diff --git a/apps/web/components/common/file-upload-button.tsx b/apps/web/components/common/file-upload-button.tsx
index 1c1ddc37..a52bd1dc 100644
--- a/apps/web/components/common/file-upload-button.tsx
+++ b/apps/web/components/common/file-upload-button.tsx
@@ -3,33 +3,28 @@
 import { useRef } from "react";
 import { Paperclip } from "lucide-react";
 import { cn } from "@/lib/utils";
-import type { UploadResult } from "@/shared/hooks/use-file-upload";
 
 interface FileUploadButtonProps {
-  onUpload: (file: File) => Promise<UploadResult | null>;
-  onInsert?: (result: UploadResult, isImage: boolean) => void;
+  /** Called with the selected File — caller handles upload. */
+  onSelect: (file: File) => void;
   disabled?: boolean;
   className?: string;
   size?: "sm" | "default";
 }
 
 function FileUploadButton({
-  onUpload,
-  onInsert,
+  onSelect,
   disabled,
   className,
   size = "default",
 }: FileUploadButtonProps) {
   const inputRef = useRef<HTMLInputElement>(null);
 
-  const handleChange = async (e: React.ChangeEvent<HTMLInputElement>) => {
+  const handleChange = (e: React.ChangeEvent<HTMLInputElement>) => {
     const file = e.target.files?.[0];
     if (!file) return;
     e.target.value = "";
-    const result = await onUpload(file);
-    if (result && onInsert) {
-      onInsert(result, file.type.startsWith("image/"));
-    }
+    onSelect(file);
   };
 
   const iconSize = size === "sm" ? "h-3.5 w-3.5" : "h-4 w-4";
diff --git a/apps/web/components/common/rich-text-editor.css b/apps/web/components/common/rich-text-editor.css
index faa3bb16..5a0a9ba7 100644
--- a/apps/web/components/common/rich-text-editor.css
+++ b/apps/web/components/common/rich-text-editor.css
@@ -235,8 +235,8 @@
   display: inline;
 }
 
-/* Images in readonly mode */
-.rich-text-editor.readonly img {
+/* Images — shared styling for both editing and readonly */
+.rich-text-editor img {
   border-radius: var(--radius);
   margin: 0.5rem 0;
 }
diff --git a/apps/web/components/common/rich-text-editor.tsx b/apps/web/components/common/rich-text-editor.tsx
index c9cf9135..fbdd862c 100644
--- a/apps/web/components/common/rich-text-editor.tsx
+++ b/apps/web/components/common/rich-text-editor.tsx
@@ -47,7 +47,8 @@ interface RichTextEditorRef {
   getMarkdown: () => string;
   clearContent: () => void;
   focus: () => void;
-  insertFile: (filename: string, url: string, isImage: boolean) => void;
+  /** Upload a file and insert it into the editor (blob preview → upload → replace). */
+  uploadFile: (file: File) => void;
 }
 
 const LinkExtension = Link.extend({ inclusive: false }).configure({
@@ -133,6 +134,64 @@ function removeImageBySrc(editor: ReturnType<typeof useEditor>, src: string) {
   if (deleted) editor.view.dispatch(tr);
 }
 
