diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index 61419487cc..8ba0df7ab2 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -36,6 +36,26 @@ import { ZooCodeAuthBadge } from "./ZooCodeAuthBadge"
 import { usePromptHistory } from "./hooks/usePromptHistory"
 import { disabledChatControlClassName, enabledChatControlClassName } from "./chatControlStyles"
 
+// Data transfer types that signal a file-oriented drag rather than an in-webview
+// text selection drag. "Files" covers drags from the OS file manager; the
+// remaining types are set by VS Code when dragging resources from the Explorer
+// or editor tabs, in local and remote workspaces alike (see fillEditorsDragData
+// in VS Code's workbench drag-and-drop code). Bare text/uri-list also
+// identifies browser link drags, so it must retain native drop behavior.
+const FILE_DRAG_DATA_TRANSFER_TYPES = [
+	"Files",
+	"ResourceURLs",
+	"CodeEditors",
+	"CodeFiles",
+	"application/vnd.code.uri-list",
+]
+
+// Chromium lowercases custom drag types; compare without relying on casing.
+const isFileDrag = (dataTransfer: DataTransfer): boolean =>
+	dataTransfer.types.some((type) =>
+		FILE_DRAG_DATA_TRANSFER_TYPES.some((fileType) => fileType.toLowerCase() === type.toLowerCase()),
+	)
+
 interface ChatTextAreaProps {
 	inputValue: string
 	setInputValue: (value: string) => void
@@ -967,8 +987,11 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 						className={cn("chat-text-area", !isEditMode && "relative", "flex", "flex-col", "outline-none")}
 						onDrop={handleDrop}
 						onDragOver={(e) => {
-							// Only allowed to drop images/files on shift key pressed.
-							if (!e.shiftKey) {
+							// Accept file drags from the OS file manager, the VS Code
+							// Explorer, and editor tabs without requiring Shift. In-webview
+							// text drags, such as moving a selection inside the input, keep
+							// the browser's native drop behavior unless Shift is held.
+							if (!e.shiftKey && !isFileDrag(e.dataTransfer)) {
 								setIsDraggingOver(false)
 								return
 							}
diff --git a/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx b/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx
index 5cced6a92f..4668c39f71 100644
--- a/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx
+++ b/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx
@@ -521,6 +521,66 @@ describe("ChatTextArea", () => {
 			expect(setInputValue).not.toHaveBeenCalled()
 		})
 
+		describe("dragover acceptance", () => {
+			// jsdom has no DragEvent constructor, so build a plain cancelable
+			// Event and attach the drag payload the React handler expects.
+			const fireDragOver = (element: Element, types: string[], shiftKey = false) => {
+				const event = new Event("dragover", { bubbles: true, cancelable: true })
+				const dataTransfer = { types, files: [], dropEffect: "none" }
+				Object.defineProperty(event, "dataTransfer", { value: dataTransfer })
+				Object.defineProperty(event, "shiftKey", { value: shiftKey })
+				fireEvent(element, event)
+				return { event, dataTransfer }
+			}
+
+			it.each([
+				"Files",
+				"resourceurls",
+				"codeeditors",
+				"codefiles",
+				"application/vnd.code.uri-list",
+				"RESOURCEURLS",
+			])("accepts %s drags without Shift", (type) => {
+				const { container } = render(<ChatTextArea {...defaultProps} />)
+
+				const { event, dataTransfer } = fireDragOver(container.querySelector(".chat-text-area")!, [type])
+
+				expect(event.defaultPrevented).toBe(true)
+				expect(dataTransfer.dropEffect).toBe("copy")
+				expect(container.querySelector(".border-dashed")).not.toBeNull()
+			})
+
+			it.each([["text/plain"], ["text/uri-list"], ["text/plain", "text/uri-list"]])(
+				"keeps native behavior and clears the highlight for drag types %j without Shift",
+				(...types) => {
+					const { container } = render(<ChatTextArea {...defaultProps} />)
+					const target = container.querySelector(".chat-text-area")!
+					fireDragOver(target, ["Files"])
+					expect(container.querySelector(".border-dashed")).not.toBeNull()
+
+					const { event, dataTransfer } = fireDragOver(target, types)
+
+					expect(event.defaultPrevented).toBe(false)
+					expect(dataTransfer.dropEffect).toBe("none")
+					expect(container.querySelector(".border-dashed")).toBeNull()
+				},
+			)
+
+			it("still accepts plain text drags when Shift is held", () => {
+				const { container } = render(<ChatTextArea {...defaultProps} />)
+
+				const { event, dataTransfer } = fireDragOver(
+					container.querySelector(".chat-text-area")!,
+					["text/plain"],
+					true,
+				)
+
+				expect(event.defaultPrevented).toBe(true)
+				expect(dataTransfer.dropEffect).toBe("copy")
+				expect(container.querySelector(".border-dashed")).not.toBeNull()
+			})
+		})
+
 		describe("prompt history navigation", () => {
 			const mockClineMessages = [
 				{ type: "say", say: "user_feedback", text: "First prompt", ts: 1000 },