diff --git a/roboco/api/routes/messages.py b/roboco/api/routes/messages.py
index 073b8ff7..9414ba5e 100644
--- a/roboco/api/routes/messages.py
+++ b/roboco/api/routes/messages.py
@@ -25,6 +25,7 @@ from roboco.services.messaging import (
     MessageCreateRequest as ServiceMessageRequest,
 )
 from roboco.services.messaging import (
+    MessageCursor,
     get_messaging_service,
 )
 
@@ -45,10 +46,20 @@ async def list_messages(
     """List messages in a session (session existence is checked in the service)."""
     messaging = get_messaging_service(db)
     try:
+        before_cursor = (
+            MessageCursor(params.before, params.before_id)
+            if params.before is not None
+            else None
+        )
+        after_cursor = (
+            MessageCursor(params.after, params.after_id)
+            if params.after is not None
+            else None
+        )
         messages, has_more = await messaging.list_messages_for_session(
             session_id=params.session_id,
-            before=params.before,
-            after=params.after,
+            before=before_cursor,
+            after=after_cursor,
             message_type=params.type_filter,
             limit=params.limit,
         )
diff --git a/roboco/api/schemas/messages.py b/roboco/api/schemas/messages.py
index 18b8aeeb..f45f9f09 100644
--- a/roboco/api/schemas/messages.py
+++ b/roboco/api/schemas/messages.py
@@ -23,6 +23,12 @@ class ListMessagesParams(BaseModel):
     session_id: UUID
     before: datetime | None = None
     after: datetime | None = None
+    # Keyset-pagination tie-breakers: pass the last (before) / first (after)
+    # message's id alongside its timestamp so equal-timestamp messages are not
+    # skipped across pages. Optional — a timestamp-only cursor keeps the
+    # legacy strict-inequality behavior.
+    before_id: UUID | None = None
+    after_id: UUID | None = None
     type_filter: MessageType | None = None
     limit: int = Field(50, ge=1, le=100)
 
diff --git a/roboco/services/messaging.py b/roboco/services/messaging.py
index 07158193..647ec813 100644
--- a/roboco/services/messaging.py
+++ b/roboco/services/messaging.py
@@ -16,7 +16,7 @@ from datetime import UTC, datetime, timedelta
 from typing import Any, ClassVar, cast
 from uuid import UUID
 
-from sqlalchemy import select
+from sqlalchemy import and_, or_, select
 from sqlalchemy.exc import IntegrityError
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.orm import joinedload, selectinload
@@ -76,6 +76,23 @@ def _minutes_to_timedelta(value: int | None) -> timedelta | None:
 # =============================================================================
 
 
+@dataclass(frozen=True, slots=True)
+class MessageCursor:
+    """A keyset-pagination cursor over messages: a ``(timestamp, id)`` pair.
+
+    The ``id`` tie-breaks equal timestamps so paging across same-timestamp
+    messages skips nothing: the next page resumes past the cursor's id at
+    the shared timestamp rather than being excluded by a strict
+    ``timestamp < cursor`` / ``timestamp > cursor`` inequality (which drops
+    every row sharing the cursor's timestamp — they are cut by ``limit`` on
+    the prior page and never returned). ``id`` is ``None`` for a legacy
+    timestamp-only cursor (strict inequality, the prior behavior).
+    """
+
+    timestamp: datetime
+    id: UUID | None = None
+
+
 class MessagingService(BaseService):
     """
     Service for managing all messaging operations.
@@ -1571,8 +1588,8 @@ class MessagingService(BaseService):
         self,
         *,
         session_id: UUID,
-        before: datetime | None,
-        after: datetime | None,
+        before: MessageCursor | None,
+        after: MessageCursor | None,
         message_type: MessageType | None,
         limit: int,
     ) -> tuple[list[MessageTable], bool]:
@@ -1580,7 +1597,10 @@ class MessagingService(BaseService):
 
         Existing `get_messages` skips the session-existence check — this
         variant raises NotFoundError when the session is missing so routes
-        can return a clean 404 without issuing their own query.
+        can return a clean 404 without issuing their own query. The ``before``
+        / ``after`` cursors carry the keyset ``(timestamp, id)`` pair so
+        callers can paginate without skipping equal-timestamp messages across
+        pages.
         """
         await self.get_session_or_raise(session_id)
         return await self.get_messages(
@@ -1668,8 +1688,8 @@ class MessagingService(BaseService):
     async def get_messages(
         self,
         session_id: UUID,
-        before: datetime | None = None,
-        after: datetime | None = None,
+        before: MessageCursor | None = None,
+        after: MessageCursor | None = None,
         message_type: MessageType | None = None,
         limit: int = 50,
     ) -> tuple[list[MessageTable], bool]:
@@ -1678,8 +1698,12 @@ class MessagingService(BaseService):
 
