diff --git a/crates/core/src/closet_llm.rs b/crates/core/src/closet_llm.rs
index dde80ee..a5b31ac 100644
--- a/crates/core/src/closet_llm.rs
+++ b/crates/core/src/closet_llm.rs
@@ -158,10 +158,18 @@ pub fn regenerate_closets(
 }
 
 fn regenerate_entry(content: &str, endpoint: &str) -> Result<String, RegenerateError> {
+    regenerate_entry_with_delay(content, endpoint, INITIAL_DELAY_MS)
+}
+
+fn regenerate_entry_with_delay(
+    content: &str,
+    endpoint: &str,
+    initial_delay_ms: u64,
+) -> Result<String, RegenerateError> {
     let prompt = REGENERATE_PROMPT.replace("{context}", content);
 
     let client = reqwest::blocking::Client::new();
-    let mut delay_ms = INITIAL_DELAY_MS;
+    let mut delay_ms = initial_delay_ms;
 
     for attempt in 0..MAX_RETRIES {
         let response = client
@@ -178,11 +186,38 @@ fn regenerate_entry(content: &str, endpoint: &str) -> Result<String, RegenerateE
             Ok(resp) => {
                 let status = resp.status();
                 if status.is_success() {
-                    let parsed: LlmResponse = resp.json().map_err(RegenerateError::Http)?;
-                    if parsed.response.trim().is_empty() {
-                        return Err(RegenerateError::Empty);
+                    // Read the body as text first so we can retry malformed
+                    // JSON (truncated streams / partial chunks under load on
+                    // local LLM runtimes). Mirrors upstream mempalace 2a0ed0c
+                    // (#1155) which moved JSONDecodeError onto the same
+                    // exponential-backoff path as 429/503.
+                    let body = match resp.text() {
+                        Ok(b) => b,
+                        Err(e) => {
+                            if attempt < MAX_RETRIES - 1 {
+                                std::thread::sleep(std::time::Duration::from_millis(delay_ms));
+                                delay_ms *= 2;
+                                continue;
+                            }
+                            return Err(RegenerateError::Http(e));
+                        }
+                    };
+                    match serde_json::from_str::<LlmResponse>(&body) {
+                        Ok(parsed) => {
+                            if parsed.response.trim().is_empty() {
+                                return Err(RegenerateError::Empty);
+                            }
+                            return Ok(parsed.response.trim().to_string());
+                        }
+                        Err(e) => {
+                            if attempt < MAX_RETRIES - 1 {
+                                std::thread::sleep(std::time::Duration::from_millis(delay_ms));
+                                delay_ms *= 2;
+                                continue;
+                            }
+                            return Err(RegenerateError::InvalidJson(e));
+                        }
                     }
-                    return Ok(parsed.response.trim().to_string());
                 }
 
