diff --git a/src/app/components/editor/utils.test.ts b/src/app/components/editor/utils.test.ts
new file mode 100644
index 0000000000..a45fedf7a0
--- /dev/null
+++ b/src/app/components/editor/utils.test.ts
@@ -0,0 +1,40 @@
+import { createEditor, Editor, Transforms } from 'slate';
+import { describe, expect, it } from 'vitest';
+import { getPrevWorldRange } from './utils';
+import { BlockType } from './types';
+
+const createTestEditor = (text: string) => {
+  const editor = createEditor();
+  editor.children = [{ type: BlockType.Paragraph, children: [{ text }] }];
+  return editor;
+};
+
+const selectAt = (editor: Editor, offset: number) => {
+  Transforms.select(editor, { path: [0, 0], offset });
+};
+
+describe('getPrevWorldRange', () => {
+  it('returns the word before the cursor', () => {
+    const editor = createTestEditor('hello :smile world');
+    selectAt(editor, 12);
+
+    const range = getPrevWorldRange(editor);
+    expect(range && Editor.string(editor, range)).toBe(':smile');
+  });
+
+  it('returns the whole word when the cursor sits inside it', () => {
+    const editor = createTestEditor('hello :smile world');
+    selectAt(editor, 9);
+
+    const range = getPrevWorldRange(editor);
+    expect(range && Editor.string(editor, range)).toBe(':smile');
+  });
+
+  it('returns the whole word when the cursor sits inside the last word', () => {
+    const editor = createTestEditor('hello :smile');
+    selectAt(editor, 9);
+
+    const range = getPrevWorldRange(editor);
+    expect(range && Editor.string(editor, range)).toBe(':smile');
+  });
+});
diff --git a/src/app/components/editor/utils.ts b/src/app/components/editor/utils.ts
index 1776f9fb08..bb34f5d7d8 100644
--- a/src/app/components/editor/utils.ts
+++ b/src/app/components/editor/utils.ts
@@ -181,11 +181,11 @@ const getPointUntilChar = (
   let prevPoint: BasePoint | undefined;
   let char: string | undefined;
 
+  const startPoint = Editor.point(editor, cursorPoint, { edge: 'start' });
   const pointItr = Editor.positions(editor, {
-    at: {
-      anchor: Editor.start(editor, []),
-      focus: Editor.point(editor, cursorPoint, { edge: 'start' }),
-    },
+    at: options.reverse
+      ? { anchor: Editor.start(editor, []), focus: startPoint }
+      : { anchor: startPoint, focus: Editor.end(editor, []) },
     unit: 'character',
     reverse: options.reverse,
   });
@@ -202,16 +202,21 @@ const getPointUntilChar = (
   return targetPoint;
 };
 
+// line breaks produce empty chars, not \n
+const isWorldBoundary = (char: string) => /\s|^$/.test(char);
+
 export const getPrevWorldRange = (editor: Editor): BaseRange | undefined => {
   const { selection } = editor;
   if (!selection || !Range.isCollapsed(selection)) return undefined;
   const [cursorPoint] = Range.edges(selection);
   const worldStartPoint = getPointUntilChar(editor, cursorPoint, {
     reverse: true,
-    // line breaks produce empty chars, not \n
-    match: (char) => /\s|^$/.test(char),
+    match: isWorldBoundary,
   });
-  return worldStartPoint && Editor.range(editor, worldStartPoint, cursorPoint);
+  if (!worldStartPoint) return undefined;
+  const worldEndPoint =
+    getPointUntilChar(editor, cursorPoint, { match: isWorldBoundary }) ?? cursorPoint;
+  return Editor.range(editor, worldStartPoint, worldEndPoint);
 };
 
 export const isEmptyEditor = (editor: Editor): boolean => {
diff --git a/src/app/features/room/RoomInput.test.tsx b/src/app/features/room/RoomInput.test.tsx
index 10186cc3b8..f61c9674c9 100644
--- a/src/app/features/room/RoomInput.test.tsx
+++ b/src/app/features/room/RoomInput.test.tsx
@@ -781,6 +781,51 @@ describe('RoomInput submit regressions', () => {
     );
   });
 