         Args:
             session_id: Session to get messages from
-            before: Get messages before this timestamp
-            after: Get messages after this timestamp
+            before: Keyset cursor — return messages older than (or, when the
+                cursor carries an id, equal-timestamp-but-smaller-id than) this
+                position. ``None`` for no upper bound.
+            after: Keyset cursor — return messages newer than (or
+                equal-timestamp-but-larger-id than) this position. ``None`` for
+                no lower bound.
             message_type: Filter by message type
             limit: Maximum messages to return
 
@@ -1688,15 +1712,48 @@ class MessagingService(BaseService):
         """
         query = select(MessageTable).where(MessageTable.session_id == session_id)
 
-        if before:
-            query = query.where(MessageTable.timestamp < before)
-        if after:
-            query = query.where(MessageTable.timestamp > after)
+        if before is not None:
+            if before.id is not None:
+                # Compound keyset cursor: resume past (before.timestamp,
+                # before.id) in desc order. Rows where (timestamp, id) <
+                # (before.timestamp, before.id): strictly older, OR same
+                # timestamp with a smaller id. Without this tie-break,
+                # equal-timestamp rows cut by ``limit`` on the prior page are
+                # excluded by the strict ``< before.timestamp`` and vanish.
+                query = query.where(
+                    or_(
+                        MessageTable.timestamp < before.timestamp,
+                        and_(
+                            MessageTable.timestamp == before.timestamp,
+                            MessageTable.id < before.id,
+                        ),
+                    )
+                )
+            else:
+                query = query.where(MessageTable.timestamp < before.timestamp)
+        if after is not None:
+            if after.id is not None:
+                query = query.where(
+                    or_(
+                        MessageTable.timestamp > after.timestamp,
+                        and_(
+                            MessageTable.timestamp == after.timestamp,
+                            MessageTable.id > after.id,
+                        ),
+                    )
+                )
+            else:
+                query = query.where(MessageTable.timestamp > after.timestamp)
         if message_type:
             query = query.where(MessageTable.type == message_type)
 
-        # Get one extra to check if there are more
-        query = query.order_by(MessageTable.timestamp.desc()).limit(limit + 1)
+        # Deterministic total order: timestamp desc, then id desc so the
+        # "last item" cursor is unambiguous for keyset pagination (without the
+        # id tie-break, same-timestamp rows have a non-deterministic order and
+        # the cursor is ambiguous).
+        query = query.order_by(
+            MessageTable.timestamp.desc(), MessageTable.id.desc()
+        ).limit(limit + 1)
 
         result = await self.session.execute(query)
         messages = list(result.scalars().all())
diff --git a/tests/integration/test_messaging_service.py b/tests/integration/test_messaging_service.py
index 6f20dc68..00c09fe9 100644
--- a/tests/integration/test_messaging_service.py
+++ b/tests/integration/test_messaging_service.py
@@ -7,7 +7,7 @@ from datetime import UTC, datetime, timedelta
 from types import SimpleNamespace
 from typing import TYPE_CHECKING, Any, cast
 from unittest.mock import AsyncMock, patch
-from uuid import uuid4
+from uuid import UUID, uuid4
 from uuid import uuid4 as _u
 
 import pytest
@@ -38,6 +38,7 @@ from roboco.models.session import (
 from roboco.services.base import ConflictError, NotFoundError
 from roboco.services.messaging import (
     ApiSessionCreate,
+    MessageCursor,
     MessagingService,
     get_messaging_service,
 )
@@ -1106,8 +1107,8 @@ async def test_get_messages_with_filters(msg_setup: dict) -> None:
     cutoff = datetime.now(UTC) - timedelta(hours=1)
     msgs, _ = await svc.get_messages(
         sess.id,
-        before=datetime.now(UTC) + timedelta(hours=1),
-        after=cutoff,
+        before=MessageCursor(datetime.now(UTC) + timedelta(hours=1)),
+        after=MessageCursor(cutoff),
         message_type=MessageType.DIALOGUE,
     )
     assert isinstance(msgs, list)
@@ -1130,6 +1131,113 @@ async def test_get_messages_with_limit(msg_setup: dict) -> None:
     assert has_more is True
 
