diff --git a/refact-agent/gui/src/components/ChatForm/ChatControls.tsx b/refact-agent/gui/src/components/ChatForm/ChatControls.tsx
index dcb009663..b897ac364 100644
--- a/refact-agent/gui/src/components/ChatForm/ChatControls.tsx
+++ b/refact-agent/gui/src/components/ChatForm/ChatControls.tsx
@@ -8,6 +8,7 @@ import {
   Box,
   Switch,
   Badge,
+  Button,
 } from "@radix-ui/themes";
 import { Select } from "../Select";
 import { type Config } from "../../features/Config/configSlice";
@@ -36,6 +37,7 @@ import {
   setToolUse,
 } from "../../features/Chat/Thread";
 import { useAppSelector, useAppDispatch, useCapsForToolUse } from "../../hooks";
+import { useAttachedFiles } from "./useCheckBoxes";
 
 export const ApplyPatchSwitch: React.FC = () => {
   const dispatch = useAppDispatch();
@@ -223,6 +225,7 @@ export type ChatControlsProps = {
   ) => void;
 
   host: Config["host"];
+  attachedFiles: ReturnType<typeof useAttachedFiles>;
 };
 
 const ChatControlCheckBox: React.FC<{
@@ -294,6 +297,7 @@ export const ChatControls: React.FC<ChatControlsProps> = ({
   checkboxes,
   onCheckedChange,
   host,
+  attachedFiles,
 }) => {
   const refs = useTourRefs();
   const dispatch = useAppDispatch();
@@ -343,6 +347,18 @@ export const ChatControls: React.FC<ChatControlsProps> = ({
         );
       })}
 
+      {host !== "web" && (
+        <Button
+          title="Attach current file"
+          onClick={attachedFiles.addFile}
+          disabled={!attachedFiles.activeFile.name || attachedFiles.attached}
+          size="1"
+          radius="medium"
+        >
+          Attach: {attachedFiles.activeFile.name}
+        </Button>
+      )}
+
       {showControls && (
         <Flex gap="2" direction="column">
           <ToolUseSwitch
diff --git a/refact-agent/gui/src/components/ChatForm/ChatForm.test.tsx b/refact-agent/gui/src/components/ChatForm/ChatForm.test.tsx
index 5cc1a32eb..6e47cdcb7 100644
--- a/refact-agent/gui/src/components/ChatForm/ChatForm.test.tsx
+++ b/refact-agent/gui/src/components/ChatForm/ChatForm.test.tsx
@@ -115,11 +115,7 @@ describe("ChatForm", () => {
     await user.type(textarea, "foo");
     await user.keyboard("{Enter}");
     const markdown = "```python\nprint(1)\n```\n";
-    const cursor = app.store.getState().active_file.cursor;
-
-    const expected = `@file foo.txt:${
-      cursor ? cursor + 1 : 1
-    }\n${markdown}\nfoo\n`;
+    const expected = `${markdown}\nfoo\n`;
     expect(fakeOnSubmit).toHaveBeenCalledWith(expected);
   });
 
