diff --git a/pyproject.toml b/pyproject.toml
index 193c0cc3..b3529aa9 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -40,6 +40,7 @@ dependencies = [
     "dateparser >= 1.1.1",
     "defusedxml == 0.7.1",
     "fastapi == 0.77.1",
+    "python-multipart >= 0.0.5",
     "jinja2 == 3.1.2",
     "openai >= 0.27.0, < 1.0.0",
     "tiktoken >= 0.3.2",
diff --git a/src/interface/desktop/main.js b/src/interface/desktop/main.js
index 4f8891cf..9b2ee49c 100644
--- a/src/interface/desktop/main.js
+++ b/src/interface/desktop/main.js
@@ -8,7 +8,6 @@ const {dialog} = require('electron');
 
 const cron = require('cron').CronJob;
 const axios = require('axios');
-const { Readable } = require('stream');
 
 const KHOJ_URL = 'http://127.0.0.1:42110'
 
@@ -65,7 +64,7 @@ const schema = {
 
 var state = {}
 
-const store = new Store({schema});
+const store = new Store({ schema });
 
 console.log(store);
 
@@ -86,37 +85,48 @@ function handleSetTitle (event, title) {
     });
 }
 
+function filenameToMimeType (filename) {
+    const extension = filename.split('.').pop();
+    switch (extension) {
+        case 'pdf':
+            return 'application/pdf';
+        case 'png':
+            return 'image/png';
+        case 'jpg':
+        case 'jpeg':
+            return 'image/jpeg';
+        case 'md':
+        case 'markdown':
+            return 'text/markdown';
+        case 'org':
+            return 'text/org';
+        default:
+            return 'text/plain';
+    }
+}
+
 function pushDataToKhoj (regenerate = false) {
     let filesToPush = [];
-    const files = store.get('files');
-    const folders = store.get('folders');
-    state = {
-        completed: true
+    const files = store.get('files') || [];
+    const folders = store.get('folders') || [];
+    state = { completed: true }
+
+    for (const file of files) {
+        filesToPush.push(file.path);
     }
 
-    if (files) {
-        for (file of files) {
-            filesToPush.push(file.path);
-        }
-    }
-    if (folders) {
-        for (folder of folders) {
-            const files = fs.readdirSync(folder.path, { withFileTypes: true });
-            for (file of files) {
-                if (file.isFile() && validFileTypes.includes(file.name.split('.').pop())) {
-                    filesToPush.push(path.join(folder.path, file.name));
-                }
+    for (const folder of folders) {
+        const files = fs.readdirSync(folder.path, { withFileTypes: true });
+        for (const file of files) {
+            if (file.isFile() && validFileTypes.includes(file.name.split('.').pop())) {
+                filesToPush.push(path.join(folder.path, file.name));
             }
         }
     }
 
-    let data = {
-        files: []
-    }
-
     const lastSync = store.get('lastSync') || [];
-
-    for (file of filesToPush) {
+    const formData = new FormData();
+    for (const file of filesToPush) {
         const stats = fs.statSync(file);
         if (!regenerate) {
             if (stats.mtime.toISOString() < lastSync.find((syncedFile) => syncedFile.path === file)?.datetime) {
@@ -125,18 +135,10 @@ function pushDataToKhoj (regenerate = false) {
         }
 
         try {
-            let rawData;
-            // If the file is a PDF or IMG file, read it as a binary file
-            if (binaryFileTypes.includes(file.split('.').pop())) {
-                rawData = fs.readFileSync(file).toString('base64');
-            } else {
-                rawData = fs.readFileSync(file, 'utf8');
-            }
-
-            data.files.push({
-                path: file,
-                content: rawData
-            });
+            encoding = binaryFileTypes.includes(file.split('.').pop()) ? "binary" : "utf8";
+            mimeType = filenameToMimeType(file) + (encoding === "utf8" ? "; charset=UTF-8" : "");
+            fileObj = new Blob([fs.createReadStream(file, encoding)], { type: mimeType });
+            formData.append('files', fileObj, file);
             state[file] = {
                 success: true,
             }
@@ -151,44 +153,37 @@ function pushDataToKhoj (regenerate = false) {
 
     for (const syncedFile of lastSync) {
         if (!filesToPush.includes(syncedFile.path)) {
-            data.files.push({
-                path: syncedFile.path,
-                content: ""
-            });
+            fileObj = new Blob([""], { type: filenameToMimeType(syncedFile.path) });
+            formData.append('files', fileObj, syncedFile.path);
         }
     }
 
-    const headers = { 'x-api-key': 'secret', 'Content-Type': 'application/json' };
-
-    const stream = new Readable({
-        read() {
-            this.push(JSON.stringify(data));
-            this.push(null);
-        }
-    });
-
-    const hostURL = store.get('hostURL') || KHOJ_URL;
-
-    axios.post(`${hostURL}/v1/indexer/batch?regenerate=${regenerate}`, stream, { headers })
-        .then(response => {
-            console.log(response.data);
-            const win = BrowserWindow.getAllWindows()[0];
-            win.webContents.send('update-state', state);
-            let lastSync = [];
-            for (const file of filesToPush) {
-                lastSync.push({
-                    path: file,
-                    datetime: new Date().toISOString()
-                });
-            }
-            store.set('lastSync', lastSync);
-        })
-        .catch(error => {
-            console.error(error);
-            state['completed'] = false
-            const win = BrowserWindow.getAllWindows()[0];
-            win.webContents.send('update-state', state);
-        });
+    if (!!formData?.entries()?.next().value) {
+        const hostURL = store.get('hostURL') || KHOJ_URL;
+        const headers = {
+            'x-api-key': 'secret'
+        };
+        axios.post(`${hostURL}/api/v1/index/update?force=${regenerate}&client=desktop`, formData, { headers })
+            .then(response => {
+                console.log(response.data);
+                const win = BrowserWindow.getAllWindows()[0];
+                win.webContents.send('update-state', state);
+                let lastSync = [];
+                for (const file of filesToPush) {
+                    lastSync.push({
+                        path: file,
+                        datetime: new Date().toISOString()
+                    });
+                }
+                store.set('lastSync', lastSync);
+            })
+            .catch(error => {
+                console.error(error);
+                state['completed'] = false
+                const win = BrowserWindow.getAllWindows()[0];
+                win.webContents.send('update-state', state);
+            });
+    }
 }
 
 pushDataToKhoj();
diff --git a/src/interface/emacs/khoj.el b/src/interface/emacs/khoj.el
index 09de2f93..70980241 100644
--- a/src/interface/emacs/khoj.el
+++ b/src/interface/emacs/khoj.el
@@ -93,6 +93,15 @@
   :group 'khoj
   :type 'number)
 
+(defcustom khoj-server-api-key "secret"
+  "API Key to Khoj server."
+  :group 'khoj
+  :type 'string)
+
+(defcustom khoj-index-interval 3600
+  "Interval (in seconds) to wait before updating content index."
+  :group 'khoj
+  :type 'number)
 
 (defcustom khoj-default-content-type "org"
   "The default content type to perform search on."
@@ -125,6 +134,12 @@
 (defvar khoj--search-on-idle-timer nil
   "Idle timer to trigger incremental search.")
 
