2 files changed, 206 insertions, 32 deletions

diff --git a/src/nostr/builder.rs b/src/nostr/builder.rs
index 34014db..629c111 100644
--- a/src/nostr/builder.rs
+++ b/src/nostr/builder.rs
@@ -98,6 +98,62 @@ impl Nip34WritePolicy {
         self.ctx.set_local_relay(relay);
     }
 
+    /// Extract repository identifier from event's 'd' tag.
+    ///
+    /// Used for structured logging when parsing fails - we try to extract
+    /// the identifier even if full parsing failed.
+    fn extract_identifier_from_event(event: &Event) -> String {
+        use nostr_relay_builder::prelude::TagKind;
+        event
+            .tags
+            .iter()
+            .find(|t| t.kind() == TagKind::d())
+            .and_then(|t| t.content())
+            .map(|s| s.to_string())
+            .unwrap_or_else(|| "unknown".to_string())
+    }
+
+    /// Extract ALL repository identifiers from PR event's 'a' tags.
+    ///
+    /// PR events can reference multiple repositories via multiple 'a' tags
+    /// (e.g., when there are multiple maintainers). Each tag has format
+    /// `30617:<owner_pubkey>:<identifier>`.
+    ///
+    /// Returns a vector of unique identifiers, or `["unknown"]` if none found.
+    fn extract_repos_from_pr_event(event: &Event) -> Vec<String> {
+        let repos: Vec<String> = event
+            .tags
+            .iter()
+            .filter_map(|tag| {
+                let tag_vec = tag.clone().to_vec();
+                if tag_vec.len() >= 2 && tag_vec[0] == "a" && tag_vec[1].starts_with("30617:") {
+                    // Format: 30617:<owner_pubkey>:<identifier>
+                    let parts: Vec<&str> = tag_vec[1].split(':').collect();
+                    if parts.len() >= 3 {
+                        Some(parts[2].to_string())
+                    } else {
+                        None
+                    }
+                } else {
+                    None
+                }
+            })
+            .collect();
+
+        // Deduplicate while preserving order
+        let mut seen = std::collections::HashSet::new();
+        let unique_repos: Vec<String> = repos
+            .into_iter()
+            .filter(|r| seen.insert(r.clone()))
+            .collect();
+
+        if unique_repos.is_empty() {
+            vec!["unknown".to_string()]
+        } else {
+            unique_repos
+        }
+    }
+
     /// Handle repository announcement event
     async fn handle_announcement(&self, event: &Event) -> WritePolicyResult {
         let event_id_str = event.id.to_bech32().unwrap_or_else(|_| event.id.to_hex());
@@ -129,10 +185,18 @@ impl Nip34WritePolicy {
                         WritePolicyResult::Accept
                     }
                     Err(e) => {
+                        let npub = event.pubkey.to_bech32().unwrap_or_else(|_| event.pubkey.to_hex());
+                        let event_id_short = &event.id.to_hex()[..12];
+                        // Try to extract repo identifier from 'd' tag even if parsing failed
+                        let repo = Self::extract_identifier_from_event(event);
+                        // Structured log for migration scripts
                         tracing::warn!(
-                            "Failed to parse repository announcement {}: {}",
-                            event_id_str,
-                            e
+                            "[PARSE_FAIL] kind={} event_id={}... reason=\"{}\" repo={} npub={}",
+                            event.kind.as_u16(),
+                            event_id_short,
+                            e,
+                            repo,
+                            npub
                         );
                         WritePolicyResult::reject(format!("Failed to parse announcement: {}", e))
                     }
@@ -157,10 +221,18 @@ impl Nip34WritePolicy {
                         WritePolicyResult::Accept
                     }
                     Err(e) => {
+                        let npub = event.pubkey.to_bech32().unwrap_or_else(|_| event.pubkey.to_hex());
+                        let event_id_short = &event.id.to_hex()[..12];
+                        // Try to extract repo identifier from 'd' tag even if parsing failed
+                        let repo = Self::extract_identifier_from_event(event);
+                        // Structured log for migration scripts
                         tracing::warn!(
-                            "Failed to parse maintainer announcement {}: {}",
-                            event_id_str,
-                            e
+                            "[PARSE_FAIL] kind={} event_id={}... reason=\"{}\" repo={} npub={}",
