diff --git a/app/components/Editor.tsx b/app/components/Editor.tsx
index c5f3e41bd..2fb0c45f0 100644
--- a/app/components/Editor.tsx
+++ b/app/components/Editor.tsx
@@ -50,7 +50,7 @@ export type Props = Optional<
   previewsDisabled?: boolean;
   onHeadingsChange?: (headings: Heading[]) => void;
   onSynced?: () => Promise<void>;
-  onPublish?: (event: React.MouseEvent) => any;
+  onPublish?: (event: React.MouseEvent) => void;
   editorStyle?: React.CSSProperties;
 };
 
@@ -138,7 +138,7 @@ function Editor(props: Props, ref: React.RefObject<SharedEditor> | null) {
             : 1
       );
     },
-    [documents]
+    [locale, documents]
   );
 
   const handleUploadFile = React.useCallback(
diff --git a/app/editor/index.tsx b/app/editor/index.tsx
index 9bd1218a9..9d98cb318 100644
--- a/app/editor/index.tsx
+++ b/app/editor/index.tsx
@@ -23,6 +23,7 @@ import {
 import { Decoration, EditorView, NodeViewConstructor } from "prosemirror-view";
 import * as React from "react";
 import styled, { css, DefaultTheme, ThemeProps } from "styled-components";
+import insertFiles from "@shared/editor/commands/insertFiles";
 import Styles from "@shared/editor/components/Styles";
 import { EmbedDescriptor } from "@shared/editor/embeds";
 import Extension, { CommandFactory } from "@shared/editor/lib/Extension";
@@ -584,6 +585,25 @@ export class Editor extends React.PureComponent<
     window?.getSelection()?.removeAllRanges();
   };
 
+  /**
+   * Insert files at the current selection.
+   * =
+   * @param event The source event
+   * @param files The files to insert
+   * @returns True if the files were inserted
+   */
+  public insertFiles = (
+    event: React.ChangeEvent<HTMLInputElement>,
+    files: File[]
+  ) =>
+    insertFiles(
+      this.view,
+      event,
+      this.view.state.selection.to,
+      files,
+      this.props
+    );
+
   /**
    * Returns true if the trimmed content of the editor is an empty string.
    *
diff --git a/app/scenes/Document/components/CommentForm.tsx b/app/scenes/Document/components/CommentForm.tsx
index bde685bb6..6eae5663d 100644
--- a/app/scenes/Document/components/CommentForm.tsx
+++ b/app/scenes/Document/components/CommentForm.tsx
@@ -1,16 +1,22 @@
 import { m } from "framer-motion";
 import { action } from "mobx";
 import { observer } from "mobx-react";
+import { ImageIcon } from "outline-icons";
 import * as React from "react";
 import { useTranslation } from "react-i18next";
+import { VisuallyHidden } from "reakit";
 import { toast } from "sonner";
+import { useTheme } from "styled-components";
 import { v4 as uuidv4 } from "uuid";
-import { CommentValidation } from "@shared/validations";
+import { getEventFiles } from "@shared/utils/files";
+import { AttachmentValidation, CommentValidation } from "@shared/validations";
 import Comment from "~/models/Comment";
 import Avatar from "~/components/Avatar";
 import ButtonSmall from "~/components/ButtonSmall";
 import { useDocumentContext } from "~/components/DocumentContext";
 import Flex from "~/components/Flex";
+import NudeButton from "~/components/NudeButton";
+import Tooltip from "~/components/Tooltip";
 import type { Editor as SharedEditor } from "~/editor";
 import useCurrentUser from "~/hooks/useCurrentUser";
 import useOnClickOutside from "~/hooks/useOnClickOutside";
@@ -64,6 +70,8 @@ function CommentForm({
   const editorRef = React.useRef<SharedEditor>(null);
   const [forceRender, setForceRender] = React.useState(0);
   const [inputFocused, setInputFocused] = React.useState(autoFocus);
+  const file = React.useRef<HTMLInputElement>(null);
+  const theme = useTheme();
   const { t } = useTranslation();
   const { comments } = useStores();
   const user = useCurrentUser();
@@ -188,6 +196,23 @@ function CommentForm({
     onBlur?.();
   };
 
+  const handleFilePicked = (event: React.ChangeEvent<HTMLInputElement>) => {
+    event.stopPropagation();
+    event.preventDefault();
+
+    const files = getEventFiles(event);
+    if (!files.length) {
+      return;
+    }
+    editorRef.current?.insertFiles(event, files);
+  };
+
+  const handleImageUpload = (event: React.MouseEvent<HTMLButtonElement>) => {
+    event.stopPropagation();
+    event.preventDefault();
+    file.current?.click();
+  };
+
   // Focus the editor when it's a new comment just mounted, after a delay as the
   // editor is mounted within a fade transition.
   React.useEffect(() => {
@@ -227,6 +252,15 @@ function CommentForm({
       {...presence}
       {...rest}
     >
+      <VisuallyHidden>
+        <input
+          ref={file}
+          type="file"
+          onChange={handleFilePicked}
+          accept={AttachmentValidation.imageContentTypes.join(", ")}
+          tabIndex={-1}
+        />
+      </VisuallyHidden>
       <Flex gap={8} align="flex-start" reverse={dir === "rtl"}>
         <Avatar model={user} size={24} style={{ marginTop: 8 }} />
         <Bubble
@@ -256,13 +290,20 @@ function CommentForm({
             }
           />
           {(inputFocused || data) && (
-            <Flex justify={dir === "rtl" ? "flex-end" : "flex-start"} gap={8}>
-              <ButtonSmall type="submit" borderOnHover>
-                {thread && !thread.isNew ? t("Reply") : t("Post")}
-              </ButtonSmall>
-              <ButtonSmall onClick={handleCancel} neutral borderOnHover>
-                {t("Cancel")}
-              </ButtonSmall>
+            <Flex justify="space-between" reverse={dir === "rtl"} gap={8}>
+              <Flex gap={8}>
+                <ButtonSmall type="submit" borderOnHover>
+                  {thread && !thread.isNew ? t("Reply") : t("Post")}
+                </ButtonSmall>
+                <ButtonSmall onClick={handleCancel} neutral borderOnHover>
+                  {t("Cancel")}
+                </ButtonSmall>
+              </Flex>
+              <Tooltip delay={500} tooltip={t("Upload image")} placement="top">
+                <NudeButton onClick={handleImageUpload}>
+                  <ImageIcon color={theme.textTertiary} />
+                </NudeButton>
+              </Tooltip>
             </Flex>
           )}
         </Bubble>
diff --git a/shared/i18n/locales/en_US/translation.json b/shared/i18n/locales/en_US/translation.json
index 10be81c4b..07671e2e1 100644
--- a/shared/i18n/locales/en_US/translation.json
+++ b/shared/i18n/locales/en_US/translation.json
@@ -500,6 +500,7 @@
   "Reply": "Reply",
   "Post": "Post",
   "Cancel": "Cancel",
+  "Upload image": "Upload image",
   "No comments yet": "No comments yet",
   "Error updating comment": "Error updating comment",
   "Images are still uploading.\nAre you sure you want to discard them?": "Images are still uploading.\nAre you sure you want to discard them?",