                 if status.as_u16() == 429 || status.as_u16() == 503 && attempt < MAX_RETRIES - 1 {
@@ -231,4 +266,79 @@ mod tests {
         let debug = format!("{:?}", stats);
         assert!(debug.contains("2"));
     }
+
+    /// Minimal mock HTTP/1.1 server used by the retry tests below.
+    ///
+    /// `responses` is consumed in order: each connection gets the next body.
+    /// The first byte of every body is treated as a 200-OK payload (since
+    /// upstream's bug only fires on the success branch).
+    fn spawn_mock_server(responses: Vec<String>) -> (String, std::thread::JoinHandle<()>) {
+        use std::io::{Read, Write};
+        use std::net::TcpListener;
+
+        let listener = TcpListener::bind("127.0.0.1:0").expect("bind ephemeral port");
+        let addr = listener.local_addr().unwrap();
+        let url = format!("http://{}/", addr);
+
+        let handle = std::thread::spawn(move || {
+            for body in responses {
+                let (mut stream, _) = match listener.accept() {
+                    Ok(pair) => pair,
+                    Err(_) => return,
+                };
+                // Read the request (and discard it).
+                let mut buf = [0u8; 4096];
+                let _ = stream.read(&mut buf);
+                let response = format!(
+                    "HTTP/1.1 200 OK\r\nContent-Type: application/json\r\n\
+                     Content-Length: {}\r\nConnection: close\r\n\r\n{}",
+                    body.len(),
+                    body
+                );
+                let _ = stream.write_all(response.as_bytes());
+                let _ = stream.flush();
+            }
+        });
+
+        (url, handle)
+    }
+
+    #[test]
+    fn test_regenerate_entry_retries_on_invalid_json() {
+        // Regression for upstream mempalace 2a0ed0c (#1155): the first
+        // attempt returning malformed JSON must be retried, not bailed.
+        // Two malformed bodies, then a valid one — must succeed on attempt 3.
+        let (url, handle) = spawn_mock_server(vec![
+            "not-json{".to_string(),
+            "{\"response\":".to_string(),
+            "{\"response\": \"OK\"}".to_string(),
+        ]);
+
+        // Use a small initial delay so the test does not wait the
+        // production 1s+2s+... backoff schedule.
+        let result = regenerate_entry_with_delay("hello", &url, 1);
+        assert!(
+            result.is_ok(),
+            "expected retry to succeed, got {:?}",
+            result
+        );
+        assert_eq!(result.unwrap(), "OK");
+
+        let _ = handle.join();
+    }
+
+    #[test]
+    fn test_regenerate_entry_returns_invalid_json_after_all_retries_fail() {
+        // If every attempt returns malformed JSON, the final error must be
+        // surfaced as InvalidJson (not Empty / not Http).
+        let (url, handle) = spawn_mock_server(vec!["not-json".to_string(); MAX_RETRIES as usize]);
+
+        let result = regenerate_entry_with_delay("hello", &url, 1);
+        match result {
+            Err(RegenerateError::InvalidJson(_)) => {}
+            other => panic!("expected InvalidJson, got {:?}", other),
+        }
+
+        let _ = handle.join();
+    }
 }
diff --git a/crates/core/src/diary_ingest.rs b/crates/core/src/diary_ingest.rs
index d763ab4..a168b80 100644
--- a/crates/core/src/diary_ingest.rs
+++ b/crates/core/src/diary_ingest.rs
@@ -74,15 +74,27 @@ pub fn ingest_diaries(
             })
             .unwrap_or("unknown");
 
-        // Skip if content hasn't changed
+        // Skip if content hasn't changed. Hash-based — size alone false-negatives
+        // on same-length edits (e.g. "teh" → "the"), silently dropping real edits.
         let state_key = format!(
             "{}|{}",
             wing,
             diary_path.file_name().unwrap_or_default().to_string_lossy()
         );
         let curr_size = text.len();
-        if state.get(&state_key).map(|s| s.size) == Some(curr_size) && !force {
-            continue;
+        let curr_hash = format!("{:x}", Sha256::digest(text.as_bytes()));
+        if !force {
+            if let Some(prev) = state.get(&state_key) {
+                if let Some(prev_hash) = prev.content_hash.as_ref() {
+                    if prev_hash == &curr_hash {
+                        continue;
+                    }
+                } else if prev.size > 0 && prev.size == curr_size {
+                    // Legacy state without content_hash: keep size-based skip so a
+                    // post-upgrade run doesn't re-ingest every untouched diary.
+                    continue;
+                }
+            }
         }
 