+                            event.kind.as_u16(),
+                            event_id_short,
+                            e,
+                            repo,
+                            npub
                         );
                         WritePolicyResult::reject(format!("Failed to parse announcement: {}", e))
                     }
@@ -183,8 +255,6 @@ impl Nip34WritePolicy {
     /// * `event` - The state event to validate
     /// * `is_synced` - True if this event came from proactive sync (vs user-submitted)
     async fn handle_state(&self, event: &Event, is_synced: bool) -> WritePolicyResult {
-        let event_id_str = event.id.to_bech32().unwrap_or_else(|_| event.id.to_hex());
-
         match self.state_policy.validate(event) {
             StateResult::Accept => {
                 // Process state alignment asynchronously
@@ -195,7 +265,19 @@ impl Nip34WritePolicy {
                 {
                     Ok(poilicy_result) => poilicy_result,
                     Err(e) => {
-                        tracing::warn!("Failed to process state event {}: {}", event_id_str, e);
+                        let npub = event.pubkey.to_bech32().unwrap_or_else(|_| event.pubkey.to_hex());
+                        let event_id_short = &event.id.to_hex()[..12];
+                        // Try to extract repo identifier from 'd' tag even if parsing failed
+                        let repo = Self::extract_identifier_from_event(event);
+                        // Structured log for migration scripts
+                        tracing::warn!(
+                            "[PARSE_FAIL] kind={} event_id={}... reason=\"{}\" repo={} npub={}",
+                            event.kind.as_u16(),
+                            event_id_short,
+                            e,
+                            repo,
+                            npub
+                        );
                         // reject if processing failed
                         WritePolicyResult::Reject {
                             status: false,
@@ -205,7 +287,19 @@ impl Nip34WritePolicy {
                 }
             }
             StateResult::Reject(reason) => {
-                tracing::warn!("Rejected repository state {}: {}", event_id_str, reason);
+                let npub = event.pubkey.to_bech32().unwrap_or_else(|_| event.pubkey.to_hex());
+                let event_id_short = &event.id.to_hex()[..12];
+                // Try to extract repo identifier from 'd' tag even if parsing failed
+                let repo = Self::extract_identifier_from_event(event);
+                // Structured log for migration scripts
+                tracing::warn!(
+                    "[PARSE_FAIL] kind={} event_id={}... reason=\"{}\" repo={} npub={}",
+                    event.kind.as_u16(),
+                    event_id_short,
+                    reason,
+                    repo,
+                    npub
+                );
                 WritePolicyResult::reject(reason)
             }
         }
@@ -323,11 +417,22 @@ impl Nip34WritePolicy {
             }
             Err(e) => {
                 // Error checking git data - reject event
-                tracing::warn!(
-                    "Failed to check git data for PR event {}: {}",
-                    event_id_str,
-                    e
-                );
+                let npub = event.pubkey.to_bech32().unwrap_or_else(|_| event.pubkey.to_hex());
+                let event_id_short = &event.id.to_hex()[..12];
+                // Extract ALL repo identifiers from 'a' tags for PR events
+                // (PR events can reference multiple repos when there are multiple maintainers)
+                let repos = Self::extract_repos_from_pr_event(event);
+                // Structured log for migration scripts - log once per repo
+                for repo in &repos {
+                    tracing::warn!(
+                        "[PARSE_FAIL] kind={} event_id={}... reason=\"git data check failed: {}\" repo={} npub={}",
+                        event.kind.as_u16(),
+                        event_id_short,
+                        e,
+                        repo,
+                        npub
+                    );
+                }
                 WritePolicyResult::reject(format!("Failed to check git data: {}", e))
             }
         }
diff --git a/src/purgatory/mod.rs b/src/purgatory/mod.rs
index 47798a6..8b75351 100644
--- a/src/purgatory/mod.rs
+++ b/src/purgatory/mod.rs
@@ -21,6 +21,7 @@ pub use types::{PrPurgatoryEntry, RefPair, RefUpdate, StatePurgatoryEntry};
 