+(defvar khoj--index-timer nil
+  "Timer to trigger content indexing.")
+
+(defvar khoj--indexed-files '()
+  "Files that were indexed in previous content indexing run.")
+
 (declare-function org-element-property "org-mode" (PROPERTY ELEMENT))
 (declare-function org-element-type "org-mode" (ELEMENT))
 (declare-function markdown-mode "markdown-mode" ())
@@ -375,9 +390,10 @@ CONFIG is json obtained from Khoj config API."
           (string-join "/"))))
 
 (defun khoj--server-configure ()
-  "Configure the the Khoj server for search and chat."
+  "Configure the Khoj server for search and chat."
   (interactive)
   (let* ((org-directory-regexes (or (mapcar (lambda (dir) (format "%s/**/*.org" dir)) khoj-org-directories) json-null))
+         (url-request-method "GET")
          (current-config
           (with-temp-buffer
             (url-insert-file-contents (format "%s/api/config/data" khoj-server-url))
@@ -389,7 +405,6 @@ CONFIG is json obtained from Khoj config API."
          (default-index-dir (khoj--get-directory-from-config default-config '(content-type org embeddings-file)))
          (default-chat-dir (khoj--get-directory-from-config default-config '(processor conversation conversation-logfile)))
          (chat-model (or khoj-chat-model (alist-get 'chat-model (alist-get 'openai (alist-get 'conversation (alist-get 'processor default-config))))))
-         (default-model (alist-get 'model (alist-get 'conversation (alist-get 'processor default-config))))
          (enable-offline-chat (or khoj-chat-offline (alist-get 'enable-offline-chat (alist-get 'conversation (alist-get 'processor default-config)))))
          (config (or current-config default-config)))
 
@@ -519,9 +534,75 @@ CONFIG is json obtained from Khoj config API."
       (khoj--server-configure))))
 
 
-;; -----------------------------------------------
-;; Extract and Render Entries of each Content Type
-;; -----------------------------------------------
+;; -------------------
+;; Khoj Index Content
+;; -------------------
+
+(defun khoj--server-index-files (&optional force content-type file-paths)
+  "Send files at `FILE-PATHS' to the Khoj server to index for search and chat.
+`FORCE' re-indexes all files of `CONTENT-TYPE' even if they are already indexed."
+  (interactive)
+  (let ((boundary (format "-------------------------%d" (random (expt 10 10))))
+        (files-to-index (or file-paths
+                            (append (mapcan (lambda (dir) (directory-files-recursively dir "\\.org$")) khoj-org-directories) khoj-org-files)))
+        (type-query (if (or (equal content-type "all") (not content-type)) "" (format "t=%s" content-type)))
+        (inhibit-message t)
+        (message-log-max nil))
+    (let ((url-request-method "POST")
+          (url-request-data (khoj--render-files-as-request-body files-to-index khoj--indexed-files boundary))
+          (url-request-extra-headers `(("content-type" . ,(format "multipart/form-data; boundary=%s" boundary))
+                                       ("x-api-key" . ,khoj-server-api-key))))
+      (with-current-buffer
+          (url-retrieve (format "%s/api/v1/index/update?%s&force=%s&client=emacs" khoj-server-url type-query (or force "false"))
+                        ;; render response from indexing API endpoint on server
+                        (lambda (status)
+                          (if (not status)
+                              (message "khoj.el: %scontent index %supdated" (if content-type (format "%s " content-type) "") (if force "force " ""))
+                            (with-current-buffer (current-buffer)
+                              (goto-char "\n\n")
+                              (message "khoj.el: Failed to %supdate %s content index. Status: %s. Response: %s"
+                                       (if force "force " "")
+                                       content-type
+                                       status
+                                       (string-trim (buffer-substring-no-properties (point) (point-max)))))))
+                        nil t t)))
+    (setq khoj--indexed-files files-to-index)))
+
+(defun khoj--render-files-as-request-body (files-to-index previously-indexed-files boundary)
+  "Render `FILES-TO-INDEX', `PREVIOUSLY-INDEXED-FILES' as multi-part form body.
+Use `BOUNDARY' to separate files. This is sent to Khoj server as a POST request."
+  (with-temp-buffer
+    (set-buffer-multibyte nil)
+    (insert "\n")
+    (dolist (file-to-index files-to-index)
+      (insert (format "--%s\r\n" boundary))
+      (insert (format "Content-Disposition: form-data; name=\"files\"; filename=\"%s\"\r\n" file-to-index))
+      (insert "Content-Type: text/org\r\n\r\n")
+      (insert (with-temp-buffer
+                (insert-file-contents-literally file-to-index)
+                (buffer-string)))
+      (insert "\r\n"))
+    (dolist (file-to-index previously-indexed-files)
+      (when (not (member file-to-index files-to-index))
+        (insert (format "--%s\r\n" boundary))
+        (insert (format "Content-Disposition: form-data; name=\"files\"; filename=\"%s\"\r\n" file-to-index))
+        (insert "Content-Type: text/org\r\n\r\n")
+        (insert "")
+        (insert "\r\n")))
+    (insert (format "--%s--\r\n" boundary))
+    (buffer-string)))
+
+;; Cancel any running indexing timer, first
+(when khoj--index-timer
+    (cancel-timer khoj--index-timer))
+;; Send files to index on server every `khoj-index-interval' seconds
+(setq khoj--index-timer
+      (run-with-timer 60 khoj-index-interval 'khoj--server-index-files))
+
+
+;; -------------------------------------------
+;; Render Response from Khoj server for Emacs
+;; -------------------------------------------
 
 (defun khoj--extract-entries-as-markdown (json-response query)
   "Convert JSON-RESPONSE, QUERY from API to markdown entries."
@@ -1029,17 +1110,20 @@ Paragraph only starts at first text after blank line."
 ;; Khoj Menu
 ;; ---------
 
