diff --git a/server/src/analyze/auto_trigger.rs b/server/src/analyze/auto_trigger.rs
new file mode 100644
index 0000000..556adcf
--- /dev/null
+++ b/server/src/analyze/auto_trigger.rs
@@ -0,0 +1,531 @@
+//! Opportunistic auto-trigger for LLM analysis.
+//!
+//! Called by the `/web/cases` and `/web/cases/{id}` handlers on every
+//! request. The SSE-driven `location.reload()` in the UI turns every
+//! relevant state change (upload, transcript, document) into a fresh
+//! handler invocation, so no background timer is needed.
+//!
+//! The hot path is a pure `evaluate_case` pre-condition check; the
+//! `try_enqueue` wrapper performs the actual side effects.
+
+use std::path::Path;
+use std::sync::Arc;
+use std::time::SystemTime;
+
+use serde::{Deserialize, Serialize};
+use time::OffsetDateTime;
+use time::format_description::well_known::Rfc3339;
+use tokio::io::AsyncWriteExt;
+use tracing::warn;
+
+use super::{ANALYSIS_INPUT_FILE, AnalysisInput, AnalyzeJob, AnalyzeSender, DOCUMENT_FILE};
+use crate::config::Config;
+use crate::events::{self, CaseEventKind, EventSender};
+use crate::routes::case_actions::build_analysis_input;
+
+/// Filename of the per-case failure marker. Written by the worker on
+/// error, deleted on success. Presence with a matching
+/// `last_recording_mtime` tells us "already tried this exact input, do
+/// not retry until the input changes".
+pub const FAILURE_MARKER_FILE: &str = ".analysis_failed.json";
+
+/// Persistent failure record. JSON so it is human-readable and carries
+/// a reason for post-mortem.
+#[derive(Debug, Serialize, Deserialize)]
+pub struct FailureMarker {
+    pub last_recording_mtime: String,
+    pub reason: String,
+    pub failed_at: String,
+}
+
+/// Outcome of the pre-condition check. `Skip` carries a static string so
+/// the common "nothing to do" path allocates nothing.
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub enum AutoDecision {
+    Enqueue,
+    Skip(&'static str),
+}
+
+/// Pure pre-condition check: decide whether this case is due for an
+/// automatic analysis. Does file I/O but no channel sends and no
+/// state mutations — safe to call redundantly.
+pub async fn evaluate_case(case_dir: &Path) -> AutoDecision {
+    let scan = scan_m4as(case_dir).await;
+
+    if !scan.saw_any {
+        return AutoDecision::Skip("no recordings");
+    }
+    if !scan.all_transcribed {
+        return AutoDecision::Skip("not all transcribed");
+    }
+    let Some(latest_mtime) = scan.latest_mtime else {
+        return AutoDecision::Skip("no recordings");
+    };
+
+    // Any existing analysis_input.json means a job is queued or running.
+    // Worker removes the file on success — next reload re-evaluates.
+    if tokio::fs::try_exists(case_dir.join(ANALYSIS_INPUT_FILE))
+        .await
+        .unwrap_or(false)
+    {
+        return AutoDecision::Skip("job queued");
+    }
+
+    // A failure marker matching the current input signature means we
+    // already tried and the input has not changed since.
+    if let Some(marker) = read_failure_marker(case_dir).await
+        && marker.last_recording_mtime == rfc3339_of(latest_mtime)
+    {
+        return AutoDecision::Skip("previously failed");
+    }
+
+    // Fresh document older than the newest recording → stale, re-analyse.
+    // Fresh document newer or equal → nothing to do.
+    let doc_path = case_dir.join(DOCUMENT_FILE);
+    if let Ok(meta) = tokio::fs::metadata(&doc_path).await
+        && let Ok(doc_mtime) = meta.modified()
+        && doc_mtime >= latest_mtime
+    {
+        return AutoDecision::Skip("analysis current");
+    }
+
+    AutoDecision::Enqueue
+}
+
+/// Evaluate and, on `Enqueue`, prepare and send the job. Returns `true`
+/// iff a job was actually sent. Silent on routine skips; `warn!` only on
+/// actual failures (build_input, write, send).