+  it('sends on touch pointerup when the tap never produces a click', async () => {
+    render(<RoomInputHarness />);
+    fireEvent.click(screen.getByRole('button', { name: 'Compose text' }));
+
+    fireEvent.pointerDown(sendButton(), { pointerType: 'touch' });
+    fireEvent.pointerUp(sendButton(), { pointerType: 'touch' });
+
+    await waitFor(() => expect(testState.matrix.sendMessage).toHaveBeenCalledOnce());
+  });
+
+  it('sends once when a touch tap produces both a pointerup and a click', async () => {
+    render(<RoomInputHarness />);
+    fireEvent.click(screen.getByRole('button', { name: 'Compose text' }));
+
+    const submit = sendButton();
+    fireEvent.pointerDown(submit, { pointerType: 'touch' });
+    fireEvent.pointerUp(submit, { pointerType: 'touch' });
+    fireEvent.click(submit);
+
+    await waitFor(() => expect(testState.matrix.sendMessage).toHaveBeenCalledOnce());
+  });
+
+  it('cancels a touch send released outside the button', () => {
+    render(<RoomInputHarness />);
+    fireEvent.click(screen.getByRole('button', { name: 'Compose text' }));
+
+    fireEvent.pointerDown(sendButton(), { pointerType: 'touch' });
+    fireEvent.pointerUp(sendButton(), { pointerType: 'touch', clientX: 200, clientY: 200 });
+
+    expect(testState.matrix.sendMessage).not.toHaveBeenCalled();
+  });
+
+  it('leaves mouse taps on the click path', async () => {
+    render(<RoomInputHarness />);
+    fireEvent.click(screen.getByRole('button', { name: 'Compose text' }));
+
+    const submit = sendButton();
+    fireEvent.pointerDown(submit, { pointerType: 'mouse' });
+    fireEvent.pointerUp(submit, { pointerType: 'mouse' });
+    expect(testState.matrix.sendMessage).not.toHaveBeenCalled();
+
+    fireEvent.click(submit);
+    await waitFor(() => expect(testState.matrix.sendMessage).toHaveBeenCalledOnce());
+  });
+
   it('waits for an attachment transaction instead of sending text independently', async () => {
     const upload = deferred<{ content_uri: string }>();
     const file = new File(['attachment'], 'attachment.txt', { type: 'text/plain' });
diff --git a/src/app/features/room/RoomInput.tsx b/src/app/features/room/RoomInput.tsx
index d3436d030d..7367b9d425 100644
--- a/src/app/features/room/RoomInput.tsx
+++ b/src/app/features/room/RoomInput.tsx
@@ -1,4 +1,10 @@
-import type { KeyboardEventHandler, MouseEvent, ReactElement, RefObject } from 'react';
+import type {
+  KeyboardEventHandler,
+  MouseEvent,
+  PointerEvent,
+  ReactElement,
+  RefObject,
+} from 'react';
 import {
   forwardRef,
   Fragment,
@@ -408,6 +414,7 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
     const uploadBoardHandlers = useRef<UploadBoardImperativeHandlers>();
     const longPressTimer = useRef<ReturnType<typeof setTimeout> | null>(null);
     const isLongPress = useRef(false);
+    const sentOnPointerUpRef = useRef(false);
     const suppressBlurRefocusRef = useRef(false);
     const editorRafIdsRef = useRef(new Set<number>());
     const scheduleEditorRaf = useCallback((callback: () => void) => {
@@ -2518,6 +2525,7 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
                       isLongPress.current = false;
                       return;
                     }
+                    if (sentOnPointerUpRef.current) return;
                     submit();
                     return;
                   }
@@ -2530,6 +2538,7 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
                   if (hasContent) e.preventDefault();
                 }}
                 onPointerDown={() => {
+                  sentOnPointerUpRef.current = false;
                   if (showAudioRecorder) return;
                   if (hasContent) {
                     isLongPress.current = false;
@@ -2577,11 +2586,26 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
                   window.addEventListener('pointerup', onUp);
                   window.addEventListener('pointercancel', discardRecording);
                 }}
-                onPointerUp={() => {
+                onPointerUp={(evt: PointerEvent<HTMLButtonElement>) => {
                   if (longPressTimer.current !== null) {
                     clearTimeout(longPressTimer.current);
                     longPressTimer.current = null;
                   }
+                  // iOS drops the synthesized click when the page mutates during a tap.
+                  if (evt.pointerType === 'mouse') return;
+                  if (showAudioRecorder || !hasContent || isLongPress.current) return;
+                  // Touch implicitly captures the pointer, so a release off the button lands here too.
+                  const rect = evt.currentTarget.getBoundingClientRect();
+                  if (
+                    evt.clientX < rect.left ||
+                    evt.clientX > rect.right ||
+                    evt.clientY < rect.top ||
+                    evt.clientY > rect.bottom
+                  ) {
+                    return;
+                  }
+                  sentOnPointerUpRef.current = true;
+                  submit();
                 }}
                 onPointerCancel={() => {
                   if (longPressTimer.current !== null) {
diff --git a/src/client/initMatrix.ts b/src/client/initMatrix.ts
index 7e910c4034..05734821ea 100644
--- a/src/client/initMatrix.ts
+++ b/src/client/initMatrix.ts
@@ -13,6 +13,7 @@ import {
   SyncState,
 } from '$types/matrix-sdk';
 import { fetch } from '$utils/fetch';
+import { matrixFetch } from './matrixFetch';
 import { clearMediaCache } from '$utils/mediaCache';
 
 import { clearNavToActivePathStore } from '$state/navToActivePath';
@@ -250,7 +251,7 @@ const buildClient = async (session: Session): Promise<BuiltClient> => {
 