diff --git a/refact-agent/gui/src/components/ChatForm/ChatForm.tsx b/refact-agent/gui/src/components/ChatForm/ChatForm.tsx
index eb689f8c6..11e048ee0 100644
--- a/refact-agent/gui/src/components/ChatForm/ChatForm.tsx
+++ b/refact-agent/gui/src/components/ChatForm/ChatForm.tsx
@@ -19,7 +19,6 @@ import {
   useSendChatRequest,
   useCompressChat,
   useAutoFocusOnce,
-  // useTotalTokenUsage,
 } from "../../hooks";
 import { ErrorCallout, Callout } from "../Callout";
 import { ComboBox } from "../ComboBox";
@@ -30,17 +29,16 @@ import { useCommandCompletionAndPreviewFiles } from "./useCommandCompletionAndPr
 import { useAppSelector, useAppDispatch } from "../../hooks";
 import { clearError, getErrorMessage } from "../../features/Errors/errorsSlice";
 import { useTourRefs } from "../../features/Tour";
-import { useCheckboxes } from "./useCheckBoxes";
+import { useAttachedFiles, useCheckboxes } from "./useCheckBoxes";
 import { useInputValue } from "./useInputValue";
 import {
   clearInformation,
   getInformationMessage,
-  // setInformation,
 } from "../../features/Errors/informationSlice";
 import { InformationCallout } from "../Callout/Callout";
 import { ToolConfirmation } from "./ToolConfirmation";
 import { getPauseReasonsWithPauseStatus } from "../../features/ToolConfirmation/confirmationSlice";
-import { AttachFileButton, FileList } from "../Dropzone";
+import { AttachImagesButton, FileList } from "../Dropzone";
 import { useAttachedImages } from "../../hooks/useAttachedImages";
 import {
   enableSend,
@@ -51,7 +49,6 @@ import {
   selectLastSentCompression,
   selectMessages,
   selectPreventSend,
-  // selectThreadMaximumTokens,
   selectThreadToolUse,
   selectToolUse,
 } from "../../features/Chat";
@@ -59,7 +56,6 @@ import { telemetryApi } from "../../services/refact";
 import { push } from "../../features/Pages/pagesSlice";
 import { AgentCapabilities } from "./AgentCapabilities";
 import { TokensPreview } from "./TokensPreview";
-// import { useUsageCounter } from "../UsageCounter/useUsageCounter";
 import classNames from "classnames";
 import { ArchiveIcon } from "@radix-ui/react-icons";
 
@@ -97,6 +93,7 @@ export const ChatForm: React.FC<ChatFormProps> = ({
   const lastSentCompression = useAppSelector(selectLastSentCompression);
   const { compressChat, compressChatRequest } = useCompressChat();
   const autoFocus = useAutoFocusOnce();
+  const attachedFiles = useAttachedFiles();
 
   const shouldAgentCapabilitiesBeShown = useMemo(() => {
     return threadToolUse === "agent";
@@ -161,7 +158,6 @@ export const ChatForm: React.FC<ChatFormProps> = ({
     checkboxes,
     onToggleCheckbox,
     unCheckAll,
-    setFileInteracted,
     setLineSelectionInteracted,
   } = useCheckboxes();
 
@@ -184,21 +180,23 @@ export const ChatForm: React.FC<ChatFormProps> = ({
   const handleSubmit = useCallback(() => {
     const trimmedValue = value.trim();
     if (!disableSend && trimmedValue.length > 0) {
+      const valueWithFiles = attachedFiles.addFilesToInput(trimmedValue);
       const valueIncludingChecks = addCheckboxValuesToInput(
-        trimmedValue,
+        valueWithFiles,
         checkboxes,
       );
-      setFileInteracted(false);
+      // TODO: add @files
       setLineSelectionInteracted(false);
       onSubmit(valueIncludingChecks);
       setValue(() => "");
       unCheckAll();
+      attachedFiles.removeAll();
     }
   }, [
     value,
     disableSend,
+    attachedFiles,
     checkboxes,
-    setFileInteracted,
     setLineSelectionInteracted,
     onSubmit,
     setValue,
@@ -241,7 +239,6 @@ export const ChatForm: React.FC<ChatFormProps> = ({
       setValue(command);
       const trimmedCommand = command.trim();
       if (!trimmedCommand) {
-        setFileInteracted(false);
         setLineSelectionInteracted(false);
       }
 
@@ -251,7 +248,7 @@ export const ChatForm: React.FC<ChatFormProps> = ({
         handleHelpInfo(null);
       }
     },
-    [handleHelpInfo, setValue, setFileInteracted, setLineSelectionInteracted],
+    [handleHelpInfo, setValue, setLineSelectionInteracted],
   );
 
   const handleAgentIntegrationsClick = useCallback(() => {
@@ -423,7 +420,9 @@ export const ChatForm: React.FC<ChatFormProps> = ({
                 />
               )}
               {config.features?.images !== false &&
-                isMultimodalitySupportedForCurrentModel && <AttachFileButton />}
+                isMultimodalitySupportedForCurrentModel && (
+                  <AttachImagesButton />
+                )}
               {/* TODO: Reserved space for microphone button coming later on */}
               <PaperPlaneButton
                 disabled={disableSend}
@@ -435,12 +434,14 @@ export const ChatForm: React.FC<ChatFormProps> = ({
           </Flex>
         </Form>
       </Flex>
-      <FileList />
+      <FileList attachedFiles={attachedFiles} />
 