+pub async fn try_enqueue(
+    case_dir: &Path,
+    tx: &AnalyzeSender,
+    config: &Arc<Config>,
+    events_tx: &EventSender,
+) -> bool {
+    if !config.llm_configured() {
+        return false;
+    }
+
+    match evaluate_case(case_dir).await {
+        AutoDecision::Skip(_) => return false,
+        AutoDecision::Enqueue => {}
+    }
+
+    let input = match build_analysis_input(case_dir).await {
+        Ok(i) => i,
+        Err(e) => {
+            warn!(case = %case_dir.display(), error = ?e, "auto-analyze: build input failed");
+            return false;
+        }
+    };
+
+    // Re-analyse path: delete stale document.md up front so the worker's
+    // "document exists → skip" guard does not short-circuit, and the UI
+    // stops showing the outdated text during the render race.
+    let doc_path = case_dir.join(DOCUMENT_FILE);
+    if let Err(e) = remove_if_exists(&doc_path).await {
+        warn!(case = %case_dir.display(), error = %e, "auto-analyze: remove old doc failed");
+        return false;
+    }
+
+    let input_path = case_dir.join(ANALYSIS_INPUT_FILE);
+    if let Err(e) = write_input_overwrite(&input_path, &input).await {
+        warn!(case = %case_dir.display(), error = %e, "auto-analyze: write input failed");
+        return false;
+    }
+
+    if tx
+        .send(AnalyzeJob {
+            case_dir: case_dir.to_path_buf(),
+        })
+        .is_err()
+    {
+        warn!(case = %case_dir.display(), "auto-analyze: send failed (worker gone)");
+        return false;
+    }
+
+    events::emit(
+        events_tx,
+        events::user_slug_of(case_dir),
+        events::case_id_of(case_dir),
+        CaseEventKind::AnalysisQueued,
+    );
+    true
+}
+
+/// Iterate over every non-deleted UUID-named case directory under
+/// `user_root` and run `try_enqueue` on each. Safe to call on every
+/// `/web/cases` render — skips are cheap filesystem stats.
+pub async fn try_enqueue_all_for_user(
+    user_root: &Path,
+    tx: &AnalyzeSender,
+    config: &Arc<Config>,
+    events_tx: &EventSender,
+) {
+    let Ok(mut entries) = tokio::fs::read_dir(user_root).await else {
+        return;
+    };
+    while let Ok(Some(entry)) = entries.next_entry().await {
+        let Ok(name) = entry.file_name().into_string() else {
+            continue;
+        };
+        if uuid::Uuid::parse_str(&name).is_err() {
+            continue;
+        }
+        let case_path = entry.path();
+        if !case_path.is_dir() {
+            continue;
+        }
+        if crate::paths::is_deleted(&case_path).await {
+            continue;
+        }
+        try_enqueue(&case_path, tx, config, events_tx).await;
+    }
+}
+
+/// Persist a failure marker atomically. Called by the worker after a
+/// terminal failure. `last_recording_mtime` must equal the value read
+/// from the `AnalysisInput` so `evaluate_case` can later detect an
+/// unchanged input.
+pub async fn write_failure_marker(
+    case_dir: &Path,
+    last_recording_mtime: &str,
+    reason: &str,
+) -> std::io::Result<()> {
+    let marker = FailureMarker {
+        last_recording_mtime: last_recording_mtime.to_owned(),
+        reason: reason.to_owned(),
+        failed_at: doctate_common::now_rfc3339(),
+    };
+    let bytes = serde_json::to_vec_pretty(&marker)
+        .map_err(|e| std::io::Error::new(std::io::ErrorKind::InvalidData, e))?;
+    let path = case_dir.join(FAILURE_MARKER_FILE);
+    let tmp = path.with_extension("json.tmp");
+    let mut f = tokio::fs::File::create(&tmp).await?;
+    f.write_all(&bytes).await?;
+    f.sync_all().await?;
+    drop(f);
+    tokio::fs::rename(&tmp, &path).await
+}
+
+/// Best-effort delete. Called by the worker after a successful run so
+/// the next `evaluate_case` does not mistake a resolved failure for a
+/// pending one.
+pub async fn remove_failure_marker(case_dir: &Path) {
+    let _ = tokio::fs::remove_file(case_dir.join(FAILURE_MARKER_FILE)).await;
+}
+
+struct M4aScan {
+    saw_any: bool,
+    all_transcribed: bool,
+    latest_mtime: Option<SystemTime>,
+}
+
+/// One-pass directory walk collecting everything `evaluate_case` needs.