         let now_iso = chrono_now_iso();
@@ -121,6 +133,7 @@ pub fn ingest_diaries(
             state_key,
             StateEntry {
                 size: curr_size,
+                content_hash: Some(curr_hash),
                 entry_count: entries.len(),
                 ingested_at: now_iso,
             },
@@ -148,6 +161,11 @@ pub fn ingest_diaries(
 #[derive(Debug, Clone, serde::Serialize, serde::Deserialize)]
 struct StateEntry {
     size: usize,
+    /// sha256 hex digest of the diary file's text content. `None` is the
+    /// legacy schema (size-only); kept optional so a post-upgrade run does
+    /// not re-ingest every untouched diary.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    content_hash: Option<String>,
     entry_count: usize,
     ingested_at: String,
 }
@@ -294,4 +312,86 @@ mod tests {
         let id = diary_drawer_id("diary", "2024-01-15");
         assert!(id.starts_with("drawer_diary_"));
     }
+
+    #[test]
+    fn test_state_entry_legacy_format_deserializes_without_content_hash() {
+        // Regression for upstream mempalace 0d1c1fb: legacy state files
+        // written before the content_hash field existed must still load.
+        let legacy = r#"{"size": 42, "entry_count": 3, "ingested_at": "2024-01-01T00:00:00"}"#;
+        let parsed: StateEntry = serde_json::from_str(legacy).unwrap();
+        assert_eq!(parsed.size, 42);
+        assert_eq!(parsed.entry_count, 3);
+        assert!(parsed.content_hash.is_none());
+    }
+
+    #[test]
+    fn test_state_entry_round_trips_with_content_hash() {
+        let entry = StateEntry {
+            size: 10,
+            content_hash: Some("deadbeef".to_string()),
+            entry_count: 1,
+            ingested_at: "2024-01-01T00:00:00".to_string(),
+        };
+        let json = serde_json::to_string(&entry).unwrap();
+        assert!(json.contains("content_hash"));
+        let parsed: StateEntry = serde_json::from_str(&json).unwrap();
+        assert_eq!(parsed.content_hash.as_deref(), Some("deadbeef"));
+    }
+
+    #[test]
+    fn test_ingest_diaries_detects_same_size_edit() {
+        // Regression for upstream mempalace 0d1c1fb (#925): an in-place edit
+        // that preserves byte length (e.g. "teh" -> "the") was silently
+        // dropped under the old size-only gate. Switch to content_hash.
+        let _guard = crate::test_env_lock()
+            .lock()
+            .expect("test env lock should be available");
+        let temp = tempfile::TempDir::new().unwrap();
+        let prev_home = std::env::var_os("HOME");
+        // diary_ingest::state_file_for uses $HOME/.mempalace/state — point it
+        // at the tempdir so the test does not pollute real home.
+        std::env::set_var("HOME", temp.path());
+
+        let palace_path = temp.path().join("palace");
+        let diary_dir = temp.path().join("diaries");
+        std::fs::create_dir_all(&diary_dir).unwrap();
+
+        // Write a diary file with enough content to clear the >50-byte filter.
+        let diary_file = diary_dir.join("2024-01-15.md");
+        let original = "## Notes\n\nteh quick brown fox jumps over the lazy dog and again here.\n";
+        std::fs::write(&diary_file, original).unwrap();
+
+        let stats = ingest_diaries(&diary_dir, Some(&palace_path), "diary", false).unwrap();
+        assert_eq!(
+            stats.days_updated, 1,
+            "first ingest should record the diary"
+        );
+
+        // Second ingest with no change: must skip.
+        let stats = ingest_diaries(&diary_dir, Some(&palace_path), "diary", false).unwrap();
+        assert_eq!(
+            stats.days_updated, 0,
+            "second ingest with unchanged content should skip"
+        );
+
+        // Same-size edit: "teh" -> "the". Old gate would silently drop this.
+        let edited = original.replace("teh", "the");
+        assert_eq!(
+            edited.len(),
+            original.len(),
+            "test fixture must preserve length"
+        );
+        std::fs::write(&diary_file, &edited).unwrap();
+
+        let stats = ingest_diaries(&diary_dir, Some(&palace_path), "diary", false).unwrap();
+        assert_eq!(
+            stats.days_updated, 1,
+            "same-size edit must be detected via content hash"
+        );
+
+        match prev_home {
+            Some(h) => std::env::set_var("HOME", h),
+            None => std::env::remove_var("HOME"),
+        }
+    }
 }
diff --git a/crates/core/src/exporter.rs b/crates/core/src/exporter.rs
index 8c410ba..57b777b 100644
--- a/crates/core/src/exporter.rs
+++ b/crates/core/src/exporter.rs
@@ -18,6 +18,26 @@ fn safe_path_component(name: &str) -> String {
     }
 }
 
