diff --git a/ghost/external-media-inliner/lib/ExternalMediaInliner.js b/ghost/external-media-inliner/lib/ExternalMediaInliner.js
index 14546e7051..4fb5ff69d7 100644
--- a/ghost/external-media-inliner/lib/ExternalMediaInliner.js
+++ b/ghost/external-media-inliner/lib/ExternalMediaInliner.js
@@ -1,7 +1,9 @@
 const mime = require('mime-types');
+const FileType = require('file-type');
 const request = require('@tryghost/request');
 const errors = require('@tryghost/errors');
 const logging = require('@tryghost/logging');
+const string = require('@tryghost/string');
 const path = require('path');
 
 class ExternalMediaInliner {
@@ -39,14 +41,22 @@ class ExternalMediaInliner {
      * @param {string} requestURL - url of remote media
      * @returns {Promise<Object>}
      */
-    async #getRemoteMedia(requestURL) {
+    async getRemoteMedia(requestURL) {
         // @NOTE: this is the most expensive operation in the whole inlining process
         //        we should consider caching the results to improve performance
+
+        // Enforce http - http > https redirects are commonplace
+        requestURL = requestURL.replace(/^\/\//g, 'http://');
+
+        // Encode to handle special characters in URLs
+        requestURL = encodeURI(requestURL);
         try {
-            return await request(requestURL, {
+            const response = await request(requestURL, {
                 followRedirect: true,
                 responseType: 'buffer'
             });
+
+            return response;
         } catch (error) {
             // NOTE: add special case for 404s
             logging.error(`Error downloading remote media: ${requestURL}`);
@@ -63,21 +73,34 @@ class ExternalMediaInliner {
      * @param {Object} response - response from request
      * @returns {Object}
      */
-    #extractFileDataFromResponse(requestURL, response) {
-        const headers = response.headers;
-        const contentType = headers['content-type'];
+    async extractFileDataFromResponse(requestURL, response) {
+        let extension;
 
-        const filename = requestURL
-            .split('/')
-            .pop()
-            .split('#')[0]
-            .split('?')[0];
+        // Attempt to get the file extension from the file itself
+        // If that fails, or if `.ext` is undefined, get the extension from the file path in the catch
+        try {
+            const fileInfo = await FileType.fromBuffer(response.body);
+            extension = fileInfo.ext;
+        } catch {
+            const headers = response.headers;
+            const contentType = headers['content-type'];
+            const extensionFromPath = path.parse(requestURL).ext.split(/[^a-z]/i).filter(Boolean)[0];
+            extension = mime.extension(contentType) || extensionFromPath;
+        }
 
-        const extension = mime.extension(contentType) || filename.split('.').pop();
+        const removeExtRegExp = new RegExp(`.${extension}`, '');
+        const fileNameNoExt = path.parse(requestURL).base.replace(removeExtRegExp, '');
+
+        // CASE: Query strings _can_ form part of the unique image URL, so rather that strip them include the in the file name
+        // Then trim to last 248 chars (this will be more unique than the first 248), and trim leading & trailing dashes.
+        // 248 is on the lower end of limits from various OSes and file systems
+        const fileName = string.slugify(path.parse(fileNameNoExt).base, {
+            requiredChangesOnly: true
+        }).slice(-248).replace(/^-|-$/, '');
 
         return {
             fileBuffer: response.body,
-            filename: filename,
+            filename: `${fileName}.${extension}`,
             extension: `.${extension}`
         };
     }
@@ -87,7 +110,7 @@ class ExternalMediaInliner {
      * @param {Object} media - media to store locally
      * @returns {Promise<string>} - path to stored media
      */
-    async #storeMediaLocally(media) {
+    async storeMediaLocally(media) {
         const storage = this.getMediaStorage(media.extension);
 
         if (!storage) {
@@ -106,7 +129,7 @@ class ExternalMediaInliner {
         }
     }
 