+/**
+ * Shared upload flow: insert blob preview → upload → replace with real URL.
+ * Used by both paste/drop (at cursor) and button upload (at end of doc).
+ */
+async function uploadAndInsertFile(
+  // eslint-disable-next-line @typescript-eslint/no-explicit-any
+  editor: any,
+  file: File,
+  handler: (file: File) => Promise<UploadResult | null>,
+  pos?: number,
+) {
+  const isImage = file.type.startsWith("image/");
+
+  if (isImage) {
+    const blobUrl = URL.createObjectURL(file);
+    const imgAttrs = { src: blobUrl, alt: file.name, uploading: true };
+    if (pos !== undefined) {
+      editor.chain().focus().insertContentAt(pos, { type: "image", attrs: imgAttrs }).run();
+    } else {
+      editor.chain().focus().setImage(imgAttrs).run();
+    }
+
+    try {
+      const result = await handler(file);
+      if (result) {
+        const { tr } = editor.state;
+        editor.state.doc.descendants((node: { type: { name: string }; attrs: { src: string } }, nodePos: number) => {
+          if (node.type.name === "image" && node.attrs.src === blobUrl) {
+            tr.setNodeMarkup(nodePos, undefined, {
+              ...node.attrs,
+              src: result.link,
+              alt: result.filename,
+              uploading: false,
+            });
+          }
+        });
+        editor.view.dispatch(tr);
+      } else {
+        removeImageBySrc(editor, blobUrl);
+      }
+    } catch {
+      removeImageBySrc(editor, blobUrl);
+    } finally {
+      URL.revokeObjectURL(blobUrl);
+    }
+  } else {
+    // Non-image: upload first, then insert link
+    const result = await handler(file);
+    if (!result) return;
+    const linkText = `[${result.filename}](${result.link})`;
+    if (pos !== undefined) {
+      editor.chain().focus().insertContentAt(pos, linkText).run();
+    } else {
+      editor.chain().focus().insertContent(linkText).run();
+    }
+  }
+}
+
 function createFileUploadExtension(
   onUploadFileRef: React.RefObject<((file: File) => Promise<UploadResult | null>) | undefined>,
 ) {
@@ -141,65 +200,13 @@ function createFileUploadExtension(
     addProseMirrorPlugins() {
       const { editor } = this;
 
-      const handleFiles = async (files: FileList, pos?: number) => {
+      const handleFiles = async (files: FileList) => {
         const handler = onUploadFileRef.current;
         if (!handler) return false;
-
-        let handled = false;
         for (const file of Array.from(files)) {
-          handled = true;
-          const isImage = file.type.startsWith("image/");
-
-          if (isImage) {
-            // Instant preview via blob URL with uploading flag for CSS styling
-            const blobUrl = URL.createObjectURL(file);
-            const imgAttrs = { src: blobUrl, alt: file.name, uploading: true };
-            if (pos !== undefined) {
-              editor.chain().focus().insertContentAt(pos, { type: "image", attrs: imgAttrs }).run();
-            } else {
-              editor.chain().focus().setImage(imgAttrs).run();
-            }
-
-            try {
-              const result = await handler(file);
-              if (result) {
-                const { tr } = editor.state;
-                editor.state.doc.descendants((node, nodePos) => {
-                  if (node.type.name === "image" && node.attrs.src === blobUrl) {
-                    tr.setNodeMarkup(nodePos, undefined, {
-                      ...node.attrs,
-                      src: result.link,
-                      alt: result.filename,
-                      uploading: false,
-                    });
-                  }
-                });
-                editor.view.dispatch(tr);
-              } else {
-                removeImageBySrc(editor, blobUrl);
-              }
-            } catch {
-              removeImageBySrc(editor, blobUrl);
-            } finally {
-              URL.revokeObjectURL(blobUrl);
-            }
-          } else {
-            // Non-image: upload first, then insert link
-            try {
-              const result = await handler(file);
-              if (!result) continue;
-              const linkText = `[${result.filename}](${result.link})`;
-              if (pos !== undefined) {
-                editor.chain().focus().insertContentAt(pos, linkText).run();
-              } else {
-                editor.chain().focus().insertContent(linkText).run();
-              }
-            } catch {
-              // Upload errors handled by the hook/caller via toast
-            }
-          }
+          await uploadAndInsertFile(editor, file, handler);
         }
-        return handled;
+        return true;
       };
 
       return [
@@ -386,13 +393,11 @@ const RichTextEditor = forwardRef<RichTextEditorRef, RichTextEditorProps>(
       focus: () => {
         editor?.commands.focus();
       },
-      insertFile: (filename: string, url: string, isImage: boolean) => {
-        if (!editor) return;
-        if (isImage) {
-          editor.chain().focus().setImage({ src: url, alt: filename }).run();
-        } else {
-          editor.chain().focus().insertContent(`[${filename}](${url})`).run();
-        }
+      uploadFile: (file: File) => {
+        if (!editor || !onUploadFileRef.current) return;
+        // Insert at end of doc to avoid replacing selection
+        const endPos = editor.state.doc.content.size;
+        uploadAndInsertFile(editor, file, onUploadFileRef.current, endPos);
       },
     }));
 