+/// `.m4a.failed` entries are skipped because they did not contribute a
+/// transcript and will not contribute one in the future.
+async fn scan_m4as(case_dir: &Path) -> M4aScan {
+    let mut scan = M4aScan {
+        saw_any: false,
+        all_transcribed: true,
+        latest_mtime: None,
+    };
+
+    let mut entries = match tokio::fs::read_dir(case_dir).await {
+        Ok(r) => r,
+        Err(_) => return scan,
+    };
+
+    while let Ok(Some(entry)) = entries.next_entry().await {
+        let Ok(name) = entry.file_name().into_string() else {
+            continue;
+        };
+        if !name.ends_with(".m4a") {
+            continue;
+        }
+        scan.saw_any = true;
+
+        if let Ok(meta) = entry.metadata().await
+            && let Ok(mtime) = meta.modified()
+        {
+            scan.latest_mtime = Some(match scan.latest_mtime {
+                Some(prev) if prev >= mtime => prev,
+                _ => mtime,
+            });
+        }
+
+        let transcript = entry.path().with_extension("transcript.txt");
+        if !tokio::fs::try_exists(&transcript).await.unwrap_or(false) {
+            scan.all_transcribed = false;
+        }
+    }
+
+    scan
+}
+
+async fn read_failure_marker(case_dir: &Path) -> Option<FailureMarker> {
+    let bytes = tokio::fs::read(case_dir.join(FAILURE_MARKER_FILE))
+        .await
+        .ok()?;
+    serde_json::from_slice(&bytes).ok()
+}
+
+async fn remove_if_exists(path: &Path) -> std::io::Result<()> {
+    match tokio::fs::remove_file(path).await {
+        Ok(_) => Ok(()),
+        Err(e) if e.kind() == std::io::ErrorKind::NotFound => Ok(()),
+        Err(e) => Err(e),
+    }
+}
+
+/// Overwrite-capable sibling of `case_actions::write_input_create_new`.
+/// Auto-trigger re-analyses may legitimately replace an existing input
+/// (e.g. a new recording arrived between two reloads while the previous
+/// job was still queued). `.tmp` + fsync + rename keeps it atomic.
+async fn write_input_overwrite(path: &Path, input: &AnalysisInput) -> std::io::Result<()> {
+    let bytes = serde_json::to_vec_pretty(input)
+        .map_err(|e| std::io::Error::new(std::io::ErrorKind::InvalidData, e))?;
+    let tmp = path.with_extension("json.tmp");
+    let mut f = tokio::fs::File::create(&tmp).await?;
+    f.write_all(&bytes).await?;
+    f.sync_all().await?;
+    drop(f);
+    tokio::fs::rename(&tmp, path).await
+}
+
+/// Format an mtime in the same RFC3339 shape that
+/// `case_actions::build_analysis_input` writes, so equality comparison
+/// against a stored marker is string-exact.
+fn rfc3339_of(t: SystemTime) -> String {
+    OffsetDateTime::from(t).format(&Rfc3339).unwrap_or_default()
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use filetime::{FileTime, set_file_mtime};
+    use std::time::Duration;
+    use tempfile::TempDir;
+    use tokio::fs;
+
+    async fn touch(path: &std::path::Path) {
+        fs::write(path, b"").await.unwrap();
+    }
+
+    fn set_mtime(path: &std::path::Path, t: SystemTime) {
+        set_file_mtime(path, FileTime::from_system_time(t)).unwrap();
+    }
+
+    #[tokio::test]
+    async fn empty_dir_skips() {
+        let dir = TempDir::new().unwrap();
+        assert_eq!(
+            evaluate_case(dir.path()).await,
+            AutoDecision::Skip("no recordings")
+        );
+    }
+
+    #[tokio::test]
+    async fn missing_transcript_skips() {
+        let dir = TempDir::new().unwrap();
+        touch(&dir.path().join("2026-01-01T10-00-00Z.m4a")).await;
+        touch(&dir.path().join("2026-01-01T10-00-00Z.transcript.txt")).await;
+        touch(&dir.path().join("2026-01-01T11-00-00Z.m4a")).await;