-(transient-define-argument khoj--content-type-switch ()
-  :class 'transient-switches
-  :argument-format "--content-type=%s"
-  :argument-regexp ".+"
-  ;; set content type to: last used > based on current buffer > default type
-  :init-value (lambda (obj) (oset obj value (format "--content-type=%s" (or khoj--content-type (khoj--buffer-name-to-content-type (buffer-name))))))
-  ;; dynamically set choices to content types enabled on khoj backend
-  :choices (or (ignore-errors (mapcar #'symbol-name (khoj--get-enabled-content-types))) '("all" "org" "markdown" "pdf" "image")))
+(defun khoj--setup-and-show-menu ()
+  "Create Transient menu for khoj and show it."
+  ;; Create the Khoj Transient menu
+  (transient-define-argument khoj--content-type-switch ()
+    :class 'transient-switches
+    :argument-format "--content-type=%s"
+    :argument-regexp ".+"
+    ;; set content type to: last used > based on current buffer > default type
+    :init-value (lambda (obj) (oset obj value (format "--content-type=%s" (or khoj--content-type (khoj--buffer-name-to-content-type (buffer-name))))))
+    ;; dynamically set choices to content types enabled on khoj backend
+    :choices (or (ignore-errors (mapcar #'symbol-name (khoj--get-enabled-content-types))) '("all" "org" "markdown" "pdf" "image")))
 
-(transient-define-suffix khoj--search-command (&optional args)
-  (interactive (list (transient-args transient-current-command)))
+  (transient-define-suffix khoj--search-command (&optional args)
+    (interactive (list (transient-args transient-current-command)))
     (progn
       ;; set content type to: specified > last used > based on current buffer > default type
       (setq khoj--content-type (or (transient-arg-value "--content-type=" args) (khoj--buffer-name-to-content-type (buffer-name))))
@@ -1048,9 +1132,9 @@ Paragraph only starts at first text after blank line."
       ;; trigger incremental search
       (call-interactively #'khoj-incremental)))
 
-(transient-define-suffix khoj--find-similar-command (&optional args)
-  "Find items similar to current item at point."
-  (interactive (list (transient-args transient-current-command)))
+  (transient-define-suffix khoj--find-similar-command (&optional args)
+    "Find items similar to current item at point."
+    (interactive (list (transient-args transient-current-command)))
     (progn
       ;; set content type to: specified > last used > based on current buffer > default type
       (setq khoj--content-type (or (transient-arg-value "--content-type=" args) (khoj--buffer-name-to-content-type (buffer-name))))
@@ -1058,37 +1142,38 @@ Paragraph only starts at first text after blank line."
       (setq khoj-results-count (or (transient-arg-value "--results-count=" args) khoj-results-count))
       (khoj--find-similar khoj--content-type)))
 
-(transient-define-suffix khoj--update-command (&optional args)
-  "Call khoj API to update index of specified content type."
-  (interactive (list (transient-args transient-current-command)))
-  (let* ((force-update (if (member "--force-update" args) "true" "false"))
-         ;; set content type to: specified > last used > based on current buffer > default type
-         (content-type (or (transient-arg-value "--content-type=" args) (khoj--buffer-name-to-content-type (buffer-name))))
-         (type-query (if (equal content-type "all") "" (format "t=%s" content-type)))
-         (update-url (format "%s/api/update?%s&force=%s&client=emacs" khoj-server-url type-query force-update))
-         (url-request-method "GET"))
-    (progn
-      (setq khoj--content-type content-type)
-      (url-retrieve update-url (lambda (_) (message "khoj.el: %s index %supdated!" content-type (if (member "--force-update" args) "force " "")))))))
+  (transient-define-suffix khoj--update-command (&optional args)
+    "Call khoj API to update index of specified content type."
+    (interactive (list (transient-args transient-current-command)))
+    (let* ((force-update (if (member "--force-update" args) "true" "false"))
+           ;; set content type to: specified > last used > based on current buffer > default type
+           (content-type (or (transient-arg-value "--content-type=" args) (khoj--buffer-name-to-content-type (buffer-name))))
+           (url-request-method "GET"))
+      (progn
+        (setq khoj--content-type content-type)
+        (khoj--server-index-files force-update content-type))))
 
-(transient-define-suffix khoj--chat-command (&optional _)
-  "Command to Chat with Khoj."
-  (interactive (list (transient-args transient-current-command)))
-  (khoj--chat))
+  (transient-define-suffix khoj--chat-command (&optional _)
+    "Command to Chat with Khoj."
+    (interactive (list (transient-args transient-current-command)))
+    (khoj--chat))
 
-(transient-define-prefix khoj--menu ()
-  "Create Khoj Menu to Configure and Execute Commands."
-  [["Configure Search"
-    ("n" "Results Count" "--results-count=" :init-value (lambda (obj) (oset obj value (format "%s" khoj-results-count))))
-    ("t" "Content Type" khoj--content-type-switch)]
-   ["Configure Update"
-    ("-f" "Force Update" "--force-update")]]
-  [["Act"
-    ("c" "Chat" khoj--chat-command)
-    ("s" "Search" khoj--search-command)
-    ("f" "Find Similar" khoj--find-similar-command)
-    ("u" "Update" khoj--update-command)
-    ("q" "Quit" transient-quit-one)]])
+  (transient-define-prefix khoj--menu ()
+    "Create Khoj Menu to Configure and Execute Commands."
+    [["Configure Search"
+      ("n" "Results Count" "--results-count=" :init-value (lambda (obj) (oset obj value (format "%s" khoj-results-count))))
+      ("t" "Content Type" khoj--content-type-switch)]
+     ["Configure Update"
+      ("-f" "Force Update" "--force-update")]]
+    [["Act"
+      ("c" "Chat" khoj--chat-command)
+      ("s" "Search" khoj--search-command)
+      ("f" "Find Similar" khoj--find-similar-command)
+      ("u" "Update" khoj--update-command)
+      ("q" "Quit" transient-quit-one)]])
+
+  ;; Show the Khoj Transient menu
+  (khoj--menu))
 
 
 ;; ----------
@@ -1101,7 +1186,7 @@ Paragraph only starts at first text after blank line."
   (interactive)
   (when khoj-auto-setup
     (khoj-setup t))
-  (khoj--menu))
+  (khoj--setup-and-show-menu))
 
 (provide 'khoj)
 
diff --git a/src/interface/emacs/tests/khoj-tests.el b/src/interface/emacs/tests/khoj-tests.el
index 8242d30b..c0d9f4a6 100644
--- a/src/interface/emacs/tests/khoj-tests.el
+++ b/src/interface/emacs/tests/khoj-tests.el
@@ -206,6 +206,64 @@ Rule everything\n")
       "Rule everything"))
     ))
 