       <ChatControls
+        // handle adding files
         host={config.host}
         checkboxes={checkboxes}
         onCheckedChange={onToggleCheckbox}
+        attachedFiles={attachedFiles}
       />
     </Card>
   );
diff --git a/refact-agent/gui/src/components/ChatForm/useCheckBoxes.ts b/refact-agent/gui/src/components/ChatForm/useCheckBoxes.ts
index c9c7ea7f6..7727c0e99 100644
--- a/refact-agent/gui/src/components/ChatForm/useCheckBoxes.ts
+++ b/refact-agent/gui/src/components/ChatForm/useCheckBoxes.ts
@@ -1,93 +1,99 @@
 import { useState, useMemo, useCallback, useEffect } from "react";
 import { selectSelectedSnippet } from "../../features/Chat/selectedSnippet";
-import { selectActiveFile } from "../../features/Chat/activeFile";
+import { FileInfo, selectActiveFile } from "../../features/Chat/activeFile";
 import { useConfig, useAppSelector } from "../../hooks";
 import type { Checkbox } from "./ChatControls";
-import {
-  selectIsStreaming,
-  selectMessages,
-} from "../../features/Chat/Thread/selectors";
+import { selectMessages } from "../../features/Chat/Thread/selectors";
 import { createSelector } from "@reduxjs/toolkit";
-
-const shouldShowSelector = createSelector(
-  [selectMessages, selectIsStreaming],
-  (messages, isStreaming) => {
-    return messages.length === 0 && !isStreaming;
-  },
-);
+import { filename } from "../../utils";
+import { ideAttachFileToChat } from "../../hooks";
 
 const messageLengthSelector = createSelector(
   [selectMessages],
   (messages) => messages.length,
 );
 
-const useAttachActiveFile = (
-  interacted: boolean,
-  hasSnippet: boolean,
-): [Checkbox, () => void] => {
+// TODO: add ide event here.
+
+export function useAttachedFiles() {
+  const [files, setFiles] = useState<FileInfo[]>([]);
   const activeFile = useAppSelector(selectActiveFile);
-  const shouldShow = useAppSelector(shouldShowSelector);
-  const messageLength = useAppSelector(messageLengthSelector);
 
-  const filePathWithLines = useMemo(() => {
-    const hasLines = activeFile.line1 !== null && activeFile.line2 !== null;
-
-    if (!hasLines) return activeFile.path;
-    return `${activeFile.path}:${
-      activeFile.cursor ? activeFile.cursor + 1 : activeFile.line1
-    }`;
-  }, [activeFile.path, activeFile.cursor, activeFile.line1, activeFile.line2]);
-
-  const [attachFileCheckboxData, setAttachFile] = useState<Checkbox>({
-    name: "file_upload",
-    checked: !!activeFile.name && messageLength === 0 && hasSnippet,
-    label: "Attach",
-    value: filePathWithLines,
-    disabled: !activeFile.name,
-    fileName: activeFile.name,
-    hide: !shouldShow,
-    info: {
-      text: "Attaches the current file as context. If the file is large, it prefers the code near the current cursor position. Equivalent to @file name.ext:CURSOR_LINE in the text.",
-      link: "https://docs.refact.ai/features/ai-chat/",
-      linkText: "documentation",
+  const attached = useMemo(() => {
+    const maybeAttached = files.find((file) => file.path === activeFile.path);
+    return !!maybeAttached;
+  }, [activeFile.path, files]);
+
+  const addFile = useCallback(() => {
+    if (attached) return;
+    setFiles((prev) => {
+      return [...prev, activeFile];
+    });
+  }, [attached, activeFile]);
+
+  const removeFile = useCallback((fileToRemove: FileInfo) => {
+    setFiles((prev) => {
+      return prev.filter((file) => file.path !== fileToRemove.path);
+    });
+  }, []);
+
+  const addFilesToInput = useCallback(
+    (str: string) => {
+      if (files.length === 0) return str;
+      const result = files.reduce<string>((acc, file) => {
+        const hasLines = file.line1 !== null && file.line2 !== null;
+        if (!hasLines) return `@file ${file.path}\n${acc}`;
+        const line = file.cursor ? file.cursor + 1 : file.line1;
+        return `@file ${file.path}:${line}\n${acc}`;
+      }, str);
+      return result;
     },
-  });
+    [files],
+  );
 