+        assert_eq!(
+            evaluate_case(dir.path()).await,
+            AutoDecision::Skip("not all transcribed")
+        );
+    }
+
+    #[tokio::test]
+    async fn all_transcribed_no_document_enqueues() {
+        let dir = TempDir::new().unwrap();
+        touch(&dir.path().join("2026-01-01T10-00-00Z.m4a")).await;
+        touch(&dir.path().join("2026-01-01T10-00-00Z.transcript.txt")).await;
+        assert_eq!(evaluate_case(dir.path()).await, AutoDecision::Enqueue);
+    }
+
+    #[tokio::test]
+    async fn document_newer_than_recordings_skips() {
+        let dir = TempDir::new().unwrap();
+        let m4a = dir.path().join("2026-01-01T10-00-00Z.m4a");
+        touch(&m4a).await;
+        touch(&dir.path().join("2026-01-01T10-00-00Z.transcript.txt")).await;
+        let doc = dir.path().join(DOCUMENT_FILE);
+        touch(&doc).await;
+
+        let base = SystemTime::UNIX_EPOCH + Duration::from_secs(1_700_000_000);
+        set_mtime(&m4a, base);
+        set_mtime(&doc, base + Duration::from_secs(60));
+
+        assert_eq!(
+            evaluate_case(dir.path()).await,
+            AutoDecision::Skip("analysis current")
+        );
+    }
+
+    #[tokio::test]
+    async fn document_older_than_recordings_enqueues() {
+        let dir = TempDir::new().unwrap();
+        let m4a = dir.path().join("2026-01-01T10-00-00Z.m4a");
+        touch(&m4a).await;
+        touch(&dir.path().join("2026-01-01T10-00-00Z.transcript.txt")).await;
+        let doc = dir.path().join(DOCUMENT_FILE);
+        touch(&doc).await;
+
+        let base = SystemTime::UNIX_EPOCH + Duration::from_secs(1_700_000_000);
+        set_mtime(&doc, base);
+        set_mtime(&m4a, base + Duration::from_secs(60));
+
+        assert_eq!(evaluate_case(dir.path()).await, AutoDecision::Enqueue);
+    }
+
+    #[tokio::test]
+    async fn analysis_input_present_skips() {
+        let dir = TempDir::new().unwrap();
+        touch(&dir.path().join("2026-01-01T10-00-00Z.m4a")).await;
+        touch(&dir.path().join("2026-01-01T10-00-00Z.transcript.txt")).await;
+        touch(&dir.path().join(ANALYSIS_INPUT_FILE)).await;
+        assert_eq!(
+            evaluate_case(dir.path()).await,
+            AutoDecision::Skip("job queued")
+        );
+    }
+
+    #[tokio::test]
+    async fn failure_marker_matching_mtime_skips() {
+        let dir = TempDir::new().unwrap();
+        let m4a = dir.path().join("2026-01-01T10-00-00Z.m4a");
+        touch(&m4a).await;
+        touch(&dir.path().join("2026-01-01T10-00-00Z.transcript.txt")).await;
+
+        let base = SystemTime::UNIX_EPOCH + Duration::from_secs(1_700_000_000);
+        set_mtime(&m4a, base);
+
+        let marker = FailureMarker {
+            last_recording_mtime: rfc3339_of(base),
+            reason: "test".into(),
+            failed_at: "2026-01-01T10-05-00Z".into(),
+        };
+        fs::write(
+            dir.path().join(FAILURE_MARKER_FILE),
+            serde_json::to_vec(&marker).unwrap(),
+        )
+        .await
+        .unwrap();
+
+        assert_eq!(
+            evaluate_case(dir.path()).await,
+            AutoDecision::Skip("previously failed")
+        );
+    }
+
+    #[tokio::test]
+    async fn failure_marker_stale_mtime_enqueues() {
+        let dir = TempDir::new().unwrap();
+        let m4a = dir.path().join("2026-01-01T10-00-00Z.m4a");
+        touch(&m4a).await;
+        touch(&dir.path().join("2026-01-01T10-00-00Z.transcript.txt")).await;
+
+        let base = SystemTime::UNIX_EPOCH + Duration::from_secs(1_700_000_000);
+        set_mtime(&m4a, base);
+
+        // Marker records an older mtime → input has since changed.
