diff --git a/lib/crates/fabro-cli/src/commands/artifact/cp.rs b/lib/crates/fabro-cli/src/commands/artifact/cp.rs
index dba10bd53..b1e8e7304 100644
--- a/lib/crates/fabro-cli/src/commands/artifact/cp.rs
+++ b/lib/crates/fabro-cli/src/commands/artifact/cp.rs
@@ -141,7 +141,8 @@ async fn write_artifact_file(
     dest_file: &Path,
 ) -> Result<()> {
     if let Some(parent) = dest_file.parent() {
-        std::fs::create_dir_all(parent)?;
+        std::fs::create_dir_all(parent)
+            .with_context(|| format!("creating directory {}", parent.display()))?;
     }
     let bytes = client
         .download_stage_artifact(run_id, &entry.stage_id, &entry.relative_path)
diff --git a/lib/crates/fabro-cli/src/commands/graph.rs b/lib/crates/fabro-cli/src/commands/graph.rs
index 12a873dc8..a16001cc5 100644
--- a/lib/crates/fabro-cli/src/commands/graph.rs
+++ b/lib/crates/fabro-cli/src/commands/graph.rs
@@ -1,6 +1,6 @@
 use std::io::Write;
 
-use anyhow::bail;
+use anyhow::{Context, bail};
 use fabro_api::types;
 use fabro_config::load::load_settings_user;
 use fabro_config::user::active_settings_path;
@@ -62,7 +62,8 @@ pub(crate) async fn run(
         .await?;
 
     if let Some(ref output_path) = args.output {
-        std::fs::write(output_path, &rendered)?;
+        std::fs::write(output_path, &rendered)
+            .with_context(|| format!("writing rendered graph to {}", output_path.display()))?;
         if cli.output.format == OutputFormat::Json {
             print_json_pretty(&serde_json::json!({
                 "path": absolute_or_current(output_path),
diff --git a/lib/crates/fabro-cli/src/commands/install.rs b/lib/crates/fabro-cli/src/commands/install.rs
index dbf06315e..25fe3d6be 100644
--- a/lib/crates/fabro-cli/src/commands/install.rs
+++ b/lib/crates/fabro-cli/src/commands/install.rs
@@ -1326,10 +1326,9 @@ fn persist_server_env_secrets(storage_dir: &Path, secrets: &[(String, String)])
         return Ok(());
     }
 
-    envfile::merge_env_file(
-        &Storage::new(storage_dir).server_state().env_path(),
-        secrets.iter().cloned(),
-    )?;
+    let env_path = Storage::new(storage_dir).server_state().env_path();
+    envfile::merge_env_file(&env_path, secrets.iter().cloned())
+        .with_context(|| format!("merging server env secrets into {}", env_path.display()))?;
     Ok(())
 }
 
@@ -1364,14 +1363,18 @@ fn restore_optional_file(path: &Path, previous_contents: Option<&str>) -> Result
     match previous_contents {
         Some(contents) => {
             if let Some(parent) = path.parent() {
-                std::fs::create_dir_all(parent)?;
+                std::fs::create_dir_all(parent)
+                    .with_context(|| format!("creating directory {}", parent.display()))?;
             }
-            std::fs::write(path, contents)?;
+            std::fs::write(path, contents)
+                .with_context(|| format!("restoring {}", path.display()))?;
         }
         None => match std::fs::remove_file(path) {
             Ok(()) => {}
             Err(err) if err.kind() == std::io::ErrorKind::NotFound => {}
-            Err(err) => return Err(err.into()),
+            Err(err) => {
+                return Err(anyhow::Error::new(err).context(format!("removing {}", path.display())));
+            }
         },
     }
 
@@ -1389,7 +1392,8 @@ fn persist_github_install_changes(
     let previous_vault = std::fs::read_to_string(&vault_path).ok();
 
     let result = (|| -> Result<()> {
-        let mut server_env = envfile::read_env_file(&server_env_path)?;
+        let mut server_env = envfile::read_env_file(&server_env_path)
+            .with_context(|| format!("reading env file {}", server_env_path.display()))?;
         for key in &writes.server_env_remove {
             server_env.remove(*key);
         }
@@ -1399,7 +1403,8 @@ fn persist_github_install_changes(
         if server_env.is_empty() {
             restore_optional_file(&server_env_path, None)?;
         } else {
-            envfile::write_env_file(&server_env_path, &server_env)?;
+            envfile::write_env_file(&server_env_path, &server_env)
+                .with_context(|| format!("writing env file {}", server_env_path.display()))?;
         }
 
         let mut vault = Vault::load(vault_path.clone()).map_err(anyhow::Error::from)?;
@@ -1415,7 +1420,14 @@ fn persist_github_install_changes(
                 .map_err(anyhow::Error::from)?;
         }
 
-        std::fs::write(writes.settings_write.path, writes.settings_write.contents)?;
+        std::fs::write(writes.settings_write.path, writes.settings_write.contents).with_context(
+            || {
+                format!(
+                    "writing settings file {}",
+                    writes.settings_write.path.display()
+                )
+            },
+        )?;
         Ok(())
     })();
 
