diff --git a/core/server/adapters/storage/LocalFileStorage.js b/core/server/adapters/storage/LocalFileStorage.js
index da46eb9d09..71d2af0f65 100644
--- a/core/server/adapters/storage/LocalFileStorage.js
+++ b/core/server/adapters/storage/LocalFileStorage.js
@@ -19,6 +19,31 @@ class LocalFileStore extends StorageBase {
         this.storagePath = config.getContentPath('images');
     }
 
+    /**
+     * Saves a buffer in the targetPath
+     * - buffer is an instance of Buffer
+     * - returns a Promise which returns the full URL to retrieve the data
+     */
+    saveRaw(buffer, targetPath) {
+        const storagePath = path.join(this.storagePath, targetPath);
+        const targetDir = path.dirname(storagePath);
+
+        return fs.mkdirs(targetDir)
+            .then(() => {
+                return fs.writeFile(storagePath, buffer);
+            })
+            .then(() => {
+                // For local file system storage can use relative path so add a slash
+                const fullUrl = (
+                    urlService.utils.urlJoin('/', urlService.utils.getSubdir(),
+                        urlService.utils.STATIC_IMAGE_URL_PREFIX,
+                        targetPath)
+                ).replace(new RegExp(`\\${path.sep}`, 'g'), '/');
+
+                return fullUrl;
+            });
+    }
+
     /**
      * Saves the image to storage (the file system)
      * - image is the express image object
diff --git a/core/server/lib/image/manipulator.js b/core/server/lib/image/manipulator.js
index 2da4b93fd4..9051272d7b 100644
--- a/core/server/lib/image/manipulator.js
+++ b/core/server/lib/image/manipulator.js
@@ -61,4 +61,27 @@ const process = (options = {}) => {
         });
 };
 
+const resizeImage = (originalBuffer, {width, height} = {}) => {
+    const sharp = require('sharp');
+    return sharp(originalBuffer)
+        .resize(width, height, {
+            // CASE: dont make the image bigger than it was
+            withoutEnlargement: true
+        })
+        // CASE: Automatically remove metadata and rotate based on the orientation.
+        .rotate()
+        .toBuffer()
+        .then((resizedBuffer) => {
+            return resizedBuffer.length < originalBuffer.length ? resizedBuffer : originalBuffer;
+        });
+};
+
 module.exports.process = process;
+module.exports.safeResizeImage = (buffer, options) => {
+    try {
+        require('sharp');
+        return resizeImage(buffer, options);
+    } catch (e) {
+        return Promise.resolve(buffer);
+    }
+};
diff --git a/core/server/web/shared/middlewares/image/handle-image-sizes.js b/core/server/web/shared/middlewares/image/handle-image-sizes.js
new file mode 100644
index 0000000000..169c3e8f73
--- /dev/null
+++ b/core/server/web/shared/middlewares/image/handle-image-sizes.js
@@ -0,0 +1,62 @@
+const path = require('path');
+const image = require('../../../../lib/image');
+const storage = require('../../../../adapters/storage');
+const activeTheme = require('../../../../services/themes/active');
+
+const SIZE_PATH_REGEX = /^\/size\/([^/]+)\//;
+
+module.exports = function (req, res, next) {
+    if (!SIZE_PATH_REGEX.test(req.url)) {
+        return next();
+    }
+
+    const [sizeImageDir, requestedDimension] = req.url.match(SIZE_PATH_REGEX);
+    const redirectToOriginal = () => {
+        const url = req.originalUrl.replace(`/size/${requestedDimension}`, '');
+        return res.redirect(url);
+    };
+
+    const imageSizes = activeTheme.get().config('image_sizes');
+    // CASE: no image_sizes config
+    if (!imageSizes) {
+        return redirectToOriginal();
+    }
+
+    const imageDimensions = Object.keys(imageSizes).reduce((dimensions, size) => {
+        const {width, height} = imageSizes[size];
+        const dimension = (width ? 'w' + width : '') + (height ? 'h' + height : '');
+        return Object.assign({
+            [dimension]: imageSizes[size]
+        }, dimensions);
+    }, {});
+
+    const imageDimensionConfig = imageDimensions[requestedDimension];
+    // CASE: unknown dimension
+    if (!imageDimensionConfig || (!imageDimensionConfig.width && !imageDimensionConfig.height)) {
+        return redirectToOriginal();
+    }
+
+    const storageInstance = storage.getStorage();
+    // CASE: unsupported storage adapter but theme is using custom image_sizes
+    if (typeof storageInstance.saveRaw !== 'function') {
+        return redirectToOriginal();
+    }
+
+    storageInstance.exists(req.url).then((exists) => {
+        if (exists) {
+            return;
+        }
+
+        const originalImagePath = path.relative(sizeImageDir, req.url);
+
+        return storageInstance.read({path: originalImagePath})
+            .then((originalImageBuffer) => {
+                return image.manipulator.safeResizeImage(originalImageBuffer, imageDimensionConfig);
+            })
+            .then((resizedImageBuffer) => {
+                return storageInstance.saveRaw(resizedImageBuffer, req.url);
+            });
+    }).then(() => {
+        next();
+    }).catch(next);
+};
diff --git a/core/server/web/shared/middlewares/image/index.js b/core/server/web/shared/middlewares/image/index.js
index f5bb85b7f3..df419227b5 100644
--- a/core/server/web/shared/middlewares/image/index.js
+++ b/core/server/web/shared/middlewares/image/index.js
@@ -1,5 +1,8 @@
 module.exports = {
     get normalize() {
         return require('./normalize');
+    },
+    get handleImageSizes() {
+        return require('./handle-image-sizes');
     }
 };
diff --git a/core/server/web/site/app.js b/core/server/web/site/app.js
index 41ac6a2024..43ba05bb0f 100644
--- a/core/server/web/site/app.js
+++ b/core/server/web/site/app.js
@@ -13,6 +13,8 @@ const themeMiddleware = require('../../services/themes').middleware;
 const siteRoutes = require('./routes');
 const shared = require('../shared');
 
