diff --git a/pyproject.toml b/pyproject.toml
index df1202451..f731bc3f2 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,7 +1,7 @@
 [project]
 name = "goose-ai"
 description = "a programming agent that runs on your machine"
-version = "0.8.4"
+version = "0.8.5"
 readme = "README.md"
 requires-python = ">=3.10"
 dependencies = [
diff --git a/src/goose/cli/session.py b/src/goose/cli/session.py
index 3da620d33..713bd1f8c 100644
--- a/src/goose/cli/session.py
+++ b/src/goose/cli/session.py
@@ -2,7 +2,7 @@
 from pathlib import Path
 from typing import Any, Dict, List, Optional
 
-from exchange import Message, ToolResult, ToolUse
+from exchange import Message, ToolResult, ToolUse, Text
 from prompt_toolkit.shortcuts import confirm
 from rich import print
 from rich.console import RenderableType
@@ -24,6 +24,8 @@
 from goose.utils import droid, load_plugins
 from goose.utils.session_file import read_from_file, write_to_file
 
+RESUME_MESSAGE = "I see we were interrupted. How can I help you?"
+
 
 def load_provider() -> str:
     # We try to infer a provider, by going in order of what will auth
@@ -91,8 +93,22 @@ def __init__(
 
         if name is not None and self.session_file_path.exists():
             messages = self.load_session()
+
             if messages and messages[-1].role == "user":
+                if type(messages[-1].content[-1]) is Text:
+                    # remove the last user message
+                    messages.pop()
+                elif type(messages[-1].content[-1]) is ToolResult:
+                    # if we remove this message, we would need to remove
+                    # the previous assistant message as well. instead of doing
+                    # that, we just add a new assistant message to prompt the user
+                    messages.append(Message.assistant(RESUME_MESSAGE))
+            if messages and type(messages[-1].content[-1]) is ToolUse:
+                # remove the last request for a tool to be used
                 messages.pop()
+
+                # add a new assistant text message to prompt the user
+                messages.append(Message.assistant(RESUME_MESSAGE))
             self.exchange.messages.extend(messages)
 
         if len(self.exchange.messages) == 0 and plan:
diff --git a/tests/cli/test_session.py b/tests/cli/test_session.py
index 83dd6ebaf..79a7c4a2b 100644
--- a/tests/cli/test_session.py
+++ b/tests/cli/test_session.py
@@ -1,7 +1,7 @@
 from unittest.mock import MagicMock, patch
 
 import pytest
-from exchange import Message
+from exchange import Message, ToolUse, ToolResult
 from goose.cli.prompt.goose_prompt_session import GoosePromptSession
 from goose.cli.prompt.user_input import PromptAction, UserInput
 from goose.cli.session import Session
@@ -32,7 +32,7 @@ def create_session(session_attributes: dict = {}):
         yield create_session
 
 
-def test_session_does_not_extend_last_user_message_on_init(
+def test_session_does_not_extend_last_user_text_message_on_init(
     create_session_with_mock_configs, mock_sessions_path, create_session_file
 ):
     messages = [Message.user("Hello"), Message.assistant("Hi"), Message.user("Last should be removed")]
@@ -44,6 +44,41 @@ def test_session_does_not_extend_last_user_message_on_init(
     assert [message.text for message in session.exchange.messages] == ["Hello", "Hi"]
 
 
+def test_session_adds_resume_message_if_last_message_is_tool_result(
+    create_session_with_mock_configs, mock_sessions_path, create_session_file
+):
+    messages = [
+        Message.user("Hello"),
+        Message(role="assistant", content=[ToolUse(id="1", name="first_tool", parameters={})]),
+        Message(role="user", content=[ToolResult(tool_use_id="1", output="output")]),
+    ]
+    create_session_file(messages, mock_sessions_path / f"{SESSION_NAME}.jsonl")
+
+    session = create_session_with_mock_configs({"name": SESSION_NAME})
+    print("Messages after session init:", session.exchange.messages)  # Debugging line
+    assert len(session.exchange.messages) == 4
+    assert session.exchange.messages[-1].role == "assistant"
+    assert session.exchange.messages[-1].text == "I see we were interrupted. How can I help you?"
+
+
+def test_session_removes_tool_use_and_adds_resume_message_if_last_message_is_tool_use(
+    create_session_with_mock_configs, mock_sessions_path, create_session_file
+):
+    messages = [
+        Message.user("Hello"),
+        Message(role="assistant", content=[ToolUse(id="1", name="first_tool", parameters={})]),
+    ]
+    create_session_file(messages, mock_sessions_path / f"{SESSION_NAME}.jsonl")
+
+    session = create_session_with_mock_configs({"name": SESSION_NAME})
+    print("Messages after session init:", session.exchange.messages)  # Debugging line
+    assert len(session.exchange.messages) == 2
+    assert [message.text for message in session.exchange.messages] == [
+        "Hello",
+        "I see we were interrupted. How can I help you?",
+    ]
+
+
 def test_save_session_create_session(mock_sessions_path, create_session_with_mock_configs, mock_specified_session_name):
     session = create_session_with_mock_configs()
     session.exchange.messages.append(Message.assistant("Hello"))