diff --git a/src-tauri/src/assistant/compaction.rs b/src-tauri/src/assistant/compaction.rs
index 81183b2..a309266 100644
--- a/src-tauri/src/assistant/compaction.rs
+++ b/src-tauri/src/assistant/compaction.rs
@@ -402,17 +402,47 @@ Preserve:
 
 Do not include filler, greetings, or obsolete intermediate details. Do not invent facts. Write a compact but complete continuation summary."#;
 
+/// Preamble prepended to every stored compaction summary message.
+const SUMMARY_MESSAGE_PREAMBLE: &str =
+    "Conversation summary generated by CLAI compaction. Treat this as the \
+     authoritative summary of the compacted earlier messages. If you are \
+     missing context needed to continue, recover it before acting rather \
+     than asking the user to repeat anything: your durable state is in \
+     `.clai/memory/` and the full verbatim history (every message and tool \
+     result) is in `.clai/data.sqlite` — query it with the read-only \
+     `history_query` tool (no approval needed) to recover specifics.";
+
+/// Preamble that opens a deterministic (non-model) digest body.
+const FALLBACK_DIGEST_PREAMBLE: &str =
+    "Deterministic compaction summary: the previous conversation was \
+     compacted without a model-generated summary. Below is a noise-reduced \
+     transcript digest — tool payloads are truncated, and when the history \
+     is too long the opening exchanges (the original goal) and the most \
+     recent exchanges are kept while the middle is dropped. Continue from \
+     it, and recover anything that was elided from `.clai/memory/` or by \
+     querying the full history with the read-only `history_query` tool \
+     (it reads `.clai/data.sqlite` and needs no approval).";
+
 fn summary_message_text(summary: &str) -> String {
-    format!(
-        "Conversation summary generated by CLAI compaction. Treat this as the \
-         authoritative summary of the compacted earlier messages. If you are \
-         missing context needed to continue, recover it before acting rather \
-         than asking the user to repeat anything: your durable state is in \
-         `.clai/memory/` and the full verbatim history (every message and tool \
-         result) is in `.clai/data.sqlite` — query it with the read-only \
-         `history_query` tool (no approval needed) to recover specifics.\n\n{}",
-        summary.trim()
-    )
+    format!("{}\n\n{}", SUMMARY_MESSAGE_PREAMBLE, summary.trim())
+}
+
+/// A chained compaction feeds the previous summary message back through the
+/// renderer. Its preambles are pure boilerplate that the *new* summary message
+/// re-adds anyway, so carrying them forward stacks one more copy per rotation
+/// while telling the model nothing it isn't already told at the top.
+fn strip_compaction_preambles(text: &str) -> String {
+    let mut out = text.trim_start();
+    loop {
+        let next = out
+            .strip_prefix(SUMMARY_MESSAGE_PREAMBLE)
+            .or_else(|| out.strip_prefix(FALLBACK_DIGEST_PREAMBLE));
+        match next {
+            Some(rest) => out = rest.trim_start(),
+            None => break,
+        }
+    }
+    out.to_string()
 }
 
 fn transcript_for_summary(messages: &[AssistantMessage]) -> String {
@@ -438,17 +468,7 @@ fn fallback_summary(messages: &[AssistantMessage]) -> String {
         DIGEST_TOOL_RESULT_MAX_CHARS,
     );
     let body = select_head_and_tail(&rendered, SUMMARY_TRANSCRIPT_MAX_CHARS);
-    format!(
-        "Deterministic compaction summary: the previous conversation was \
-         compacted without a model-generated summary. Below is a noise-reduced \
-         transcript digest — tool payloads are truncated, and when the history \
-         is too long the opening exchanges (the original goal) and the most \
-         recent exchanges are kept while the middle is dropped. Continue from \
-         it, and recover anything that was elided from `.clai/memory/` or by \
-         querying the full history with the read-only `history_query` tool \
-         (it reads `.clai/data.sqlite` and needs no approval).\n\n{}",
-        body
-    )
+    format!("{}\n\n{}", FALLBACK_DIGEST_PREAMBLE, body)
 }
 