-  useEffect(() => {
-    if (!interacted) {
-      setAttachFile((prev) => {
-        return {
-          ...prev,
-          hide: !shouldShow,
-          value: filePathWithLines,
-          disabled: !activeFile.name,
-          fileName: activeFile.name,
-          // checked: interacted ? prev.checked : !!activeFile.name && shouldShow,
-          checked: !!activeFile.name && shouldShow && hasSnippet,
-        };
-      });
-    }
-  }, [activeFile.name, filePathWithLines, hasSnippet, interacted, shouldShow]);
+  const removeAll = useCallback(() => {
+    setFiles([]);
+  }, []);
 
   useEffect(() => {
-    if (messageLength > 0 && attachFileCheckboxData.hide === false) {
-      setAttachFile((prev) => {
-        return { ...prev, hide: true, checked: false };
+    const handleIdeAttachFile = (filePath: string) => {
+      const fileInfo: FileInfo = {
+        name: filename(filePath),
+        path: filePath,
+        line1: null,
+        line2: null,
+        cursor: null,
+        can_paste: false,
+      };
+      setFiles((prev) => {
+        const maybeEntered = prev.find((file) => file.path === filePath);
+        if (maybeEntered) return prev;
+        return [...prev, fileInfo];
       });
-    }
-  }, [attachFileCheckboxData.hide, messageLength]);
+    };
 
-  const onToggleAttachFile = useCallback(() => {
-    setAttachFile((prev) => {
-      return {
-        ...prev,
-        checked: !prev.checked,
-      };
-    });
+    const listener = (event: MessageEvent) => {
+      if (ideAttachFileToChat.match(event.data)) {
+        handleIdeAttachFile(event.data.payload);
+      }
+    };
+
+    window.addEventListener("message", listener);
+    return () => {
+      window.removeEventListener("message", listener);
+    };
   }, []);
 
-  return [attachFileCheckboxData, onToggleAttachFile];
-};
+  return {
+    files,
+    activeFile,
+    addFile,
+    removeFile,
+    attached,
+    addFilesToInput,
+    removeAll,
+  };
+}
 
 const useAttachSelectedSnippet = (
   interacted: boolean,
@@ -167,66 +173,45 @@ const useAttachSelectedSnippet = (
 };
 
 export type Checkboxes = {
-  file_upload: Checkbox;
+  // file_upload: Checkbox;
   selected_lines: Checkbox;
 };
 
 export const useCheckboxes = () => {
-  // creating 2 different states instead of only one being used for both checkboxes
+  // creating different states instead of only one being used for checkboxes
   const [lineSelectionInteracted, setLineSelectionInteracted] = useState(false);
-  const [fileInteracted, setFileInteracted] = useState(false);
 
   const [attachedSelectedSnippet, onToggleAttachedSelectedSnippet] =
     useAttachSelectedSnippet(lineSelectionInteracted);
 
-  const [attachFileCheckboxData, onToggleAttachFile] = useAttachActiveFile(
-    fileInteracted,
-    attachedSelectedSnippet.checked,
-  );
-
   const checkboxes = useMemo(
     () => ({
-      file_upload: attachFileCheckboxData,
       selected_lines: attachedSelectedSnippet,
     }),
-    [attachFileCheckboxData, attachedSelectedSnippet],
+    [attachedSelectedSnippet],
   );
 
   const onToggleCheckbox = useCallback(
     (name: string) => {
       switch (name) {
-        case "file_upload":
-          onToggleAttachFile();
-          setFileInteracted(true);
-          break;
         case "selected_lines":
           onToggleAttachedSelectedSnippet();
-          setFileInteracted(true);
           setLineSelectionInteracted(true);
           break;
       }
     },
-    [onToggleAttachFile, onToggleAttachedSelectedSnippet],
+    [onToggleAttachedSelectedSnippet],
   );
 
   const unCheckAll = useCallback(() => {
-    if (attachFileCheckboxData.checked) {
-      onToggleAttachFile();
-    }
     if (attachedSelectedSnippet.checked) {
       onToggleAttachedSelectedSnippet();
     }
-  }, [
-    attachFileCheckboxData.checked,
-    attachedSelectedSnippet.checked,
-    onToggleAttachFile,
-    onToggleAttachedSelectedSnippet,
-  ]);
+  }, [attachedSelectedSnippet.checked, onToggleAttachedSelectedSnippet]);
 