-    async #inlineMibiledoc(mobiledoc, domains) {
+    async inlineMobiledoc(mobiledoc, domains) {
         for (const domain of domains) {
             // NOTE: the src could end with a quote, apostrophe or double-backslash. backlashes are added to mobiledoc
             //       as an escape character
@@ -115,15 +138,15 @@ class ExternalMediaInliner {
             const matches = mobiledoc.matchAll(regex);
 
             for (const [,src] of matches) {
-                const response = await this.#getRemoteMedia(src);
+                const response = await this.getRemoteMedia(src);
 
                 let media;
                 if (response) {
-                    media = this.#extractFileDataFromResponse(src, response);
+                    media = await this.extractFileDataFromResponse(src, response);
                 }
 
                 if (media) {
-                    const filePath = await this.#storeMediaLocally(media);
+                    const filePath = await this.storeMediaLocally(media);
 
                     if (filePath) {
                         const inlinedSrc = `__GHOST_URL__${filePath}`;
@@ -147,7 +170,7 @@ class ExternalMediaInliner {
      * @param {String[]} domains - domains to inline media from
      * @returns Promise<Object> - updated fields map with local media paths
      */
-    async #inlineFields(resourceModel, fields, domains) {
+    async inlineFields(resourceModel, fields, domains) {
         const updatedFields = {};
 
         for (const field of fields) {
@@ -155,15 +178,15 @@ class ExternalMediaInliner {
                 const src = resourceModel.get(field);
 
                 if (src && src.startsWith(domain)) {
-                    const response = await this.#getRemoteMedia(src);
+                    const response = await this.getRemoteMedia(src);
 
                     let media;
                     if (response) {
-                        media = this.#extractFileDataFromResponse(src, response);
+                        media = await this.extractFileDataFromResponse(src, response);
                     }
 
                     if (media) {
-                        const filePath = await this.#storeMediaLocally(media);
+                        const filePath = await this.storeMediaLocally(media);
 
                         if (filePath) {
                             const inlinedSrc = `__GHOST_URL__${filePath}`;
@@ -186,12 +209,12 @@ class ExternalMediaInliner {
      * @param {string[]} fields - fields to inline
      * @param {string[]} domains - domains to inline media from
      */
-    async #inlineSimpleFields(resources, model, fields, domains) {
+    async inlineSimpleFields(resources, model, fields, domains) {
         logging.info(`Starting inlining external media for ${resources?.length} resources and with ${fields.join(', ')} fields`);
 
         for (const resource of resources) {
             try {
-                const updatedFields = await this.#inlineFields(resource, fields, domains);
+                const updatedFields = await this.inlineFields(resource, fields, domains);
 
                 if (Object.keys(updatedFields).length > 0) {
                     await model.edit(updatedFields, {
@@ -227,8 +250,8 @@ class ExternalMediaInliner {
 
         for (const post of posts) {
             try {
-                const inlinedMobiledoc = await this.#inlineMibiledoc(post.get('mobiledoc'), domains);
-                const updatedFields = await this.#inlineFields(post, postsInilingFields, domains);
+                const inlinedMobiledoc = await this.inlineMobiledoc(post.get('mobiledoc'), domains);
+                const updatedFields = await this.inlineFields(post, postsInilingFields, domains);
 
                 if (inlinedMobiledoc !== post.get('mobiledoc')) {
                     updatedFields.mobiledoc = inlinedMobiledoc;
@@ -258,7 +281,7 @@ class ExternalMediaInliner {
             'twitter_image'
         ];
 
-        await this.#inlineSimpleFields(postsMetas, this.#PostMetaModel, postsMetaInilingFields, domains);
+        await this.inlineSimpleFields(postsMetas, this.#PostMetaModel, postsMetaInilingFields, domains);
 
         const {data: tags} = await this.#TagModel.findPage({
             limit: 'all'
@@ -269,7 +292,7 @@ class ExternalMediaInliner {
             'twitter_image'
         ];
 
-        await this.#inlineSimpleFields(tags, this.#TagModel, tagInliningFields, domains);
+        await this.inlineSimpleFields(tags, this.#TagModel, tagInliningFields, domains);
 
         const {data: users} = await this.#UserModel.findPage({
             limit: 'all'
@@ -279,7 +302,7 @@ class ExternalMediaInliner {
             'cover_image'
         ];
 