   const mx = createClient({
     baseUrl: session.baseUrl,
-    fetchFn: fetch,
+    fetchFn: matrixFetch,
     accessToken: session.accessToken,
     refreshToken: session.refreshToken,
     userId: session.userId,
diff --git a/src/client/matrixFetch.test.ts b/src/client/matrixFetch.test.ts
new file mode 100644
index 0000000000..1354e81bff
--- /dev/null
+++ b/src/client/matrixFetch.test.ts
@@ -0,0 +1,44 @@
+import { describe, expect, it, vi } from 'vitest';
+import { createMatrixFetch } from './matrixFetch';
+
+describe('createMatrixFetch', () => {
+  it('adds a timeout abort only to Matrix event send PUTs', async () => {
+    const baseFetch = vi.fn<typeof fetch>(() => Promise.resolve(new Response()));
+    const matrixFetch = createMatrixFetch(baseFetch);
+
+    await matrixFetch('https://matrix.example/_matrix/client/v3/sync');
+    await matrixFetch(
+      'https://matrix.example/_matrix/client/v3/rooms/!r:ex/send/m.room.message/m1',
+      { method: 'PUT' }
+    );
+    await matrixFetch(
+      'https://matrix.example/_matrix/client/v3/rooms/!r:ex/send/m.room.encrypted/m2',
+      { method: 'PUT' }
+    );
+    await matrixFetch('https://matrix.example/_matrix/client/v3/rooms/!r:ex/redact/$e/m3', {
+      method: 'PUT',
+    });
+
+    expect(baseFetch.mock.calls[0]?.[1]?.signal).toBeUndefined();
+    expect(baseFetch.mock.calls[1]?.[1]?.signal).toBeInstanceOf(AbortSignal);
+    expect(baseFetch.mock.calls[2]?.[1]?.signal).toBeInstanceOf(AbortSignal);
+    expect(baseFetch.mock.calls[3]?.[1]?.signal).toBeUndefined();
+  });
+
+  it('merges with an existing abort signal on the request', async () => {
+    const baseFetch = vi.fn<typeof fetch>(() => Promise.resolve(new Response()));
+    const matrixFetch = createMatrixFetch(baseFetch);
+    const controller = new AbortController();
+
+    await matrixFetch(
+      new Request('https://matrix.example/_matrix/client/v3/rooms/!r:ex/send/m.room.message/m1', {
+        method: 'PUT',
+        signal: controller.signal,
+      })
+    );
+
+    const signal = baseFetch.mock.calls[0]?.[1]?.signal;
+    expect(signal).toBeInstanceOf(AbortSignal);
+    expect(signal).not.toBe(controller.signal);
+  });
+});
diff --git a/src/client/matrixFetch.ts b/src/client/matrixFetch.ts
new file mode 100644
index 0000000000..cb903b9670
--- /dev/null
+++ b/src/client/matrixFetch.ts
@@ -0,0 +1,55 @@
+import { fetch } from '$utils/fetch';
+
+/** Timeline event sends use `PUT /_matrix/client/{ver}/rooms/{roomId}/send/{type}/{txnId}`. */
+const MATRIX_EVENT_SEND_PATH = /\/_matrix\/client\/[^/]+\/rooms\/[^/]+\/send\//;
+
+const EVENT_SEND_TIMEOUT_MS = 30_000;
+
+const requestUrl = (input: RequestInfo | URL): string =>
+  typeof input === 'string' ? input : input instanceof URL ? input.href : input.url;
+
+const requestMethod = (input: RequestInfo | URL, init?: RequestInit): string => {
+  if (init?.method) return init.method.toUpperCase();
+  if (input instanceof Request) return input.method.toUpperCase();
+  return 'GET';
+};
+
+const isMatrixEventSend = (input: RequestInfo | URL, init?: RequestInit): boolean => {
+  const method = requestMethod(input, init);
+  if (method !== 'PUT') return false;
+  return MATRIX_EVENT_SEND_PATH.test(new URL(requestUrl(input)).pathname);
+};
+
+const mergeAbortSignals = (signals: AbortSignal[]): AbortSignal => {
+  const controller = new AbortController();
+  for (const signal of signals) {
+    if (signal.aborted) {
+      controller.abort(signal.reason);
+      return controller.signal;
+    }
+    signal.addEventListener('abort', () => controller.abort(signal.reason), { once: true });
+  }
+  return controller.signal;
+};
+
+/**
+ * Wraps the app fetch so stalled timeline sends abort after 30s. That makes the
+ * SDK mark the local echo `NOT_SENT`, which unlocks retry without a global client timeout.
+ */
+export const createMatrixFetch = (baseFetch: typeof fetch = fetch): typeof fetch => {
+  const matrixFetch: typeof fetch = (input, init) => {
+    if (!isMatrixEventSend(input, init)) {
+      return baseFetch(input, init);
+    }
+
+    const timeout = AbortSignal.timeout(EVENT_SEND_TIMEOUT_MS);
+    const existingSignal = init?.signal ?? (input instanceof Request ? input.signal : undefined);
+    const signal = existingSignal ? mergeAbortSignals([existingSignal, timeout]) : timeout;
+
+    return baseFetch(input, { ...init, signal });
+  };
+
+  return matrixFetch;
+};
+
+export const matrixFetch = createMatrixFetch();