   return {
     checkboxes,
     onToggleCheckbox,
-    setFileInteracted,
     setLineSelectionInteracted,
     unCheckAll,
   };
diff --git a/refact-agent/gui/src/components/ChatForm/useCommandCompletionAndPreviewFiles.ts b/refact-agent/gui/src/components/ChatForm/useCommandCompletionAndPreviewFiles.ts
index 9626cb4bb..80663f75a 100644
--- a/refact-agent/gui/src/components/ChatForm/useCommandCompletionAndPreviewFiles.ts
+++ b/refact-agent/gui/src/components/ChatForm/useCommandCompletionAndPreviewFiles.ts
@@ -110,8 +110,7 @@ function useGetCommandPreviewQuery(
 function useGetPreviewFiles(query: string, checkboxes: Checkboxes) {
   const queryWithCheckboxes = useMemo(
     () => addCheckboxValuesToInput(query, checkboxes),
-    // eslint-disable-next-line react-hooks/exhaustive-deps
-    [checkboxes, query, checkboxes.file_upload.value],
+    [checkboxes, query],
   );
   const [previewQuery, setPreviewQuery] = useState<string>(queryWithCheckboxes);
 
@@ -125,11 +124,7 @@ function useGetPreviewFiles(query: string, checkboxes: Checkboxes) {
 
   useEffect(() => {
     debounceSetPreviewQuery(queryWithCheckboxes);
-  }, [
-    debounceSetPreviewQuery,
-    queryWithCheckboxes,
-    checkboxes.file_upload.value,
-  ]);
+  }, [debounceSetPreviewQuery, queryWithCheckboxes]);
 
   const previewFileResponse = useGetCommandPreviewQuery(previewQuery);
   return previewFileResponse;
diff --git a/refact-agent/gui/src/components/ChatForm/utils.ts b/refact-agent/gui/src/components/ChatForm/utils.ts
index 38a684930..839d4ab0f 100644
--- a/refact-agent/gui/src/components/ChatForm/utils.ts
+++ b/refact-agent/gui/src/components/ChatForm/utils.ts
@@ -16,10 +16,6 @@ export function addCheckboxValuesToInput(
     result = `${checkboxes.selected_lines.value ?? ""}\n` + result;
   }
 
-  if (checkboxes.file_upload.checked && checkboxes.file_upload.hide !== true) {
-    result = `@file ${checkboxes.file_upload.value ?? ""}\n` + result;
-  }
-
   if (!result.endsWith("\n")) {
     result += "\n";
   }
@@ -27,6 +23,7 @@ export function addCheckboxValuesToInput(
   return result;
 }
 
+// TODO: delete this if unused
 export function activeFileToContextFile(fileInfo: FileInfo): ChatContextFile {
   const content = fileInfo.content ?? "";
   return {
diff --git a/refact-agent/gui/src/components/Dropzone/Dropzone.tsx b/refact-agent/gui/src/components/Dropzone/Dropzone.tsx
index 73168cc87..eeb28868f 100644
--- a/refact-agent/gui/src/components/Dropzone/Dropzone.tsx
+++ b/refact-agent/gui/src/components/Dropzone/Dropzone.tsx
@@ -6,6 +6,7 @@ import { useAttachedImages } from "../../hooks/useAttachedImages";
 import { TruncateLeft } from "../Text";
 import { telemetryApi } from "../../services/refact/telemetry";
 import { useCapsForToolUse } from "../../hooks";
+import { useAttachedFiles } from "../ChatForm/useCheckBoxes";
 
 export const FileUploadContext = createContext<{
   open: () => void;
@@ -77,7 +78,7 @@ export const DropzoneProvider: React.FC<
 
 export const DropzoneConsumer = FileUploadContext.Consumer;
 
-export const AttachFileButton = () => {
+export const AttachImagesButton = () => {
   const [sendTelemetryEvent] =
     telemetryApi.useLazySendTelemetryChatEventQuery();
   const attachFileOnClick = useCallback(
@@ -121,29 +122,52 @@ export const AttachFileButton = () => {
   );
 };
 