diff --git a/apps/web/features/issues/components/comment-card.tsx b/apps/web/features/issues/components/comment-card.tsx
index 7b2fd7de..110a7041 100644
--- a/apps/web/features/issues/components/comment-card.tsx
+++ b/apps/web/features/issues/components/comment-card.tsx
@@ -228,14 +228,14 @@ function CommentRow({
               defaultValue={entry.content ?? ""}
               placeholder="Edit comment..."
               onSubmit={saveEdit}
+              onUploadFile={(file) => uploadWithToast(file, { issueId })}
               debounceMs={100}
             />
           </div>
           <div className="flex items-center justify-between mt-2">
             <FileUploadButton
               size="sm"
-              onUpload={(file) => uploadWithToast(file, { issueId })}
-              onInsert={(result, isImage) => editEditorRef.current?.insertFile(result.filename, result.link, isImage)}
+              onSelect={(file) => editEditorRef.current?.uploadFile(file)}
             />
             <div className="flex items-center gap-2">
               <Button size="sm" variant="ghost" onClick={cancelEdit}>Cancel</Button>
@@ -441,8 +441,7 @@ function CommentCard({
                 <div className="flex items-center justify-between mt-2">
                   <FileUploadButton
                     size="sm"
-                    onUpload={(file) => uploadWithToast(file, { issueId })}
-                    onInsert={(result, isImage) => editEditorRef.current?.insertFile(result.filename, result.link, isImage)}
+                    onSelect={(file) => editEditorRef.current?.uploadFile(file)}
                   />
                   <div className="flex items-center gap-2">
                     <Button size="sm" variant="ghost" onClick={cancelEdit}>Cancel</Button>
diff --git a/apps/web/features/issues/components/comment-input.tsx b/apps/web/features/issues/components/comment-input.tsx
index 08bf934d..b3162fac 100644
--- a/apps/web/features/issues/components/comment-input.tsx
+++ b/apps/web/features/issues/components/comment-input.tsx
@@ -14,15 +14,12 @@ interface CommentInputProps {
 
 function CommentInput({ issueId, onSubmit }: CommentInputProps) {
   const editorRef = useRef<RichTextEditorRef>(null);
-  const attachmentIdsRef = useRef<string[]>([]);
   const [isEmpty, setIsEmpty] = useState(true);
   const [submitting, setSubmitting] = useState(false);
-  const { uploadWithToast, uploading } = useFileUpload();
+  const { uploadWithToast } = useFileUpload();
 
   const handleUpload = async (file: File) => {
-    const result = await uploadWithToast(file, { issueId });
-    if (result) attachmentIdsRef.current.push(result.id);
-    return result;
+    return await uploadWithToast(file, { issueId });
   };
 
   const handleSubmit = async () => {
@@ -30,10 +27,8 @@ function CommentInput({ issueId, onSubmit }: CommentInputProps) {
     if (!content || submitting) return;
     setSubmitting(true);
     try {
-      const ids = attachmentIdsRef.current.length > 0 ? [...attachmentIdsRef.current] : undefined;
-      await onSubmit(content, ids);
+      await onSubmit(content);
       editorRef.current?.clearContent();
-      attachmentIdsRef.current = [];
       setIsEmpty(true);
     } finally {
       setSubmitting(false);
@@ -55,11 +50,7 @@ function CommentInput({ issueId, onSubmit }: CommentInputProps) {
       <div className="absolute bottom-1 right-1.5 flex items-center gap-1">
         <FileUploadButton
           size="sm"
-          onUpload={handleUpload}
-          onInsert={(result, isImage) =>
-            editorRef.current?.insertFile(result.filename, result.link, isImage)
-          }
-          disabled={uploading}
+          onSelect={(file) => editorRef.current?.uploadFile(file)}
         />
         <Button
           size="icon-xs"
diff --git a/apps/web/features/issues/components/issue-detail.tsx b/apps/web/features/issues/components/issue-detail.tsx
index 3c573d61..742db74c 100644
--- a/apps/web/features/issues/components/issue-detail.tsx
+++ b/apps/web/features/issues/components/issue-detail.tsx
@@ -667,8 +667,7 @@ export function IssueDetail({ issueId, onDelete, defaultSidebarOpen = true, layo
             )}
             <FileUploadButton
               size="sm"
-              onUpload={handleDescriptionUpload}
-              onInsert={(result, isImage) => descEditorRef.current?.insertFile(result.filename, result.link, isImage)}
+              onSelect={(file) => descEditorRef.current?.uploadFile(file)}
             />
           </div>
 