 /// Join rendered messages within `budget`, always at whole-message boundaries.
@@ -493,9 +513,16 @@ fn select_head_and_tail(rendered: &[String], budget: usize) -> String {
         tail_start -= 1;
     }
 
+    let head = clamp_slice(&rendered[..head_end], head_budget, Keep::Start);
+    let tail = clamp_slice(&rendered[tail_start..], tail_budget, Keep::End);
+
     // Head and tail meet (everything fits across the two slices): no omission.
     if tail_start <= head_end {
-        return rendered.join("\n\n");
+        return [head, tail]
+            .into_iter()
+            .filter(|part| !part.is_empty())
+            .collect::<Vec<_>>()
+            .join("\n\n");
     }
 
     let omitted = tail_start - head_end;
@@ -504,13 +531,48 @@ fn select_head_and_tail(rendered: &[String], budget: usize) -> String {
         "{}\n\n[... {} middle message{} omitted during compaction; recover the \
          full verbatim history with the read-only `history_query` tool \
          (`.clai/data.sqlite`) ...]\n\n{}",
-        rendered[..head_end].join("\n\n"),
-        omitted,
-        suffix,
-        rendered[tail_start..].join("\n\n")
+        head, omitted, suffix, tail
     )
 }
 
+const MESSAGE_TRUNCATION_NOTE: &str =
+    "\n\n[... this message was truncated during compaction; recover its full \
+     text with the read-only `history_query` tool (`.clai/data.sqlite`) ...]\n\n";
+
+/// Join a selected slice, capping any single message at the slice budget.
+///
+/// The "keep at least one message" rules above accept one oversized message per
+/// slice, which is how a chained compaction used to grow without bound: message
+/// 0 of a rotation window is the *previous* digest, so an uncapped head copied
+/// the whole predecessor into every successor. Truncate rather than drop — the
+/// opening message still has to survive, just not at any size.
+fn clamp_slice(messages: &[String], budget: usize, keep: Keep) -> String {
+    messages
+        .iter()
+        .map(|message| clamp_message(message, budget, keep))
+        .collect::<Vec<_>>()
+        .join("\n\n")
+}
+
+/// Which end of an oversized message to keep: the head slice exists to preserve
+/// the opening goal, the tail slice to preserve the most recent exchange.
+#[derive(Clone, Copy)]
+enum Keep {
+    Start,
+    End,
+}
+
+fn clamp_message(message: &str, budget: usize, keep: Keep) -> String {
+    if message.len() <= budget {
+        return message.to_string();
+    }
+    let room = budget.saturating_sub(MESSAGE_TRUNCATION_NOTE.len());
+    match keep {
+        Keep::Start => format!("{}{}", safe_prefix(message, room), MESSAGE_TRUNCATION_NOTE),
+        Keep::End => format!("{}{}", MESSAGE_TRUNCATION_NOTE, safe_suffix(message, room)),
+    }
+}
+
 fn render_transcript(messages: &[AssistantMessage]) -> String {
     render_messages(
         messages,
@@ -537,12 +599,13 @@ fn render_messages(
                 MessageRole::Assistant => "assistant",
                 MessageRole::Tool => "tool",
             };
-            format!(
-                "[{} message {}]\n{}",
-                role,
-                message.id,
-                render_content_parts(&message.content, tool_call_max, tool_result_max)
-            )
+            let body = render_content_parts(&message.content, tool_call_max, tool_result_max);
+            let body = if is_compaction_summary_message(message) {
+                strip_compaction_preambles(&body)
+            } else {
+                body
+            };
+            format!("[{} message {}]\n{}", role, message.id, body)
         })
         .collect()
 }
@@ -746,6 +809,122 @@ mod tests {
         assert!(out.contains("history_query"));
     }
 