+
+;; -------------------------------------
+;; Test Helpers to Index Content
+;; -------------------------------------
+
+(ert-deftest khoj-tests--render-files-to-add-request-body ()
+  "Test files are formatted into a multi-part http request body"
+  (let ((upgrade-file (make-temp-file "upgrade" nil ".org" "# Become God\n## Upgrade\n\nPenance to Immortality\n\n"))
+        (act-file (make-temp-file "act" nil ".org" "## Act\n\nRule everything\n\n")))
+    (unwind-protect
+        (progn
+          (should
+           (equal
+            (khoj--render-files-as-request-body (list upgrade-file act-file) '() "khoj")
+            (format
+            "\n--khoj\r\n\
+Content-Disposition: form-data; name=\"files\"; filename=\"%s\"\r\n\
+Content-Type: text/org\r\n\r\n\
+# Become God\n\
+## Upgrade\n\n\
+Penance to Immortality\n\n\r
+--khoj\r\n\
+Content-Disposition: form-data; name=\"files\"; filename=\"%s\"\r\n\
+Content-Type: text/org\r\n\r\n\
+## Act\n\n\
+Rule everything\n\n\r\n\
+--khoj--\r\n" upgrade-file act-file))))
+      (delete-file upgrade-file)
+      (delete-file act-file))))
+
+(ert-deftest khoj-tests--render-files-to-add-delete-in-request-body ()
+  "Test files are formatted into a multi-part http request body"
+  (let ((upgrade-file (make-temp-file "upgrade" nil ".org" "# Become God\n## Upgrade\n\nPenance to Immortality\n\n"))
+        (act-file (make-temp-file "act" nil ".org" "## Act\n\nRule everything\n\n")))
+    (unwind-protect
+        (progn
+          (should
+           (equal
+            (khoj--render-files-as-request-body (list upgrade-file act-file) (list upgrade-file act-file "/tmp/deleted-file.org") "khoj")
+            (format
+            "\n--khoj\r\n\
+Content-Disposition: form-data; name=\"files\"; filename=\"%s\"\r\n\
+Content-Type: text/org\r\n\r\n\
+# Become God\n\
+## Upgrade\n\n\
+Penance to Immortality\n\n\r
+--khoj\r\n\
+Content-Disposition: form-data; name=\"files\"; filename=\"%s\"\r\n\
+Content-Type: text/org\r\n\r\n\
+## Act\n\n\
+Rule everything\n\n\r
+--khoj\r\n\
+Content-Disposition: form-data; name=\"files\"; filename=\"%s\"\r\n\
+Content-Type: text/org\r\n\r\n\
+\r
+--khoj--\r\n" upgrade-file act-file "/tmp/deleted-file.org"))))
+      (delete-file upgrade-file)
+      (delete-file act-file))))
 
 (provide 'khoj-tests)
 
diff --git a/src/interface/obsidian/src/main.ts b/src/interface/obsidian/src/main.ts
index 935945dd..1fbed55f 100644
--- a/src/interface/obsidian/src/main.ts
+++ b/src/interface/obsidian/src/main.ts
@@ -1,12 +1,13 @@
-import { Notice, Plugin } from 'obsidian';
+import { Notice, Plugin, TFile } from 'obsidian';
 import { KhojSetting, KhojSettingTab, DEFAULT_SETTINGS } from 'src/settings'
 import { KhojSearchModal } from 'src/search_modal'
 import { KhojChatModal } from 'src/chat_modal'
-import { configureKhojBackend } from './utils';
+import { configureKhojBackend, updateContentIndex } from './utils';
 
 
 export default class Khoj extends Plugin {
     settings: KhojSetting;
+    indexingTimer: NodeJS.Timeout;
 
     async onload() {
         await this.loadSettings();
@@ -54,6 +55,15 @@ export default class Khoj extends Plugin {
 
         // Add a settings tab so the user can configure khoj
         this.addSettingTab(new KhojSettingTab(this.app, this));
+
+        // Add scheduled job to update index every 60 minutes
+        this.indexingTimer = setInterval(async () => {
+            if (this.settings.autoConfigure) {
+                this.settings.lastSyncedFiles = await updateContentIndex(
+                    this.app.vault, this.settings, this.settings.lastSyncedFiles
+                );
+            }
+        }, 60 * 60 * 1000);
     }
 
     async loadSettings() {
@@ -72,4 +82,12 @@ export default class Khoj extends Plugin {
         }
         this.saveData(this.settings);
     }
+
+    async onunload() {
+        // Remove scheduled job to update index at regular cadence
+        if (this.indexingTimer)
+            clearInterval(this.indexingTimer);
+
+        this.unload();
+    }
 }
diff --git a/src/interface/obsidian/src/settings.ts b/src/interface/obsidian/src/settings.ts
index c013f10c..9b672659 100644
--- a/src/interface/obsidian/src/settings.ts
+++ b/src/interface/obsidian/src/settings.ts
@@ -1,5 +1,6 @@
-import { App, Notice, PluginSettingTab, request, Setting } from 'obsidian';
+import { App, Notice, PluginSettingTab, request, Setting, TFile } from 'obsidian';
 import Khoj from 'src/main';
+import { updateContentIndex } from './utils';
 
 export interface KhojSetting {
     enableOfflineChat: boolean;
@@ -8,6 +9,7 @@ export interface KhojSetting {
     khojUrl: string;
     connectedToBackend: boolean;
     autoConfigure: boolean;
+    lastSyncedFiles: TFile[];
 }
 
 export const DEFAULT_SETTINGS: KhojSetting = {
@@ -17,6 +19,7 @@ export const DEFAULT_SETTINGS: KhojSetting = {
     connectedToBackend: false,
     autoConfigure: true,
     openaiApiKey: '',
+    lastSyncedFiles: []
 }
 
 export class KhojSettingTab extends PluginSettingTab {
@@ -118,8 +121,9 @@ export class KhojSettingTab extends PluginSettingTab {
                     }, 300);
                     this.plugin.registerInterval(progress_indicator);
 
-                    await request(`${this.plugin.settings.khojUrl}/api/update?t=markdown&force=true&client=obsidian`);
-                    await request(`${this.plugin.settings.khojUrl}/api/update?t=pdf&force=true&client=obsidian`);
+                    this.plugin.settings.lastSyncedFiles = await updateContentIndex(
+                        this.app.vault, this.plugin.settings, this.plugin.settings.lastSyncedFiles, true
+                    );
                     new Notice('✅ Updated Khoj index.');
 