 
+async def _seed_messages_same_timestamp(
+    svc: MessagingService, session: Any, aid: UUID, count: int
+) -> tuple[UUID, list[UUID]]:
+    """Create ``count`` messages in one session and force them ALL to the same
+    timestamp so the equal-timestamp pagination skip is reproducible. Returns
+    ``(session_id, message_ids)``."""
+    ch = await svc.create_channel(_channel_req(uuid4().hex[:6]))
+    grp = await svc.create_group(GroupCreateRequest(name="g1", channel_id=ch.id))
+    sess = await svc.create_session(SessionCreateRequest(group_id=grp.id))
+    ids: list[UUID] = []
+    for i in range(count):
+        m = await svc.send_message(
+            MessageCreateRequest(agent_id=aid, session_id=sess.id, content=f"m-{i}")
+        )
+        ids.append(m.id)
+    fixed = datetime.now(UTC)
+    rows = (
+        (
+            await session.execute(
+                select(MessageTable).where(MessageTable.session_id == sess.id)
+            )
+        )
+        .scalars()
+        .all()
+    )
+    for row in rows:
+        row.timestamp = fixed
+    await session.flush()
+    return sess.id, ids
+
+
+@pytest.mark.asyncio
+async def test_get_messages_compound_before_cursor_no_skip_on_equal_timestamps(
+    msg_setup: dict,
+) -> None:
+    """Equal-timestamp messages must not be skipped across pages (F106).
+
+    With a strict ``timestamp < before`` cursor and ``order_by(timestamp.desc())``,
+    messages sharing the page's last timestamp are cut by ``limit`` on page 1
+    and excluded (``< T``) from page 2 — they vanish. The compound
+    ``(timestamp, id)`` cursor tie-breaks on the unique id so the next page
+    resumes exactly past the last id (no skip, no duplicate). Requires the
+    deterministic ``order_by(timestamp.desc(), id.desc())`` so the "last item"
+    cursor is unambiguous.
+    """
+    svc = msg_setup["svc"]
+    session = svc.session
+    aid = msg_setup["agent_id"]
+    total = 5
+    sess_id, ids = await _seed_messages_same_timestamp(svc, session, aid, count=total)
+
+    page_size = 3
+    page1, has_more = await svc.get_messages(sess_id, limit=page_size)
+    assert has_more is True
+    assert len(page1) == page_size
+    # Deterministic order: same timestamp → by id.desc()
+    page1_ids = [m.id for m in page1]
+    assert page1_ids == sorted(page1_ids, reverse=True)
+
+    last = page1[-1]
+    page2, has_more2 = await svc.get_messages(
+        sess_id, before=MessageCursor(last.timestamp, last.id), limit=page_size
+    )
+    # All 5 covered, no skip, no duplicate.
+    seen = {m.id for m in page1} | {m.id for m in page2}
+    assert seen == set(ids)
+    assert len(page1) + len(page2) == total
+    assert has_more2 is False
+
+
+@pytest.mark.asyncio
+async def test_get_messages_compound_after_cursor_no_skip_on_equal_timestamps(
+    msg_setup: dict,
+) -> None:
+    """Forward pagination (``after``) with the compound ``(timestamp, id)``
+    cursor tie-breaks on id so newer-direction pagination across equal
+    timestamps skips nothing either (F106).
+
+    With a strict ``timestamp > after`` cursor, every row sharing the cursor's
+    timestamp is EXCLUDED — so forward-paginating from a middle message would
+    return nothing (all rows are at the same timestamp, none strictly greater).
+    The compound cursor includes same-timestamp rows with a larger id.
+    """
+    svc = msg_setup["svc"]
+    session = svc.session
+    aid = msg_setup["agent_id"]
+    total = 5
+    fetch_limit = 10
+    mid_index = 2
+    newer_count = 2
+    sess_id, _ids = await _seed_messages_same_timestamp(svc, session, aid, count=total)
+
+    # Full desc ordering: [id_largest, ..., id_smallest].
+    all_msgs, _ = await svc.get_messages(sess_id, limit=fetch_limit)
+    assert len(all_msgs) == total
+    # Pick the middle row as the forward cursor.
+    mid = all_msgs[mid_index]
+    newer = {m.id for m in all_msgs[:newer_count]}  # the rows above mid (larger id)
+
+    page, _ = await svc.get_messages(
+        sess_id, after=MessageCursor(mid.timestamp, mid.id), limit=fetch_limit
+    )
+    # The same-timestamp rows newer than mid are returned — NOT skipped.
+    assert {m.id for m in page} == newer
+    assert len(page) == newer_count
+
+
 @pytest.mark.asyncio
 async def test_get_message_context_redirects_when_session_closed(
     msg_setup: dict,