 use dashmap::DashMap;
 use nostr_sdk::prelude::*;
+use nostr_sdk::ToBech32;
 use serde::{Deserialize, Serialize};
 use std::collections::HashMap;
 use std::collections::HashSet;
@@ -608,6 +609,9 @@ impl Purgatory {
     /// prevent infinite re-sync loops. Events that expire without finding git data
     /// will be filtered out during future negentropy/REQ sync operations.
     ///
+    /// Emits structured `[PURGATORY_EXPIRED]` log entries for each expired event
+    /// to support migration scripts and operational monitoring.
+    ///
     /// # Returns
     /// Tuple of (num_state_removed, num_pr_removed)
     pub fn cleanup(&self) -> (usize, usize) {
@@ -615,18 +619,24 @@ impl Purgatory {
         let mut state_removed = 0;
 
         // Remove expired state events and mark them as expired
-        self.state_events.retain(|_, entries| {
+        self.state_events.retain(|identifier, entries| {
             let original_len = entries.len();
-            // Collect event IDs before removing
-            let expired_ids: Vec<EventId> = entries
-                .iter()
-                .filter(|entry| entry.expires_at <= now)
-                .map(|entry| entry.event.id)
-                .collect();
 
-            // Mark as expired to prevent re-sync
-            for event_id in expired_ids {
-                self.mark_expired(event_id);
+            // Log and collect expired entries before removing
+            for entry in entries.iter().filter(|e| e.expires_at <= now) {
+                let npub = entry.author.to_bech32().unwrap_or_else(|_| entry.author.to_hex());
+                let event_id_short = &entry.event.id.to_hex()[..12];
+
+                // Structured log for migration scripts
+                tracing::warn!(
+                    "[PURGATORY_EXPIRED] repo={} npub={} event_id={}... kind={} reason=\"git data not received within 30 minutes\"",
+                    identifier,
+                    npub,
+                    event_id_short,
+                    entry.event.kind.as_u16()
+                );
+
+                self.mark_expired(entry.event.id);
             }
 
             // Remove expired entries
@@ -636,21 +646,80 @@ impl Purgatory {
         });
 
         // Remove expired PR events and mark them as expired
-        let expired_prs: Vec<(String, Option<EventId>)> = self
+        let expired_prs: Vec<_> = self
             .pr_events
             .iter()
             .filter(|entry| entry.value().expires_at <= now)
             .map(|entry| {
-                let event_id = entry.value().event.as_ref().map(|e| e.id);
-                (entry.key().clone(), event_id)
+                let pr_entry = entry.value();
+                let event_id_str = entry.key().clone();
+                let event_opt = pr_entry.event.clone();
+                let commit = pr_entry.commit.clone();
+                (event_id_str, event_opt, commit)
             })
             .collect();
 
         let pr_removed = expired_prs.len();
-        for (event_id_str, event_id_opt) in expired_prs {
-            // Mark actual PR events as expired (not placeholders)
-            if let Some(event_id) = event_id_opt {
-                self.mark_expired(event_id);
+        for (event_id_str, event_opt, commit) in expired_prs {
+            // Log structured entry for PR events (not placeholders)
+            if let Some(ref event) = event_opt {
+                let npub = event.pubkey.to_bech32().unwrap_or_else(|_| event.pubkey.to_hex());
+                let event_id_short = &event.id.to_hex()[..12];
+
+                // Extract ALL repo identifiers from 'a' tags
+                // (PR events can reference multiple repos when there are multiple maintainers)
+                let repos: Vec<String> = event
+                    .tags
+                    .iter()
+                    .filter_map(|tag| {
+                        let tag_vec = tag.clone().to_vec();
+                        if tag_vec.len() >= 2 && tag_vec[0] == "a" && tag_vec[1].starts_with("30617:") {
+                            // Format: 30617:<owner_pubkey>:<identifier>
+                            let parts: Vec<&str> = tag_vec[1].split(':').collect();
+                            if parts.len() >= 3 {
+                                Some(parts[2].to_string())
+                            } else {
+                                None
+                            }
+                        } else {
+                            None
+                        }
+                    })
+                    .collect();
+
+                // Deduplicate while preserving order
+                let mut seen = std::collections::HashSet::new();
+                let unique_repos: Vec<String> = repos
+                    .into_iter()
+                    .filter(|r| seen.insert(r.clone()))
+                    .collect();
+
+                let repos_to_log = if unique_repos.is_empty() {
+                    vec!["unknown".to_string()]
+                } else {
+                    unique_repos
+                };
+
+                // Structured log for migration scripts - log once per repo
+                for repo in &repos_to_log {
+                    tracing::warn!(
+                        "[PURGATORY_EXPIRED] repo={} npub={} event_id={}... kind={} commit={} reason=\"git data not received within 30 minutes\"",
+                        repo,
+                        npub,
+                        event_id_short,
+                        event.kind.as_u16(),
+                        &commit[..commit.len().min(12)]
+                    );
+                }
+
+                self.mark_expired(event.id);
+            } else {
+                // Placeholder (git data arrived first, but PR event never came)
+                tracing::debug!(
+                    "[PURGATORY_EXPIRED] placeholder event_id={} commit={} reason=\"PR event not received within 30 minutes\"",
+                    &event_id_str[..event_id_str.len().min(12)],
+                    &commit[..commit.len().min(12)]
+                );
             }
             self.pr_events.remove(&event_id_str);
         }