+        let marker = FailureMarker {
+            last_recording_mtime: rfc3339_of(base - Duration::from_secs(3600)),
+            reason: "test".into(),
+            failed_at: "2025-12-31T23-00-00Z".into(),
+        };
+        fs::write(
+            dir.path().join(FAILURE_MARKER_FILE),
+            serde_json::to_vec(&marker).unwrap(),
+        )
+        .await
+        .unwrap();
+
+        assert_eq!(evaluate_case(dir.path()).await, AutoDecision::Enqueue);
+    }
+
+    #[tokio::test]
+    async fn m4a_failed_is_ignored() {
+        let dir = TempDir::new().unwrap();
+        // Only .m4a.failed present — counts as "no usable recordings".
+        touch(&dir.path().join("2026-01-01T10-00-00Z.m4a.failed")).await;
+        assert_eq!(
+            evaluate_case(dir.path()).await,
+            AutoDecision::Skip("no recordings")
+        );
+    }
+
+    #[tokio::test]
+    async fn try_enqueue_all_sends_only_eligible_cases() {
+        use crate::analyze::channel as analyze_channel;
+        use crate::config::Config;
+        use crate::events::channel as events_channel;
+
+        let user_root = TempDir::new().unwrap();
+
+        // Eligible: all transcribed, no document, plausible content.
+        let eligible_id = "11111111-1111-1111-1111-111111111111";
+        let eligible = user_root.path().join(eligible_id);
+        fs::create_dir_all(&eligible).await.unwrap();
+        fs::write(eligible.join("2026-01-01T10-00-00Z.m4a"), b"fake")
+            .await
+            .unwrap();
+        fs::write(
+            eligible.join("2026-01-01T10-00-00Z.transcript.txt"),
+            b"patient mit brustschmerz",
+        )
+        .await
+        .unwrap();
+
+        // Not eligible: has a fresh document.
+        let current_id = "22222222-2222-2222-2222-222222222222";
+        let current = user_root.path().join(current_id);
+        fs::create_dir_all(&current).await.unwrap();
+        let m4a = current.join("2026-01-01T10-00-00Z.m4a");
+        fs::write(&m4a, b"fake").await.unwrap();
+        fs::write(
+            current.join("2026-01-01T10-00-00Z.transcript.txt"),
+            b"stable",
+        )
+        .await
+        .unwrap();
+        let doc = current.join(DOCUMENT_FILE);
+        fs::write(&doc, b"doc").await.unwrap();
+        let base = SystemTime::UNIX_EPOCH + Duration::from_secs(1_700_000_000);
+        set_mtime(&m4a, base);
+        set_mtime(&doc, base + Duration::from_secs(60));
+
+        // Ignored: non-UUID directory name.
+        let junk = user_root.path().join("not-a-uuid");
+        fs::create_dir_all(&junk).await.unwrap();
+        fs::write(junk.join("2026-01-01T10-00-00Z.m4a"), b"fake")
+            .await
+            .unwrap();
+        fs::write(junk.join("2026-01-01T10-00-00Z.transcript.txt"), b"x")
+            .await
+            .unwrap();
+
+        let (tx, mut rx) = analyze_channel();
+        let events_tx = events_channel();
+        let mut cfg = Config::test_default();
+        cfg.llm_url = "http://localhost:9999".into();
+        cfg.llm_model = "test".into();
+        let cfg = Arc::new(cfg);
+
+        try_enqueue_all_for_user(user_root.path(), &tx, &cfg, &events_tx).await;
+
+        // Drop the sender half so recv closes after draining.