-        await this.#inlineSimpleFields(users, this.#UserModel, userInliningFields, domains);
+        await this.inlineSimpleFields(users, this.#UserModel, userInliningFields, domains);
 
         logging.info('Finished inlining external media for posts, tags, and users');
     }
diff --git a/ghost/external-media-inliner/package.json b/ghost/external-media-inliner/package.json
index 547448f217..f59306e199 100644
--- a/ghost/external-media-inliner/package.json
+++ b/ghost/external-media-inliner/package.json
@@ -22,7 +22,7 @@
     "mocha": "10.2.0",
     "sinon": "15.2.0"
   },
-"dependencies": {
-    "mime-types": "2.1.35"
-}
+  "dependencies": {
+    "file-type": "16.5.4"
+  }
 }
diff --git a/ghost/external-media-inliner/test/ExternalMediaInliner.test.js b/ghost/external-media-inliner/test/ExternalMediaInliner.test.js
index 5bf3507f86..7a6ed9528a 100644
--- a/ghost/external-media-inliner/test/ExternalMediaInliner.test.js
+++ b/ghost/external-media-inliner/test/ExternalMediaInliner.test.js
@@ -1,4 +1,5 @@
 const assert = require('assert/strict');
+const fs = require('fs');
 const sinon = require('sinon');
 const nock = require('nock');
 const path = require('path');
@@ -7,6 +8,8 @@ const ExternalMediaInliner = require('../index');
 
 describe('ExternalMediaInliner', function () {
     let logging;
+    let ghostLogoPng;
+    let exeFile;
     let GIF1x1;
     let postModelStub;
     let postMetaModelStub;
@@ -15,6 +18,8 @@ describe('ExternalMediaInliner', function () {
 
     beforeEach(function () {
         // use a 1x1 gif in nock responses because it's really small and easy to work with
+        ghostLogoPng = fs.readFileSync(path.join(__dirname, 'fixtures', 'ghost-logo.png'));
+        exeFile = fs.readFileSync(path.join(__dirname, 'fixtures', 'fixture.exe'));
         GIF1x1 = Buffer.from('R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==', 'base64');
         logging = {
             info: sinon.stub(loggingLib, 'info'),
@@ -222,7 +227,7 @@ describe('ExternalMediaInliner', function () {
             const fileURL = 'https://img.stockfresh.com/files/f/inlined.exe';
             const requestMock = nock('https://img.stockfresh.com')
                 .get('/files/f/inlined.exe')
-                .reply(200, GIF1x1);
+                .reply(200, exeFile);
 
             const postModelInstanceStub = {
                 id: 'inlined-post-id',
@@ -526,4 +531,145 @@ describe('ExternalMediaInliner', function () {
             });
         });
     });
+
+    describe('Special URL & file type handling', function () {
+        it('Handles URLs with quotes', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/ghost-logo’s-cool.png';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get(encodeURI('/files/f/ghost-logo’s-cool.png'))
+                .reply(200, ghostLogoPng);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'ghost-logos-cool.png');
+            assert.equal(fileData.extension, '.png');
+        });
+
+        it('Handles URLs with spaces', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/ghost logo with spaces.png';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get(encodeURI('/files/f/ghost logo with spaces.png'))
+                .reply(200, ghostLogoPng);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'ghost-logo-with-spaces.png');
+            assert.equal(fileData.extension, '.png');
+        });
+
+        it('Handles URLs with no extension', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/ghost-logo';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get('/files/f/ghost-logo')
+                .reply(200, ghostLogoPng);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'ghost-logo.png');
+            assert.equal(fileData.extension, '.png');
+        });
+
+        it('Handles URLs with unicode characters', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/你好.png';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get(encodeURI('/files/f/你好.png'))
+                .reply(200, ghostLogoPng);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'ni-hao.png');
+            assert.equal(fileData.extension, '.png');
+        });
+
+        it('Handles URLs with no scheme', async function () {
+            const imageURL = '//img.stockfresh.com/files/f/ghost-logo.png';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get('/files/f/ghost-logo.png')
+                .reply(200, ghostLogoPng);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'ghost-logo.png');
+            assert.equal(fileData.extension, '.png');
+        });
+
+        it('Handles URLs with query params', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/ghost-logo.png?version=1&size=large';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get('/files/f/ghost-logo.png?version=1&size=large')
+                .reply(200, ghostLogoPng);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'ghost-logo-version-1-size-large.png');
+            assert.equal(fileData.extension, '.png');
+        });
+
+        it('Handles URLs with duplicated characters', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/ghost---logo.png';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get('/files/f/ghost---logo.png')
+                .reply(200, ghostLogoPng);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'ghost---logo.png');
+            assert.equal(fileData.extension, '.png');
+        });
+
+        it('Handles falling back to `content-type` for type', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/photo.gif?v=1&s=2';
+            const requestMock = nock('https://img.stockfresh.com')
+                .defaultReplyHeaders({
+                    'content-type': 'image/gif'
+                })
+                .get('/files/f/photo.gif?v=1&s=2')
+                .reply(200);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'photo-v-1-s-2.gif');
+            assert.equal(fileData.extension, '.gif');
+        });
+
+        it('Handles falling back to file path for type', async function () {
+            const imageURL = 'https://img.stockfresh.com/files/f/photo.gif?v=1&s=2';
+            const requestMock = nock('https://img.stockfresh.com')
+                .get('/files/f/photo.gif?v=1&s=2')
+                .reply(200);
+
+            const inliner = new ExternalMediaInliner({});
+            const response = await inliner.getRemoteMedia(imageURL);
+            const fileData = await inliner.extractFileDataFromResponse(imageURL, response);
+
+            assert.ok(requestMock.isDone());
+            assert.equal(fileData.filename, 'photo-v-1-s-2.gif');
+            assert.equal(fileData.extension, '.gif');
+        });
+    });
 });
+
diff --git a/ghost/external-media-inliner/test/fixtures/fixture.exe b/ghost/external-media-inliner/test/fixtures/fixture.exe
new file mode 100644
index 0000000000..9b0c9e0594
Binary files /dev/null and b/ghost/external-media-inliner/test/fixtures/fixture.exe differ
diff --git a/ghost/external-media-inliner/test/fixtures/ghost-logo.png b/ghost/external-media-inliner/test/fixtures/ghost-logo.png
new file mode 100644
index 0000000000..8ade814dc5
Binary files /dev/null and b/ghost/external-media-inliner/test/fixtures/ghost-logo.png differ
diff --git a/yarn.lock b/yarn.lock
index f68206d6ea..f31dfdbf5a 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -7499,6 +7499,11 @@
     "@tiptap/extension-bubble-menu" "^2.1.12"
     "@tiptap/extension-floating-menu" "^2.1.12"
 