-export const FileList = () => {
+type FileListProps = {
+  attachedFiles: ReturnType<typeof useAttachedFiles>;
+};
+export const FileList: React.FC<FileListProps> = ({ attachedFiles }) => {
   const { images, removeImage } = useAttachedImages();
-  if (images.length === 0) return null;
+  if (images.length === 0 && attachedFiles.files.length === 0) return null;
   return (
     <Flex wrap="wrap" gap="1" py="2">
       {images.map((file, index) => {
         const key = `image-${file.name}-${index}`;
         return (
-          <Button
-            // variant="surface"
-            // variant="outline"
-            variant="soft"
-            radius="full"
+          <FileButton
             key={key}
-            size="1"
             onClick={() => removeImage(index)}
-            style={{ maxWidth: "100%" }}
-          >
-            <TruncateLeft wrap="wrap">{file.name}</TruncateLeft>{" "}
-            <Cross1Icon width="10" style={{ flexShrink: 0 }} />
-          </Button>
+            fileName={file.name}
+          />
+        );
+      })}
+      {attachedFiles.files.map((file, index) => {
+        const key = `file-${file.path}-${index}`;
+        return (
+          <FileButton
+            key={key}
+            fileName={file.name}
+            onClick={() => attachedFiles.removeFile(file)}
+          />
         );
       })}
     </Flex>
   );
 };
+
+const FileButton: React.FC<{ fileName: string; onClick: () => void }> = ({
+  fileName,
+  onClick,
+}) => {
+  return (
+    <Button
+      variant="soft"
+      radius="full"
+      size="1"
+      onClick={onClick}
+      style={{ maxWidth: "100%" }}
+    >
+      <TruncateLeft wrap="wrap">{fileName}</TruncateLeft>{" "}
+      <Cross1Icon width="10" style={{ flexShrink: 0 }} />
+    </Button>
+  );
+};
diff --git a/refact-agent/gui/src/components/Dropzone/index.tsx b/refact-agent/gui/src/components/Dropzone/index.tsx
index 164bf09b8..03debddab 100644
--- a/refact-agent/gui/src/components/Dropzone/index.tsx
+++ b/refact-agent/gui/src/components/Dropzone/index.tsx
@@ -2,6 +2,6 @@ export {
   DropzoneProvider,
   DropzoneConsumer,
   FileUploadContext,
-  AttachFileButton,
+  AttachImagesButton,
   FileList,
 } from "./Dropzone";
diff --git a/refact-agent/gui/src/events/index.ts b/refact-agent/gui/src/events/index.ts
index dc897daa9..b6f987208 100644
--- a/refact-agent/gui/src/events/index.ts
+++ b/refact-agent/gui/src/events/index.ts
@@ -78,6 +78,8 @@ export {
   ideToolCallResponse,
 } from "../hooks/useEventBusForIDE";
 
+export { ideAttachFileToChat } from "../hooks/useEventBusForApp";
+
 export const fim = {
   request,
   ready,
diff --git a/refact-agent/gui/src/hooks/index.ts b/refact-agent/gui/src/hooks/index.ts
index 6dfb21e34..28be44bc3 100644
--- a/refact-agent/gui/src/hooks/index.ts
+++ b/refact-agent/gui/src/hooks/index.ts
@@ -35,3 +35,4 @@ export * from "./useCompressChat";
 export * from "./useAutoFocusOnce";
 export * from "./useHideScroll";
 export * from "./useCompressionStop";
+export * from "./useEventBusForApp";
diff --git a/refact-agent/gui/src/hooks/useEventBusForApp.ts b/refact-agent/gui/src/hooks/useEventBusForApp.ts
index 51738a162..269201c55 100644
--- a/refact-agent/gui/src/hooks/useEventBusForApp.ts
+++ b/refact-agent/gui/src/hooks/useEventBusForApp.ts
@@ -13,6 +13,9 @@ import {
   selectPages,
 } from "../features/Pages/pagesSlice";
 import { ideToolCallResponse } from "./useEventBusForIDE";
+import { createAction } from "@reduxjs/toolkit/react";
+
+export const ideAttachFileToChat = createAction<string>("ide/attachFileToChat");
 
 export function useEventBusForApp() {
   const config = useConfig();