+        drop(tx);
+        let mut received = Vec::new();
+        while let Some(job) = rx.recv().await {
+            received.push(job.case_dir);
+        }
+        assert_eq!(received.len(), 1, "expected exactly one enqueued job");
+        assert!(
+            received[0].ends_with(eligible_id),
+            "expected eligible case, got {}",
+            received[0].display()
+        );
+    }
+}
diff --git a/server/src/analyze/mod.rs b/server/src/analyze/mod.rs
index 2ed90ae..8a8781d 100644
--- a/server/src/analyze/mod.rs
+++ b/server/src/analyze/mod.rs
@@ -3,6 +3,7 @@ use std::path::PathBuf;
 use serde::{Deserialize, Serialize};
 use tokio::sync::mpsc;
 
+pub mod auto_trigger;
 pub mod llm;
 pub mod prompt;
 pub mod recovery;
diff --git a/server/src/analyze/worker.rs b/server/src/analyze/worker.rs
index 960c2c6..1ceca82 100644
--- a/server/src/analyze/worker.rs
+++ b/server/src/analyze/worker.rs
@@ -5,7 +5,9 @@ use std::time::Duration;
 use tokio::io::AsyncWriteExt;
 use tracing::{error, info, warn};
 
-use super::{ANALYSIS_INPUT_FILE, AnalysisInput, AnalyzeReceiver, DOCUMENT_FILE, llm, prompt};
+use super::{
+    ANALYSIS_INPUT_FILE, AnalysisInput, AnalyzeReceiver, DOCUMENT_FILE, auto_trigger, llm, prompt,
+};
 use crate::config::Config;
 use crate::events::{self, CaseEventKind, EventSender};
 use crate::gazetteer::Gazetteer;
@@ -69,11 +71,18 @@ async fn process(
         let stub = b"_Keine verwertbaren Aufnahmen (alle Aufnahmen still)._\n";
         if let Err(e) = write_atomic(&document_path, stub).await {
             error!(path = %document_path.display(), error = %e, "writing stub document failed");
+            let _ = auto_trigger::write_failure_marker(
+                case_dir,
+                &input.last_recording_mtime,
+                &format!("stub write: {e}"),
+            )
+            .await;
             return;
         }
         if let Err(e) = tokio::fs::remove_file(&input_path).await {
             warn!(path = %input_path.display(), error = %e, "removing analysis input failed");
         }
+        auto_trigger::remove_failure_marker(case_dir).await;
         info!(case = %case_dir.display(), "analysis done (stub, no recordings)");
         events::emit(
             events_tx,
@@ -117,6 +126,12 @@ async fn process(
             // Do not log the response body — LlmError::Display is already
             // redacted, but reinforce the rule here for future readers.
             error!(case = %case_dir.display(), error = %e, "llm call failed");
+            let _ = auto_trigger::write_failure_marker(
+                case_dir,
+                &input.last_recording_mtime,
+                &format!("llm: {e}"),
+            )
+            .await;
             return;
         }
     };
@@ -128,6 +143,12 @@ async fn process(
 
     if let Err(e) = write_atomic(&document_path, document.as_bytes()).await {
         error!(path = %document_path.display(), error = %e, "writing document failed");
+        let _ = auto_trigger::write_failure_marker(
+            case_dir,
+            &input.last_recording_mtime,
+            &format!("write document: {e}"),
+        )
+        .await;
         return;
     }
 
@@ -137,6 +158,7 @@ async fn process(
     if let Err(e) = tokio::fs::remove_file(&input_path).await {
         warn!(path = %input_path.display(), error = %e, "removing analysis input failed");
     }
+    auto_trigger::remove_failure_marker(case_dir).await;
 
     info!(
         case = %case_dir.display(),
diff --git a/server/src/error.rs b/server/src/error.rs
index 8a60ae2..01e0111 100644
--- a/server/src/error.rs
+++ b/server/src/error.rs
@@ -2,6 +2,7 @@ use axum::http::StatusCode;
 use axum::response::{IntoResponse, Response};
 use serde_json::json;
 
+#[derive(Debug)]
 pub enum AppError {
     Unauthorized,
     BadRequest(String),
diff --git a/server/src/routes/mod.rs b/server/src/routes/mod.rs
index e45c558..8f08e92 100644
--- a/server/src/routes/mod.rs
+++ b/server/src/routes/mod.rs
@@ -1,5 +1,5 @@
 mod bulk;
-mod case_actions;
+pub(crate) mod case_actions;
 mod debug;
 mod events;
 mod health;
diff --git a/server/src/routes/user_web.rs b/server/src/routes/user_web.rs
index 49b0ecb..9e72960 100644
--- a/server/src/routes/user_web.rs
+++ b/server/src/routes/user_web.rs
@@ -10,11 +10,14 @@ use tracing::{info, warn};
 use time::{Date, OffsetDateTime, format_description::well_known::Rfc3339};
 
 use crate::PipelineState;
-use crate::analyze::{ANALYSIS_INPUT_FILE, DOCUMENT_FILE, recovery as analyze_recovery};
+use crate::analyze::{
+    ANALYSIS_INPUT_FILE, DOCUMENT_FILE, auto_trigger, recovery as analyze_recovery,
+};
 use crate::auth::AuthenticatedWebUser;
 use crate::case_id::{CaseId, CaseIdPath};
 use crate::config::Config;
 use crate::error::AppError;
+use crate::events::EventSender;
 use crate::routes::case_actions::read_document;
 use crate::routes::web::{RecordingView, scan_recordings};
 use crate::transcribe::recovery as transcribe_recovery;
@@ -228,9 +231,16 @@ pub async fn handle_my_cases(
     user: AuthenticatedWebUser,
     State(config): State<Arc<Config>>,
     State(pipeline): State<PipelineState>,
+    State(events_tx): State<EventSender>,
 ) -> Result<Html<String>, AppError> {
     let user_root = config.data_path.join(&user.slug);
     pipeline.heal_orphans_if_idle(&user_root, &user.slug).await;
+    // Auto-analysis: hand every eligible case to the worker before we
+    // render. The common case is "nothing to do" and costs a handful of
+    // stat-calls per case; actual enqueues happen only when pre-conditions
+    // flip (new transcripts in, stale document, ...).