+const STATIC_IMAGE_URL_PREFIX = `/${urlService.utils.STATIC_IMAGE_URL_PREFIX}`;
+
 let router;
 
 function SiteRouter(req, res, next) {
@@ -58,7 +60,7 @@ module.exports = function setupSiteApp(options = {}) {
     siteApp.use(shared.middlewares.servePublicFile('public/404-ghost.png', 'png', constants.ONE_HOUR_S));
 
     // Serve blog images using the storage adapter
-    siteApp.use('/' + urlService.utils.STATIC_IMAGE_URL_PREFIX, storage.getStorage().serve());
+    siteApp.use(STATIC_IMAGE_URL_PREFIX, shared.middlewares.image.handleImageSizes, storage.getStorage().serve());
 
     // @TODO find this a better home
     // We do this here, at the top level, because helpers require so much stuff.
diff --git a/core/test/unit/web/middleware/image/handle-image-sizes_spec.js b/core/test/unit/web/middleware/image/handle-image-sizes_spec.js
new file mode 100644
index 0000000000..60c46f3bb2
--- /dev/null
+++ b/core/test/unit/web/middleware/image/handle-image-sizes_spec.js
@@ -0,0 +1,44 @@
+const should = require('should');
+const handleImageSizes = require('../../../../../server/web/shared/middlewares/image/handle-image-sizes.js');
+
+// @TODO make these tests lovely and non specific to implementation
+describe('handleImageSizes middleware', function () {
+    it('calls next immediately if the url does not match /size/something/', function (done) {
+        const fakeReq = {
+            url: '/size/something'
+        };
+        // CASE: second thing middleware does is try to match to a regex
+        fakeReq.url.match = function () {
+            throw new Error('Should have exited immediately');
+        };
+        handleImageSizes(fakeReq, {}, function next() {
+            done();
+        });
+    });
+
+    it('calls next immediately if the url does not match /size/something/', function (done) {
+        const fakeReq = {
+            url: '/url/whatever/'
+        };
+        // CASE: second thing middleware does is try to match to a regex
+        fakeReq.url.match = function () {
+            throw new Error('Should have exited immediately');
+        };
+        handleImageSizes(fakeReq, {}, function next() {
+            done();
+        });
+    });
+
+    it('calls next immediately if the url does not match /size/something/', function (done) {
+        const fakeReq = {
+            url: '/size//'
+        };
+        // CASE: second thing middleware does is try to match to a regex
+        fakeReq.url.match = function () {
+            throw new Error('Should have exited immediately');
+        };
+        handleImageSizes(fakeReq, {}, function next() {
+            done();
+        });
+    });
+});