+/// Refuse to write into a path that is itself a symlink.
+///
+/// Defense-in-depth: a pre-placed symlink at the export target would
+/// redirect writes to wherever it points (e.g., system directories).
+/// Mirrors the miner's input-side caution.
+fn reject_symlink(path: &Path, label: &str) -> anyhow::Result<()> {
+    if std::fs::symlink_metadata(path)
+        .map(|m| m.file_type().is_symlink())
+        .unwrap_or(false)
+    {
+        anyhow::bail!(
+            "refusing to export: {} is a symbolic link ({}). \
+             Remove the symlink or choose a different output path.",
+            label,
+            path.display()
+        );
+    }
+    Ok(())
+}
+
 pub struct ExportStats {
     pub wings: usize,
     pub rooms: usize,
@@ -39,6 +59,7 @@ pub fn export_palace(palace_path: Option<&Path>, output_dir: &Path) -> anyhow::R
         });
     }
 
+    reject_symlink(output_dir, "output_dir")?;
     std::fs::create_dir_all(output_dir)?;
     #[cfg(unix)]
     {
@@ -82,8 +103,10 @@ pub fn export_palace(palace_path: Option<&Path>, output_dir: &Path) -> anyhow::R
                 .and_then(|v| v.as_str())
                 .unwrap_or("general");
 
-            let wing_dir = output_dir.join(safe_path_component(wing));
+            let safe_wing = safe_path_component(wing);
+            let wing_dir = output_dir.join(&safe_wing);
             if !created_wing_dirs.contains_key(wing) {
+                reject_symlink(&wing_dir, &format!("wing directory '{}'", safe_wing))?;
                 std::fs::create_dir_all(&wing_dir)?;
                 created_wing_dirs.insert(wing.to_string(), true);
             }
@@ -213,3 +236,39 @@ fn chrono_now_date() -> String {
     let day = remaining + 1;
     format!("{:04}-{:02}-{:02}", y, month, day)
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_reject_symlink_allows_regular_path() {
+        let temp = tempfile::TempDir::new().unwrap();
+        let regular = temp.path().join("regular");
+        std::fs::create_dir_all(&regular).unwrap();
+        assert!(reject_symlink(&regular, "output_dir").is_ok());
+    }
+
+    #[test]
+    fn test_reject_symlink_allows_missing_path() {
+        let temp = tempfile::TempDir::new().unwrap();
+        let missing = temp.path().join("missing");
+        // A path that does not exist is fine — `create_dir_all` will create it.
+        assert!(reject_symlink(&missing, "output_dir").is_ok());
+    }
+
+    #[cfg(unix)]
+    #[test]
+    fn test_reject_symlink_blocks_symlinked_dir() {
+        let temp = tempfile::TempDir::new().unwrap();
+        let target = temp.path().join("real");
+        std::fs::create_dir_all(&target).unwrap();
+        let link = temp.path().join("link");
+        std::os::unix::fs::symlink(&target, &link).unwrap();
+
+        let err = reject_symlink(&link, "output_dir").unwrap_err();
+        let msg = format!("{}", err);
+        assert!(msg.contains("symbolic link"), "unexpected error: {msg}");
+        assert!(msg.contains("output_dir"), "unexpected error: {msg}");
+    }
+}
diff --git a/crates/core/src/miner.rs b/crates/core/src/miner.rs
index 0cf162c..321e23d 100644
--- a/crates/core/src/miner.rs
+++ b/crates/core/src/miner.rs
@@ -265,6 +265,31 @@ impl GitignoreMatcher {
     }
 }
 