+    fn summary_msg(id: &str, body: &str) -> AssistantMessage {
+        AssistantMessage {
+            provider_metadata: Some(serde_json::json!({ "source": COMPACTION_METADATA_SOURCE })),
+            ..msg(
+                id,
+                MessageRole::System,
+                vec![text(&summary_message_text(body))],
+            )
+        }
+    }
+
+    #[test]
+    fn select_head_and_tail_never_exceeds_budget_on_one_huge_message() {
+        // Message 0 of a rotation window is the previous digest: it can be far
+        // larger than the whole budget on its own. It must be truncated, not
+        // copied through, or every digest inherits its predecessor's size.
+        let budget = 4_000;
+        let rendered = vec![
+            "H".repeat(500_000),
+            "middle".to_string(),
+            "T".repeat(500_000),
+        ];
+        let out = select_head_and_tail(&rendered, budget);
+        assert!(
+            out.len() <= budget + 400,
+            "digest blew the budget: {} chars for a {budget}-char budget",
+            out.len()
+        );
+        assert!(out.starts_with('H'), "head dropped entirely");
+        assert!(out.trim_end().ends_with('T'), "tail dropped entirely");
+        assert!(out.contains("truncated during compaction"), "{out}");
+    }
+
+    #[test]
+    fn select_head_and_tail_bounds_output_when_head_and_tail_meet() {
+        // Two messages, both oversized: head and tail meet, so the omission
+        // branch never runs — the clamp still has to hold.
+        let budget = 2_000;
+        let rendered = vec!["H".repeat(80_000), "T".repeat(80_000)];
+        let out = select_head_and_tail(&rendered, budget);
+        assert!(
+            out.len() <= budget + 400,
+            "digest blew the budget: {} chars",
+            out.len()
+        );
+    }
+
+    #[test]
+    fn chained_digests_do_not_grow_without_bound() {
+        // Simulate repeated session rotations: each digest becomes message 0 of
+        // the next window. Before the fix this grew by roughly the size of the
+        // previous digest every round (measured: 56 KB -> 960 KB over 20
+        // rotations against a 96 KB budget).
+        let mut carried = fallback_summary(&[msg(
+            "seed",
+            MessageRole::User,
+            vec![text(&"the original goal ".repeat(2_000))],
+        )]);
+        let mut sizes = Vec::new();
+        for round in 0..12 {
+            let mut window = vec![summary_msg(&format!("digest-{round}"), &carried)];
+            for i in 0..30 {
+                window.push(msg(
+                    &format!("m-{round}-{i}"),
+                    MessageRole::Assistant,
+                    vec![text(&format!("turn {i} of round {round} ").repeat(200))],
+                ));
+            }
+            carried = fallback_summary(&window);
+            sizes.push(carried.len());
+        }
+        let last = *sizes.last().unwrap();
+        assert!(
+            last <= SUMMARY_TRANSCRIPT_MAX_CHARS + 2_000,
+            "digest exceeded its budget after chaining: {last} chars, sizes {sizes:?}"
+        );
+        // And it is not creeping upward round over round.
+        assert!(
+            last <= sizes[1] + 2_000,
+            "digest grew across rotations: {sizes:?}"
+        );
+    }
+
+    #[test]
+    fn chained_digests_do_not_stack_preambles() {
+        // One boilerplate preamble per digest, no matter how many rotations.
+        let mut carried = fallback_summary(&[msg("seed", MessageRole::User, vec![text("goal")])]);
+        for round in 0..6 {
+            let window = vec![
+                summary_msg(&format!("digest-{round}"), &carried),
+                msg("u", MessageRole::User, vec![text("next")]),
+            ];
+            carried = fallback_summary(&window);
+        }
+        let stored = summary_message_text(&carried);
+        assert_eq!(
+            stored
+                .matches("Conversation summary generated by CLAI")
+                .count(),
+            1,
+            "summary preamble stacked: {stored}"
+        );
+        assert_eq!(
+            stored.matches("Deterministic compaction summary").count(),
+            1,
+            "digest preamble stacked: {stored}"
+        );
+    }
+
+    #[test]
+    fn strip_compaction_preambles_leaves_ordinary_text_alone() {
+        assert_eq!(strip_compaction_preambles("plain body"), "plain body");
+        let wrapped = summary_message_text("real content here");
+        assert_eq!(strip_compaction_preambles(&wrapped), "real content here");
+    }
+
     #[test]
     fn summary_message_text_includes_recovery_guidance() {
         let out = summary_message_text("the summary body");