                     // Reset button once index is updated
diff --git a/src/interface/obsidian/src/utils.ts b/src/interface/obsidian/src/utils.ts
index 920da583..7e32eccd 100644
--- a/src/interface/obsidian/src/utils.ts
+++ b/src/interface/obsidian/src/utils.ts
@@ -1,4 +1,4 @@
-import { FileSystemAdapter, Notice, RequestUrlParam, request, Vault, Modal } from 'obsidian';
+import { FileSystemAdapter, Notice, RequestUrlParam, request, Vault, Modal, TFile } from 'obsidian';
 import { KhojSetting } from 'src/settings'
 
 export function getVaultAbsolutePath(vault: Vault): string {
@@ -22,10 +22,70 @@ interface ProcessorData {
     };
 }
 
+function fileExtensionToMimeType (extension: string): string {
+    switch (extension) {
+        case 'pdf':
+            return 'application/pdf';
+        case 'png':
+            return 'image/png';
+        case 'jpg':
+        case 'jpeg':
+            return 'image/jpeg';
+        case 'md':
+        case 'markdown':
+            return 'text/markdown';
+        case 'org':
+            return 'text/org';
+        default:
+            return 'text/plain';
+    }
+}
+
+export async function updateContentIndex(vault: Vault, setting: KhojSetting, lastSyncedFiles: TFile[], regenerate: boolean = false): Promise<TFile[]> {
+    // Get all markdown, pdf files in the vault
+    console.log(`Khoj: Updating Khoj content index...`)
+    const files = vault.getFiles().filter(file => file.extension === 'md' || file.extension === 'pdf');
+    const binaryFileTypes = ['pdf', 'png', 'jpg', 'jpeg']
+    let countOfFilesToIndex = 0;
+    let countOfFilesToDelete = 0;
+
+    // Add all files to index as multipart form data
+    const formData = new FormData();
+    for (const file of files) {
+        countOfFilesToIndex++;
+        const encoding = binaryFileTypes.includes(file.extension) ? "binary" : "utf8";
+        const mimeType = fileExtensionToMimeType(file.extension) + (encoding === "utf8" ? "; charset=UTF-8" : "");
+        const fileContent = await vault.read(file);
+        formData.append('files', new Blob([fileContent], { type: mimeType }), file.path);
+    }
+
+    // Add any previously synced files to be deleted to multipart form data
+    for (const lastSyncedFile of lastSyncedFiles) {
+        if (!files.includes(lastSyncedFile)) {
+            countOfFilesToDelete++;
+            formData.append('files', new Blob([]), lastSyncedFile.path);
+        }
+    }
+
+    // Call Khoj backend to update index with all markdown, pdf files
+    const response = await fetch(`${setting.khojUrl}/api/v1/index/update?force=${regenerate}&client=obsidian`, {
+        method: 'POST',
+        headers: {
+            'x-api-key': 'secret',
+        },
+        body: formData,
+    });
+
+    if (!response.ok) {
+        new Notice(`❗️Failed to update Khoj content index. Ensure Khoj server connected or raise issue on Khoj Discord/Github\nError: ${response.statusText}`);
+    } else {
+        console.log(`✅ Refreshed Khoj content index. Updated: ${countOfFilesToIndex} files, Deleted: ${countOfFilesToDelete} files.`);
+    }
+
+    return files;
+}
+
 export async function configureKhojBackend(vault: Vault, setting: KhojSetting, notify: boolean = true) {
-    let vaultPath = getVaultAbsolutePath(vault);
-    let mdInVault = `${vaultPath}/**/*.md`;
-    let pdfInVault = `${vaultPath}/**/*.pdf`;
     let khojConfigUrl = `${setting.khojUrl}/api/config/data`;
 
     // Check if khoj backend is configured, note if cannot connect to backend
@@ -43,11 +103,8 @@ export async function configureKhojBackend(vault: Vault, setting: KhojSetting, n
     if (!setting.connectedToBackend) return;
 
     // Set index name from the path of the current vault
-    let indexName = vaultPath.replace(/\//g, '_').replace(/\\/g, '_').replace(/ /g, '_').replace(/:/g, '_');
     // Get default config fields from khoj backend
     let defaultConfig = await request(`${khojConfigUrl}/default`).then(response => JSON.parse(response));
-    let khojDefaultMdIndexDirectory = getIndexDirectoryFromBackendConfig(defaultConfig["content-type"]["markdown"]["embeddings-file"]);
-    let khojDefaultPdfIndexDirectory = getIndexDirectoryFromBackendConfig(defaultConfig["content-type"]["pdf"]["embeddings-file"]);
     let khojDefaultChatDirectory = getIndexDirectoryFromBackendConfig(defaultConfig["processor"]["conversation"]["conversation-logfile"]);
     let khojDefaultChatModelName = defaultConfig["processor"]["conversation"]["openai"]["chat-model"];
 