+    auto_trigger::try_enqueue_all_for_user(&user_root, &pipeline.analyze_tx, &config, &events_tx)
+        .await;
 
     let busy = pipeline.analyze_busy.0.load(Ordering::Acquire);
     let cases = scan_user_cases(&config, &user.slug, busy).await;
@@ -263,6 +273,7 @@ pub async fn handle_case_page(
     user: AuthenticatedWebUser,
     State(config): State<Arc<Config>>,
     State(pipeline): State<PipelineState>,
+    State(events_tx): State<EventSender>,
     CaseIdPath(case_id): CaseIdPath,
 ) -> Result<Html<String>, AppError> {
     let user_root = config.data_path.join(&user.slug);
@@ -275,6 +286,10 @@ pub async fn handle_case_page(
         "case page (possible IDOR probe)",
     )
     .await?;
+    // Auto-analysis trigger for deep-link navigation: same evaluation as
+    // the list view. Document render below still wins the race if the
+    // worker happens to finish synchronously.
+    auto_trigger::try_enqueue(&case_dir, &pipeline.analyze_tx, &config, &events_tx).await;
     let case_id_str = case_id.to_string();
     info!(slug = %user.slug, case_id = %case_id, "case page viewed");
 
diff --git a/server/templates/case_page.html b/server/templates/case_page.html
index e23b379..18c5ab2 100644
--- a/server/templates/case_page.html
+++ b/server/templates/case_page.html
@@ -157,6 +157,10 @@ try {
     timer = setTimeout(() => location.reload(), 300);
   };
   const es = new EventSource('/web/events');
+  // Release the socket-pool slot on navigation. Without this, Chrome
+  // keeps the SSE connection "draining" after unload; six rapid nav
+  // cycles exhaust the 6-per-origin pool and stall further requests.
+  window.addEventListener('pagehide', () => es.close());
   es.addEventListener('case', (msg) => {
     let evt;
     try { evt = JSON.parse(msg.data); } catch (_) { return; }
diff --git a/server/templates/case_recordings.html b/server/templates/case_recordings.html
index 9c83d4d..d260c48 100644
--- a/server/templates/case_recordings.html
+++ b/server/templates/case_recordings.html
@@ -275,6 +275,10 @@ try {
     }, 300);
   };
   const es = new EventSource('/web/events');
+  // Release the socket-pool slot on navigation. Without this, Chrome
+  // keeps the SSE connection "draining" after unload; six rapid nav
+  // cycles exhaust the 6-per-origin pool and stall further requests.
+  window.addEventListener('pagehide', () => es.close());
   es.addEventListener('case', (msg) => {
     let evt;
     try { evt = JSON.parse(msg.data); } catch (_) { return; }
diff --git a/server/templates/my_cases.html b/server/templates/my_cases.html
index 113331f..6dd150f 100644
--- a/server/templates/my_cases.html
+++ b/server/templates/my_cases.html
@@ -162,6 +162,10 @@ try {
     timer = setTimeout(() => location.reload(), 300);
   };
   const es = new EventSource('/web/events');
+  // Release the socket-pool slot on navigation. Without this, Chrome
+  // keeps the SSE connection "draining" after unload; six rapid nav
+  // cycles exhaust the 6-per-origin pool and stall further requests.
+  window.addEventListener('pagehide', () => es.close());
   es.addEventListener('case', () => scheduleReload());
 })();
 </script>