diff --git a/apps/web/features/issues/components/reply-input.tsx b/apps/web/features/issues/components/reply-input.tsx
index e3fd5da8..d5125303 100644
--- a/apps/web/features/issues/components/reply-input.tsx
+++ b/apps/web/features/issues/components/reply-input.tsx
@@ -35,11 +35,10 @@ function ReplyInput({
 }: ReplyInputProps) {
   const editorRef = useRef<RichTextEditorRef>(null);
   const measureRef = useRef<HTMLDivElement>(null);
-  const attachmentIdsRef = useRef<string[]>([]);
   const [isEmpty, setIsEmpty] = useState(true);
   const [isExpanded, setIsExpanded] = useState(false);
   const [submitting, setSubmitting] = useState(false);
-  const { uploadWithToast, uploading } = useFileUpload();
+  const { uploadWithToast } = useFileUpload();
 
   useEffect(() => {
     const el = measureRef.current;
@@ -53,9 +52,7 @@ function ReplyInput({
   }, []);
 
   const handleUpload = async (file: File) => {
-    const result = await uploadWithToast(file, { issueId });
-    if (result) attachmentIdsRef.current.push(result.id);
-    return result;
+    return await uploadWithToast(file, { issueId });
   };
 
   const handleSubmit = async () => {
@@ -63,10 +60,8 @@ function ReplyInput({
     if (!content || submitting) return;
     setSubmitting(true);
     try {
-      const ids = attachmentIdsRef.current.length > 0 ? [...attachmentIdsRef.current] : undefined;
-      await onSubmit(content, ids);
+      await onSubmit(content);
       editorRef.current?.clearContent();
-      attachmentIdsRef.current = [];
       setIsEmpty(true);
     } finally {
       setSubmitting(false);
@@ -105,11 +100,7 @@ function ReplyInput({
         <div className="absolute bottom-0 right-0 flex items-center gap-1 text-muted-foreground transition-colors group-focus-within/editor:text-foreground">
           <FileUploadButton
             size="sm"
-            onUpload={handleUpload}
-            onInsert={(result, isImage) =>
-              editorRef.current?.insertFile(result.filename, result.link, isImage)
-            }
-            disabled={uploading}
+            onSelect={(file) => editorRef.current?.uploadFile(file)}
           />
           <button
             type="button"
diff --git a/apps/web/features/modals/create-issue.tsx b/apps/web/features/modals/create-issue.tsx
index 67ac07c3..df8252df 100644
--- a/apps/web/features/modals/create-issue.tsx
+++ b/apps/web/features/modals/create-issue.tsx
@@ -419,8 +419,7 @@ export function CreateIssueModal({ onClose, data }: { onClose: () => void; data?
         {/* Footer */}
         <div className="flex items-center justify-between px-4 py-3 border-t shrink-0">
           <FileUploadButton
-            onUpload={handleUpload}
-            onInsert={(result, isImage) => descEditorRef.current?.insertFile(result.filename, result.link, isImage)}
+            onSelect={(file) => descEditorRef.current?.uploadFile(file)}
           />
           <Button size="sm" onClick={handleSubmit} disabled={!title.trim() || submitting}>
             {submitting ? "Creating..." : "Create Issue"}