+/// Split `value` into lowercased tokens bounded by `-`, `_`, `.` or `/`.
+fn tokens(value: &str) -> HashSet<String> {
+    value
+        .to_lowercase()
+        .split(['-', '_', '.', '/'])
+        .filter(|t| !t.is_empty())
+        .map(|t| t.to_string())
+        .collect()
+}
+
+/// Return true when `a` and `b` match as equal strings or as
+/// separator-bounded tokens of each other.
+///
+/// Prevents incidental substring collisions (e.g., `"views" in "interviews"`)
+/// that a raw `contains` check would produce, while preserving the intended
+/// match for real tokens (e.g., `"frontend"` in `"frontend-app"`).
+fn name_matches(a: &str, b: &str) -> bool {
+    let a_lower = a.to_lowercase();
+    let b_lower = b.to_lowercase();
+    if a_lower == b_lower {
+        return true;
+    }
+    tokens(&a_lower).contains(&b_lower) || tokens(&b_lower).contains(&a_lower)
+}
+
 fn glob_matches(pattern: &str, candidate: &str) -> bool {
     let mut regex = String::from("^");
     for ch in pattern.chars() {
@@ -541,9 +566,10 @@ impl Miner {
             for room in &self.rooms {
                 let mut candidates = vec![room.name.to_lowercase()];
                 candidates.extend(room.keywords.iter().map(|keyword| keyword.to_lowercase()));
-                if candidates.iter().any(|candidate| {
-                    part == *candidate || candidate.contains(&part) || part.contains(candidate)
-                }) {
+                if candidates
+                    .iter()
+                    .any(|candidate| name_matches(&part, candidate))
+                {
                     return room.name.clone();
                 }
             }
@@ -551,7 +577,7 @@ impl Miner {
 
         for room in &self.rooms {
             let room_name_lower = room.name.to_lowercase();
-            if room_name_lower.contains(&filename) || filename.contains(&room_name_lower) {
+            if name_matches(&filename, &room_name_lower) {
                 return room.name.clone();
             }
         }
@@ -966,6 +992,56 @@ mod tests {
         assert_eq!(room, "backend");
     }
 
+    #[test]
+    fn test_name_matches_token_boundary() {
+        // exact match
+        assert!(name_matches("backend", "backend"));
+        // case-insensitive equality
+        assert!(name_matches("Backend", "BACKEND"));
+        // separator-bounded token match
+        assert!(name_matches("frontend-app", "frontend"));
+        assert!(name_matches("auth_service", "auth"));
+        assert!(name_matches("api.v1", "api"));
+        // negative: substring without token boundary must NOT match
+        assert!(!name_matches("interviews", "views"));
+        assert!(!name_matches("background", "back"));
+        assert!(!name_matches("authenticate", "auth"));
+    }
+
+    #[test]
+    fn test_detect_room_does_not_misroute_substring() {
+        // Regression for upstream mempalace ead2c5d: "views" ⊂ "interviews"
+        // must not route every interviews/* file to a "views" room.
+        let rooms = vec![RoomMapping {
+            name: "views".to_string(),
+            description: "View templates".to_string(),
+            keywords: vec![],
+        }];
+        let miner = Miner::new(std::path::Path::new("/tmp"), "test", rooms).unwrap();
+
+        let room = miner.detect_room(
+            std::path::Path::new("/tmp/project/interviews/q1.py"),
+            "interview question",
+        );
+        assert_eq!(room, "general");
+    }
+
+    #[test]
+    fn test_detect_room_matches_separator_bounded_token() {
+        let rooms = vec![RoomMapping {
+            name: "frontend".to_string(),
+            description: "Frontend code".to_string(),
+            keywords: vec![],
+        }];
+        let miner = Miner::new(std::path::Path::new("/tmp"), "test", rooms).unwrap();
+
+        let room = miner.detect_room(
+            std::path::Path::new("/tmp/project/frontend-app/index.tsx"),
+            "import React",
+        );
+        assert_eq!(room, "frontend");
+    }
+
     #[test]
     fn test_scan_project_respects_gitignore() {
         let temp = tempfile::TempDir::new().unwrap();