@@ -55,99 +112,7 @@ export async function configureKhojBackend(vault: Vault, setting: KhojSetting, n
     await request(khoj_already_configured ? khojConfigUrl : `${khojConfigUrl}/default`)
         .then(response => JSON.parse(response))
         .then(data => {
-            khoj_already_configured = data["content-type"] != null;
-            // If khoj backend not configured yet
-            if (!khoj_already_configured) {
-                // Create khoj content-type config with only markdown configured
-                data["content-type"] = {
-                    "markdown": {
-                        "input-filter": [mdInVault],
-                        "input-files": null,
-                        "embeddings-file": `${khojDefaultMdIndexDirectory}/${indexName}.pt`,
-                        "compressed-jsonl": `${khojDefaultMdIndexDirectory}/${indexName}.jsonl.gz`,
-                    }
-                }
-
-                const hasPdfFiles = app.vault.getFiles().some(file => file.extension === 'pdf');
-
-                if (hasPdfFiles) {
-                    data["content-type"]["pdf"] = {
-                        "input-filter": [pdfInVault],
-                        "input-files": null,
-                        "embeddings-file": `${khojDefaultPdfIndexDirectory}/${indexName}.pt`,
-                        "compressed-jsonl": `${khojDefaultPdfIndexDirectory}/${indexName}.jsonl.gz`,
-                    }
-                }
-            }
-            // Else if khoj config has no markdown content config
-            else if (!data["content-type"]["markdown"]) {
-                // Add markdown config to khoj content-type config
-                // Set markdown config to index markdown files in configured obsidian vault
-                data["content-type"]["markdown"] = {
-                    "input-filter": [mdInVault],
-                    "input-files": null,
-                    "embeddings-file": `${khojDefaultMdIndexDirectory}/${indexName}.pt`,
-                    "compressed-jsonl": `${khojDefaultMdIndexDirectory}/${indexName}.jsonl.gz`,
-                }
-            }
-            // Else if khoj is not configured to index markdown files in configured obsidian vault
-            else if (
-                data["content-type"]["markdown"]["input-files"] != null ||
-                data["content-type"]["markdown"]["input-filter"] == null ||
-                data["content-type"]["markdown"]["input-filter"].length != 1 ||
-                data["content-type"]["markdown"]["input-filter"][0] !== mdInVault) {
-                    // Update markdown config in khoj content-type config
-                    // Set markdown config to only index markdown files in configured obsidian vault
-                    let khojMdIndexDirectory = getIndexDirectoryFromBackendConfig(data["content-type"]["markdown"]["embeddings-file"]);
-                    data["content-type"]["markdown"] = {
-                        "input-filter": [mdInVault],
-                        "input-files": null,
-                        "embeddings-file": `${khojMdIndexDirectory}/${indexName}.pt`,
-                        "compressed-jsonl": `${khojMdIndexDirectory}/${indexName}.jsonl.gz`,
-                    }
-            }
-
-            if (khoj_already_configured && !data["content-type"]["pdf"]) {
-                const hasPdfFiles = app.vault.getFiles().some(file => file.extension === 'pdf');
-
-                if (hasPdfFiles) {
-                    data["content-type"]["pdf"] = {
-                        "input-filter": [pdfInVault],
-                        "input-files": null,
-                        "embeddings-file": `${khojDefaultPdfIndexDirectory}/${indexName}.pt`,
-                        "compressed-jsonl": `${khojDefaultPdfIndexDirectory}/${indexName}.jsonl.gz`,
-                    }
-                } else {
-                    data["content-type"]["pdf"] = null;
-                }
-            }
-            // Else if khoj is not configured to index pdf files in configured obsidian vault
-            else if (khoj_already_configured &&
-                (
-                    data["content-type"]["pdf"]["input-files"] != null ||
-                    data["content-type"]["pdf"]["input-filter"] == null ||
-                    data["content-type"]["pdf"]["input-filter"].length != 1 ||
-                    data["content-type"]["pdf"]["input-filter"][0] !== pdfInVault)) {
-
-                let hasPdfFiles = app.vault.getFiles().some(file => file.extension === 'pdf');
-
-                if (hasPdfFiles) {
-                    // Update pdf config in khoj content-type config
-                    // Set pdf config to only index pdf files in configured obsidian vault
-                    let khojPdfIndexDirectory = getIndexDirectoryFromBackendConfig(data["content-type"]["pdf"]["embeddings-file"]);
-                    data["content-type"]["pdf"] = {
-                        "input-filter": [pdfInVault],
-                        "input-files": null,
-                        "embeddings-file": `${khojPdfIndexDirectory}/${indexName}.pt`,
-                        "compressed-jsonl": `${khojPdfIndexDirectory}/${indexName}.jsonl.gz`,
-                    }
-                } else {
-                    data["content-type"]["pdf"] = null;
-                }
-            }
-
             let conversationLogFile = data?.["processor"]?.["conversation"]?.["conversation-logfile"] ?? `${khojDefaultChatDirectory}/conversation.json`;
-
             let processorData: ProcessorData = {
                 "conversation": {
                     "conversation-logfile": conversationLogFile,
@@ -158,9 +123,7 @@ export async function configureKhojBackend(vault: Vault, setting: KhojSetting, n
 
             // If the Open AI API Key was configured in the plugin settings
             if (!!setting.openaiApiKey) {
-
                 let openAIChatModel = data?.["processor"]?.["conversation"]?.["openai"]?.["chat-model"] ?? khojDefaultChatModelName;
-
                 processorData = {
                     "conversation": {
                         "conversation-logfile": conversationLogFile,
diff --git a/src/khoj/configure.py b/src/khoj/configure.py
index 769f015c..a67b2403 100644
--- a/src/khoj/configure.py
+++ b/src/khoj/configure.py
@@ -103,7 +103,7 @@ def configure_routes(app):
     app.mount("/static", StaticFiles(directory=constants.web_directory), name="static")
     app.include_router(api, prefix="/api")
     app.include_router(api_beta, prefix="/api/beta")
-    app.include_router(indexer, prefix="/v1/indexer")
+    app.include_router(indexer, prefix="/api/v1/index")
     app.include_router(web_client)
 
 
@@ -117,7 +117,7 @@ if not state.demo:
             state.content_index = configure_content(
                 state.content_index, state.config.content_type, all_files, state.search_models
             )
-            logger.info("📬 Content index updated via Scheduler")
+            logger.info("📪 Content index updated via Scheduler")
         except Exception as e:
             logger.error(f"🚨 Error updating content index via Scheduler: {e}", exc_info=True)
 
diff --git a/src/khoj/main.py b/src/khoj/main.py
index 6710ed05..7b1bfd7e 100644
--- a/src/khoj/main.py
+++ b/src/khoj/main.py
@@ -20,6 +20,7 @@ warnings.filterwarnings("ignore", message=r"legacy way to download files from th
 # External Packages
 import uvicorn
 from fastapi import FastAPI
+from fastapi.middleware.cors import CORSMiddleware
 from rich.logging import RichHandler
 import schedule
 
@@ -31,6 +32,15 @@ from khoj.utils.cli import cli
 # Initialize the Application Server
 app = FastAPI()
 
+# Add CORS middleware
+app.add_middleware(
+    CORSMiddleware,
+    allow_origins=["app://obsidian.md", "http://localhost:*", "https://app.khoj.dev/*", "app://khoj.dev"],
+    allow_credentials=True,
+    allow_methods=["*"],
+    allow_headers=["*"],
+)
+
 # Set Locale
 locale.setlocale(locale.LC_ALL, "")
 
diff --git a/src/khoj/processor/pdf/pdf_to_jsonl.py b/src/khoj/processor/pdf/pdf_to_jsonl.py
index 77c34617..c24d9940 100644
--- a/src/khoj/processor/pdf/pdf_to_jsonl.py
+++ b/src/khoj/processor/pdf/pdf_to_jsonl.py
@@ -65,7 +65,7 @@ class PdfToJsonl(TextToJsonl):
                 # Write the PDF file to a temporary file, as it is stored in byte format in the pdf_file object and the PyPDFLoader expects a file path
                 tmp_file = f"tmp_pdf_file.pdf"
                 with open(f"{tmp_file}", "wb") as f:
-                    bytes = base64.b64decode(pdf_files[pdf_file])
+                    bytes = pdf_files[pdf_file]
                     f.write(bytes)
                 loader = PyMuPDFLoader(f"{tmp_file}")
                 pdf_entries_per_file = [page.page_content for page in loader.load()]
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index 0331500b..7e0ab522 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -625,7 +625,7 @@ def update(
         if state.processor_config:
             components.append("Conversation processor")
         components_msg = ", ".join(components)
-        logger.info(f"📬 {components_msg} updated via API")
+        logger.info(f"📪 {components_msg} updated via API")
 
     update_telemetry_state(
         request=request,
diff --git a/src/khoj/routers/indexer.py b/src/khoj/routers/indexer.py
index f5b2b418..a09e33f5 100644
--- a/src/khoj/routers/indexer.py
+++ b/src/khoj/routers/indexer.py
@@ -1,11 +1,11 @@
 # Standard Packages
 import logging
-import sys
 from typing import Optional, Union, Dict
 
