
+  const { width, pageHeight: height = metadata.height } = metadata;
+  const isPortrait = height > width;
+
+  try {
+    await image
+      .resize(
+        256,
+        isPortrait ? 320 : undefined,
+        width < 256 || (isPortrait && height < 320)
+          ? {
+              kernel: sharp.kernel.nearest,
+            }
+          : undefined,
+      )
+      .toFile(path.join(thumbnailsPath, `cover-256.${attachment.image.thumbnailsExtension}`));
+  } catch (error) {} // eslint-disable-line no-empty
+};
+
+module.exports.up = async (knex) => {
+  const config = await getConfig();
+
+  const users = await knex('user_account').whereNotNull('avatar');
+
+  // eslint-disable-next-line no-restricted-syntax
+  for (user of users) {
+    // eslint-disable-next-line no-await-in-loop
+    await processUserAvatar(user, config.custom.userAvatarsPath);
+  }
+
+  const projects = await knex('project').whereNotNull('background_image');
+
+  // eslint-disable-next-line no-restricted-syntax
+  for (project of projects) {
+    // eslint-disable-next-line no-await-in-loop
+    await processProjectBackgroundImage(project, config.custom.projectBackgroundImagesPath);
+  }
+
+  const attachments = await knex('attachment').whereNotNull('image');
+
+  // eslint-disable-next-line no-restricted-syntax
+  for (attachment of attachments) {
+    // eslint-disable-next-line no-await-in-loop
+    await processAttachmentImage(attachment, config.custom.attachmentsPath);
+  }
+};
+
+module.exports.down = () => Promise.resolve();