diff --git a/letta/prompts/summarizer_prompt.py b/letta/prompts/summarizer_prompt.py
index f6ddc48a..cb9d12d4 100644
--- a/letta/prompts/summarizer_prompt.py
+++ b/letta/prompts/summarizer_prompt.py
@@ -30,21 +30,19 @@ Write the summary from the perspective of the AI (use the first person from the
 Only output the summary, do NOT include anything else in your output.
 """
 
-WORD_LIMIT = 100
-SHORTER_SUMMARY_PROMPT = f"""You have been interacting with a human user, and are in the middle of a conversation or a task. Write a summary that will allow you (or another instance of yourself) to resume without distruption, even after the conversation history is replaced with this summary. Your summary should be structured, concise, and actionable (if you are in the middle of a task). Include:
+WORD_LIMIT = 250
+SHORTER_SUMMARY_PROMPT = f"""The following messages are being evicted from your context window. Write a detailed summary that captures what happened in these messages.
 
-1. Task or conversational overview
-The user's core request and success criteria you are currently working on.
-Any clarifications or constraints they specified.
-Any details about the topic of messages that originated the current conversation or task.
+This summary will appear BEFORE the remaining recent messages in context, providing background for what comes after. Include:
 
-2. Current State
-What has been completed or discussed so far
-Files created, modified, or analyzed (with paths if relevant)
-Resources explored or referenced (with URLs if relevant)
-What has been discussed or explored so far with the user
+1. **What happened**: The conversations, tasks, and exchanges that took place. What did the user ask for? What did you do? How did things progress?
 
-3. Next Steps
-The next actions or steps you would have taken, if you were to continue the conversation or task.
+2. **Key outcomes**: Decisions made, tasks completed, files created (with paths), information gathered, problems solved, and any commitments made.
 
-Keep your summary less than {WORD_LIMIT} words, do NOT exceed this word limit. Only output the summary, do NOT include anything else in your output."""
+3. **Important details**: Specific names, data, configurations, or facts that were discussed. Don't omit details that might be referenced later.
+
+4. **Lookup hints**: For any detailed content (long lists, extensive data, specific conversations) that couldn't fit in the summary, note the topic and key terms that could be used to find it in message history later.
+
+Write in first person as a factual record of what occurred. Be thorough and detailed - the goal is to preserve enough context that the recent messages make sense and important information isn't lost.
+
+Keep your summary under {WORD_LIMIT} words. Only output the summary."""
diff --git a/letta/services/summarizer/summarizer_sliding_window.py b/letta/services/summarizer/summarizer_sliding_window.py
index d38ca58e..c5f91a99 100644
--- a/letta/services/summarizer/summarizer_sliding_window.py
+++ b/letta/services/summarizer/summarizer_sliding_window.py
@@ -127,7 +127,9 @@ async def summarize_via_sliding_window(
         # need to keep the last message (might contain an approval request)
         raise ValueError(f"Assistant message index {assistant_message_index} is at the end of the message buffer, skipping summarization")
 
-    messages_to_summarize = in_context_messages[1:assistant_message_index]
+    # Include the assistant message at the cutoff point so conversations are complete
+    # (otherwise the slice ends with a user question and the LLM answers it instead of summarizing)
+    messages_to_summarize = in_context_messages[1 : assistant_message_index + 1]
     logger.info(
         f"Summarizing {len(messages_to_summarize)} messages, from index 1 to {assistant_message_index} (out of {total_message_count})"
     )
@@ -144,5 +146,6 @@ async def summarize_via_sliding_window(
         logger.warning(f"Summary length {len(summary_message_str)} exceeds clip length {summarizer_config.clip_chars}. Truncating.")
         summary_message_str = summary_message_str[: summarizer_config.clip_chars] + "... [summary truncated to fit]"
 
-    updated_in_context_messages = in_context_messages[assistant_message_index:]
+    # Start remaining messages AFTER the assistant message we included in the summary
+    updated_in_context_messages = in_context_messages[assistant_message_index + 1 :]
     return summary_message_str, [system_prompt] + updated_in_context_messages