 # External Packages
-from fastapi import APIRouter, HTTPException, Header, Request, Body, Response
+from fastapi import APIRouter, HTTPException, Header, Request, Response, UploadFile
 from pydantic import BaseModel
+from khoj.routers.helpers import update_telemetry_state
 
 # Internal Packages
 from khoj.utils import state, constants
@@ -56,42 +56,30 @@ class IndexerInput(BaseModel):
     plaintext: Optional[dict[str, str]] = None
 
 
-@indexer.post("/batch")
-async def index_batch(
+@indexer.post("/update")
+async def update(
     request: Request,
+    files: list[UploadFile],
     x_api_key: str = Header(None),
-    regenerate: bool = False,
-    search_type: Optional[Union[state.SearchType, str]] = None,
+    force: bool = False,
+    t: Optional[Union[state.SearchType, str]] = None,
+    client: Optional[str] = None,
+    user_agent: Optional[str] = Header(None),
+    referer: Optional[str] = Header(None),
+    host: Optional[str] = Header(None),
 ):
     if x_api_key != "secret":
         raise HTTPException(status_code=401, detail="Invalid API Key")
     state.config_lock.acquire()
     try:
-        logger.info(f"Received batch indexing request")
-        index_batch_request_acc = b""
-        async for chunk in request.stream():
-            index_batch_request_acc += chunk
-        data_bytes = sys.getsizeof(index_batch_request_acc)
-        unit = "KB"
-        data_size = data_bytes / 1024
-        if data_size > 1000:
-            unit = "MB"
-            data_size = data_size / 1024
-        if data_size > 1000:
-            unit = "GB"
-            data_size = data_size / 1024
-        data_size_metric = f"{data_size:.2f} {unit}"
-        logger.info(f"Received {data_size_metric} of data")
-        index_batch_request = IndexBatchRequest.parse_raw(index_batch_request_acc)
-        logger.info(f"Received {len(index_batch_request.files)} files")
-
+        logger.info(f"📬 Updating content index via API call by {client}")
         org_files: Dict[str, str] = {}
         markdown_files: Dict[str, str] = {}
         pdf_files: Dict[str, str] = {}
         plaintext_files: Dict[str, str] = {}
 
-        for file in index_batch_request.files:
-            file_type = get_file_type(file.path)
+        for file in files:
+            file_type, encoding = get_file_type(file.content_type)
             dict_to_update = None
             if file_type == "org":
                 dict_to_update = org_files
@@ -103,9 +91,11 @@ async def index_batch(
                 dict_to_update = plaintext_files
 
             if dict_to_update is not None:
-                dict_to_update[file.path] = file.content
+                dict_to_update[file.filename] = (
+                    file.file.read().decode("utf-8") if encoding == "utf-8" else file.file.read()
+                )
             else:
-                logger.info(f"Skipping unsupported streamed file: {file.path}")
+                logger.warning(f"Skipped indexing unsupported file type sent by {client} client: {file.filename}")
 
         indexer_input = IndexerInput(
             org=org_files,
@@ -115,7 +105,7 @@ async def index_batch(
         )
 
         if state.config == None:
-            logger.info("First run, initializing state.")
+            logger.info("📬 Initializing content index on first run.")
             default_full_config = FullConfig(
                 content_type=None,
                 search_type=SearchConfig.parse_obj(constants.default_config["search-type"]),
@@ -142,15 +132,29 @@ async def index_batch(
             state.config.content_type,
             indexer_input.dict(),
             state.search_models,
-            regenerate=regenerate,
-            t=search_type,
+            regenerate=force,
+            t=t,
             full_corpus=False,
         )
 
     except Exception as e:
-        logger.error(f"Failed to process batch indexing request: {e}", exc_info=True)
+        logger.error(
+            f"🚨 Failed to {force} update {t} content index triggered via API call by {client}: {e}", exc_info=True
+        )
     finally:
         state.config_lock.release()
+
+    update_telemetry_state(
+        request=request,
+        telemetry_type="api",
+        api="index/update",
+        client=client,
+        user_agent=user_agent,
+        referer=referer,
+        host=host,
+    )
+
+    logger.info(f"📪 Content index updated via API call by {client}")
     return Response(content="OK", status_code=200)
 
 
diff --git a/src/khoj/utils/fs_syncer.py b/src/khoj/utils/fs_syncer.py
index 8f398104..5cf97add 100644
--- a/src/khoj/utils/fs_syncer.py
+++ b/src/khoj/utils/fs_syncer.py
@@ -210,7 +210,7 @@ def get_pdf_files(config: TextContentConfig):
     for file in all_pdf_files:
         with open(file, "rb") as f:
             try:
-                filename_to_content_map[file] = base64.b64encode(f.read()).decode("utf-8")
+                filename_to_content_map[file] = f.read()
             except Exception as e:
                 logger.warning(f"Unable to read file: {file} as PDF. Skipping file.")
                 logger.warning(e, exc_info=True)
diff --git a/src/khoj/utils/helpers.py b/src/khoj/utils/helpers.py
index f8977043..9209ff67 100644
--- a/src/khoj/utils/helpers.py
+++ b/src/khoj/utils/helpers.py
@@ -66,20 +66,25 @@ def merge_dicts(priority_dict: dict, default_dict: dict):
     return merged_dict
 
 
-def get_file_type(filepath: str) -> str:
-    "Get file type from file path"
-    file_type = Path(filepath).suffix[1:]
+def get_file_type(file_type: str) -> tuple[str, str]:
+    "Get file type from file mime type"
 
-    if file_type in ["md", "markdown"]:
-        return "markdown"
-    elif file_type in ["org", "orgmode"]:
-        return "org"
-    elif file_type in ["txt", "text", "html", "xml", "htm", "rst"]:
-        return "plaintext"
-    elif file_type in ["pdf"]:
-        return "pdf"
-
-    return file_type
+    encoding = file_type.split("=")[1].strip().lower() if ";" in file_type else None
+    file_type = file_type.split(";")[0].strip() if ";" in file_type else file_type
+    if file_type in ["text/markdown"]:
+        return "markdown", encoding
+    elif file_type in ["text/org"]:
+        return "org", encoding
+    elif file_type in ["application/pdf"]:
+        return "pdf", encoding
+    elif file_type in ["image/jpeg"]:
+        return "jpeg", encoding
+    elif file_type in ["image/png"]:
+        return "png", encoding
+    elif file_type in ["text/plain", "text/html", "application/xml", "text/x-rst"]:
+        return "plaintext", encoding
+    else:
+        return "other", encoding
 
 
 def load_model(
diff --git a/tests/test_client.py b/tests/test_client.py
index d2497f73..55bf09f7 100644
--- a/tests/test_client.py
+++ b/tests/test_client.py
@@ -6,6 +6,7 @@ from urllib.parse import quote
 