+"@tokenizer/token@^0.3.0":
+  version "0.3.0"
+  resolved "https://registry.yarnpkg.com/@tokenizer/token/-/token-0.3.0.tgz#fe98a93fe789247e998c75e74e9c7c63217aa276"
+  integrity sha512-OvjF+z51L3ov0OyAU0duzsYuvO01PH7x4t6DJx+guahgTnBHkhJdG7soQeTSFLWN3efnHyibZ4Z8l2EuWwJN3A==
+
 "@tootallnate/once@1":
   version "1.1.2"
   resolved "https://registry.yarnpkg.com/@tootallnate/once/-/once-1.1.2.tgz#ccb91445360179a04e7fe6aff78c00ffc1eeaf82"
@@ -17704,6 +17709,15 @@ file-system-cache@2.3.0, file-system-cache@^2.0.0:
     fs-extra "11.1.1"
     ramda "0.29.0"
 
+file-type@16:
+  version "16.5.4"
+  resolved "https://registry.yarnpkg.com/file-type/-/file-type-16.5.4.tgz#474fb4f704bee427681f98dd390058a172a6c2fd"
+  integrity sha512-/yFHK0aGjFEgDJjEKP0pWCplsPFPhwyfwevf/pVxiN0tmE4L9LmwWxWukdJSHdoCli4VgQLehjJtwQBnqmsKcw==
+  dependencies:
+    readable-web-to-node-stream "^3.0.0"
+    strtok3 "^6.2.4"
+    token-types "^4.1.1"
+
 file-uri-to-path@1.0.0:
   version "1.0.0"
   resolved "https://registry.yarnpkg.com/file-uri-to-path/-/file-uri-to-path-1.0.0.tgz#553a7b8446ff6f684359c445f1e37a05dacc33dd"
@@ -23101,7 +23115,7 @@ mime-types@2.1.13:
   dependencies:
     mime-db "~1.25.0"
 
-mime-types@2.1.35, mime-types@^2.1.12, mime-types@^2.1.18, mime-types@^2.1.25, mime-types@^2.1.26, mime-types@^2.1.27, mime-types@~2.1.19, mime-types@~2.1.24, mime-types@~2.1.34:
+mime-types@^2.1.12, mime-types@^2.1.18, mime-types@^2.1.25, mime-types@^2.1.26, mime-types@^2.1.27, mime-types@~2.1.19, mime-types@~2.1.24, mime-types@~2.1.34:
   version "2.1.35"
   resolved "https://registry.yarnpkg.com/mime-types/-/mime-types-2.1.35.tgz#381a871b62a734450660ae3deee44813f70d959a"
   integrity sha512-ZDY+bPm5zTTF+YpCrAU9nK0UgICYPT0QtT1NZWFv4s++TNkcgVaT0g6+4R2uI4MjQjzysHB1zxuWL50hzaeXiw==
@@ -25085,6 +25099,11 @@ pbkdf2@^3.0.3:
     safe-buffer "^5.0.1"
     sha.js "^2.4.8"
 