 # External Packages
 from fastapi.testclient import TestClient
+import pytest
 
 # Internal Packages
 from khoj.main import app
@@ -60,13 +61,13 @@ def test_regenerate_with_invalid_content_type(client):
 
 
 # ----------------------------------------------------------------------------------------------------
-def test_index_batch(client):
+def test_index_update(client):
     # Arrange
-    request_body = get_sample_files_data()
+    files = get_sample_files_data()
     headers = {"x-api-key": "secret"}
 
     # Act
-    response = client.post("/v1/indexer/batch", json=request_body, headers=headers)
+    response = client.post("/api/v1/index/update", files=files, headers=headers)
 
     # Assert
     assert response.status_code == 200
@@ -76,12 +77,11 @@ def test_index_batch(client):
 def test_regenerate_with_valid_content_type(client):
     for content_type in ["all", "org", "markdown", "image", "pdf", "notion", "plugin1"]:
         # Arrange
-        request_body = get_sample_files_data()
-
+        files = get_sample_files_data()
         headers = {"x-api-key": "secret"}
 
         # Act
-        response = client.post(f"/v1/indexer/batch?search_type={content_type}", json=request_body, headers=headers)
+        response = client.post(f"/api/v1/index/update?t={content_type}", files=files, headers=headers)
         # Assert
         assert response.status_code == 200, f"Returned status: {response.status_code} for content type: {content_type}"
 
@@ -92,17 +92,17 @@ def test_regenerate_with_github_fails_without_pat(client):
     response = client.get(f"/api/update?force=true&t=github")
 
     # Arrange
-    request_body = get_sample_files_data()
-
+    files = get_sample_files_data()
     headers = {"x-api-key": "secret"}
 
     # Act
-    response = client.post(f"/v1/indexer/batch?search_type=github", json=request_body, headers=headers)
+    response = client.post(f"/api/v1/index/update?t=github", files=files, headers=headers)
     # Assert
     assert response.status_code == 200, f"Returned status: {response.status_code} for content type: github"
 
 
 # ----------------------------------------------------------------------------------------------------
+@pytest.mark.skip(reason="Flaky test on parallel test runs")
 def test_get_configured_types_via_api(client):
     # Act
     response = client.get(f"/api/config/types")
@@ -288,24 +288,20 @@ def test_notes_search_with_exclude_filter(
 
 def get_sample_files_data():
     return {
-        "org": {
-            "path/to/filename.org": "* practicing piano",
-            "path/to/filename1.org": "** top 3 reasons why I moved to SF",
-            "path/to/filename2.org": "* how to build a search engine",
-        },
-        "pdf": {
-            "path/to/filename.pdf": "Moore's law does not apply to consumer hardware",
-            "path/to/filename1.pdf": "The sun is a ball of helium",
-            "path/to/filename2.pdf": "Effect of sunshine on baseline human happiness",
-        },
-        "plaintext": {
-            "path/to/filename.txt": "data,column,value",
-            "path/to/filename1.txt": "<html>my first web page</html>",
-            "path/to/filename2.txt": "2021-02-02 Journal Entry",
-        },
-        "markdown": {
-            "path/to/filename.md": "# Notes from client call",
-            "path/to/filename1.md": "## Studying anthropological records from the Fatimid caliphate",
-            "path/to/filename2.md": "**Understanding science through the lens of art**",
-        },
+        "files": ("path/to/filename.org", "* practicing piano", "text/org"),
+        "files": ("path/to/filename1.org", "** top 3 reasons why I moved to SF", "text/org"),
+        "files": ("path/to/filename2.org", "* how to build a search engine", "text/org"),
+        "files": ("path/to/filename.pdf", "Moore's law does not apply to consumer hardware", "application/pdf"),
+        "files": ("path/to/filename1.pdf", "The sun is a ball of helium", "application/pdf"),
+        "files": ("path/to/filename2.pdf", "Effect of sunshine on baseline human happiness", "application/pdf"),
+        "files": ("path/to/filename.txt", "data,column,value", "text/plain"),
+        "files": ("path/to/filename1.txt", "<html>my first web page</html>", "text/plain"),
+        "files": ("path/to/filename2.txt", "2021-02-02 Journal Entry", "text/plain"),
+        "files": ("path/to/filename.md", "# Notes from client call", "text/markdown"),
+        "files": (
+            "path/to/filename1.md",
+            "## Studying anthropological records from the Fatimid caliphate",
+            "text/markdown",
+        ),
+        "files": ("path/to/filename2.md", "**Understanding science through the lens of art**", "text/markdown"),
     }
diff --git a/tests/test_pdf_to_jsonl.py b/tests/test_pdf_to_jsonl.py
index bacce37c..b9b26986 100644
--- a/tests/test_pdf_to_jsonl.py
+++ b/tests/test_pdf_to_jsonl.py
@@ -1,7 +1,6 @@
 # Standard Packages
 import json
 import os
-import base64
 
 # Internal Packages
 from khoj.processor.pdf.pdf_to_jsonl import PdfToJsonl
@@ -16,7 +15,7 @@ def test_single_page_pdf_to_jsonl():
     # Extract Entries from specified Pdf files
     # Read singlepage.pdf into memory as bytes
     with open("tests/data/pdf/singlepage.pdf", "rb") as f:
-        pdf_bytes = base64.b64encode(f.read()).decode("utf-8")
+        pdf_bytes = f.read()
 
     data = {"tests/data/pdf/singlepage.pdf": pdf_bytes}
     entries, entry_to_file_map = PdfToJsonl.extract_pdf_entries(pdf_files=data)
@@ -36,7 +35,7 @@ def test_multi_page_pdf_to_jsonl():
     # Act
     # Extract Entries from specified Pdf files
     with open("tests/data/pdf/multipage.pdf", "rb") as f:
-        pdf_bytes = base64.b64encode(f.read()).decode("utf-8")
+        pdf_bytes = f.read()
 
     data = {"tests/data/pdf/multipage.pdf": pdf_bytes}
     entries, entry_to_file_map = PdfToJsonl.extract_pdf_entries(pdf_files=data)