+peek-readable@^4.1.0:
+  version "4.1.0"
+  resolved "https://registry.yarnpkg.com/peek-readable/-/peek-readable-4.1.0.tgz#4ece1111bf5c2ad8867c314c81356847e8a62e72"
+  integrity sha512-ZI3LnwUv5nOGbQzD9c2iDG6toheuXSZP5esSHBjopsXH4dg19soufvpUGA3uohi5anFtGb2lhAVdHzH6R/Evvg==
+
 peek-stream@^1.1.0:
   version "1.1.3"
   resolved "https://registry.yarnpkg.com/peek-stream/-/peek-stream-1.1.3.tgz#3b35d84b7ccbbd262fff31dc10da56856ead6d67"
@@ -27123,6 +27142,13 @@ readable-stream@~1.0.2, readable-stream@~1.0.26, readable-stream@~1.0.26-4:
     isarray "0.0.1"
     string_decoder "~0.10.x"
 
+readable-web-to-node-stream@^3.0.0:
+  version "3.0.2"
+  resolved "https://registry.yarnpkg.com/readable-web-to-node-stream/-/readable-web-to-node-stream-3.0.2.tgz#5d52bb5df7b54861fd48d015e93a2cb87b3ee0bb"
+  integrity sha512-ePeK6cc1EcKLEhJFt/AebMCLL+GgSKhuygrZ/GLaKZYEecIgIECf4UaUuaByiGtzckwR4ain9VzUh95T1exYGw==
+  dependencies:
+    readable-stream "^3.6.0"
+
 readdir-glob@^1.0.0:
   version "1.1.2"
   resolved "https://registry.yarnpkg.com/readdir-glob/-/readdir-glob-1.1.2.tgz#b185789b8e6a43491635b6953295c5c5e3fd224c"
@@ -29319,6 +29345,14 @@ strong-log-transformer@^2.1.0:
     minimist "^1.2.0"
     through "^2.3.4"
 
+strtok3@^6.2.4:
+  version "6.3.0"
+  resolved "https://registry.yarnpkg.com/strtok3/-/strtok3-6.3.0.tgz#358b80ffe6d5d5620e19a073aa78ce947a90f9a0"
+  integrity sha512-fZtbhtvI9I48xDSywd/somNqgUHl2L2cstmXCCif0itOf96jeW18MBSyrLuNicYQVkvpOxkZtkzujiTJ9LW5Jw==
+  dependencies:
+    "@tokenizer/token" "^0.3.0"
+    peek-readable "^4.1.0"
+
 style-loader@^2.0.0:
   version "2.0.0"
   resolved "https://registry.yarnpkg.com/style-loader/-/style-loader-2.0.0.tgz#9669602fd4690740eaaec137799a03addbbc393c"
@@ -30126,6 +30160,14 @@ toidentifier@1.0.1:
   resolved "https://registry.yarnpkg.com/toidentifier/-/toidentifier-1.0.1.tgz#3be34321a88a820ed1bd80dfaa33e479fbb8dd35"
   integrity sha512-o5sSPKEkg/DIQNmH43V0/uerLrpzVedkUh8tGNvaeXpfpuwjKenlSox/2O/BTlZUtEe+JG7s5YhEz608PlAHRA==
 
+token-types@^4.1.1:
+  version "4.2.1"
+  resolved "https://registry.yarnpkg.com/token-types/-/token-types-4.2.1.tgz#0f897f03665846982806e138977dbe72d44df753"
+  integrity sha512-6udB24Q737UD/SDsKAHI9FCRP7Bqc9D/MQUV02ORQg5iskjtLJlZJNdN4kKtcdtwCeWIwIHDGaUsTsCCAa8sFQ==
+  dependencies:
+    "@tokenizer/token" "^0.3.0"
+    ieee754 "^1.2.1"
+
 toml@3.0.0:
   version "3.0.0"
   resolved "https://registry.yarnpkg.com/toml/-/toml-3.0.0.tgz#342160f1af1904ec9d204d03a5d61222d762c5ee"