@@ -1467,7 +1479,8 @@ async fn persist_install_outputs_with_settings(
     persist_server_env_secrets(storage_dir, server_env_secrets)?;
 
     if let Some(write) = settings_write {
-        std::fs::write(write.path, write.contents)?;
+        std::fs::write(write.path, write.contents)
+            .with_context(|| format!("writing settings file {}", write.path.display()))?;
     }
 
     let persist_result = persist_vault_secrets_with(
@@ -1482,8 +1495,10 @@ async fn persist_install_outputs_with_settings(
     if let Err(err) = persist_result {
         if let Some(write) = settings_write {
             match write.previous_contents {
-                Some(previous) => std::fs::write(write.path, previous)?,
-                None if write.path.exists() => std::fs::remove_file(write.path)?,
+                Some(previous) => std::fs::write(write.path, previous)
+                    .with_context(|| format!("restoring settings file {}", write.path.display()))?,
+                None if write.path.exists() => std::fs::remove_file(write.path)
+                    .with_context(|| format!("removing settings file {}", write.path.display()))?,
                 None => {}
             }
         }
@@ -1818,7 +1833,8 @@ async fn run_install_inner(
     );
     fabro_util::printerr!(printer, "");
 
-    std::fs::create_dir_all(&fabro_dir)?;
+    std::fs::create_dir_all(&fabro_dir)
+        .with_context(|| format!("creating fabro home directory {}", fabro_dir.display()))?;
 
     {
         let env_path = legacy_env::legacy_env_file_path();
diff --git a/lib/crates/fabro-cli/src/commands/server/record.rs b/lib/crates/fabro-cli/src/commands/server/record.rs
index c98b886f9..560f9d9f7 100644
--- a/lib/crates/fabro-cli/src/commands/server/record.rs
+++ b/lib/crates/fabro-cli/src/commands/server/record.rs
@@ -25,7 +25,8 @@ pub(crate) struct ActiveServerRecord {
 
 pub(crate) fn write_server_record(path: &Path, record: &ServerRecord) -> Result<()> {
     if let Some(parent) = path.parent() {
-        std::fs::create_dir_all(parent)?;
+        std::fs::create_dir_all(parent)
+            .with_context(|| format!("creating server record directory {}", parent.display()))?;
     }
     std::fs::write(path, serde_json::to_string_pretty(record)?)
         .with_context(|| format!("Failed to write server metadata to {}", path.display()))
diff --git a/lib/crates/fabro-cli/src/commands/server/start.rs b/lib/crates/fabro-cli/src/commands/server/start.rs
index ed723fcef..ceab81a41 100644
--- a/lib/crates/fabro-cli/src/commands/server/start.rs
+++ b/lib/crates/fabro-cli/src/commands/server/start.rs
@@ -1,7 +1,7 @@
 use std::path::{Path, PathBuf};
 use std::time::Duration;
 
-use anyhow::{Result, anyhow, bail};
+use anyhow::{Context, Result, anyhow, bail};
 use chrono::Utc;
 use fabro_config::user::load_settings_config;
 use fabro_config::{Storage, envfile, resolve_server_from_file};
@@ -174,13 +174,33 @@ fn load_or_create_local_dev_token(storage_dir: &Path, home: &Home) -> Result<Str
         .and_then(|entries| entries.get("FABRO_DEV_TOKEN").cloned())
         .filter(|token| dev_token::validate_dev_token_format(token))
     {
-        dev_token::write_dev_token(&home.dev_token_path(), &token)?;
-        dev_token::write_dev_token(&storage.server_state().dev_token_path(), &token)?;
+        dev_token::write_dev_token(&home.dev_token_path(), &token)
+            .with_context(|| format!("writing dev token to {}", home.dev_token_path().display()))?;
+        dev_token::write_dev_token(&storage.server_state().dev_token_path(), &token).with_context(
+            || {
+                format!(
+                    "writing dev token to {}",
+                    storage.server_state().dev_token_path().display()
+                )
+            },
+        )?;
         return Ok(token);
     }
 
-    let token = dev_token::load_or_create_dev_token(&home.dev_token_path())?;
-    dev_token::write_dev_token(&storage.server_state().dev_token_path(), &token)?;
+    let token = dev_token::load_or_create_dev_token(&home.dev_token_path()).with_context(|| {
+        format!(
+            "loading or creating dev token at {}",
+            home.dev_token_path().display()
+        )
+    })?;
+    dev_token::write_dev_token(&storage.server_state().dev_token_path(), &token).with_context(
+        || {
+            format!(
+                "writing dev token to {}",
+                storage.server_state().dev_token_path().display()
+            )
+        },
+    )?;
     Ok(token)
 }
 
@@ -207,7 +227,8 @@ fn load_or_create_local_session_secret(storage_dir: &Path) -> Result<String> {
     }
 
     let secret = session_secret::generate_session_secret();
-    envfile::merge_env_file(&server_env_path, [("SESSION_SECRET", secret.as_str())])?;
+    envfile::merge_env_file(&server_env_path, [("SESSION_SECRET", secret.as_str())])
+        .with_context(|| format!("merging session secret into {}", server_env_path.display()))?;
     Ok(secret)
 }
 
@@ -319,13 +340,17 @@ async fn execute_daemon(
     let server_state = Storage::new(storage_dir).server_state();
     let log_path = server_state.log_path();
     if let Some(parent) = log_path.parent() {
-        std::fs::create_dir_all(parent)?;
+        std::fs::create_dir_all(parent)
+            .with_context(|| format!("creating log directory {}", parent.display()))?;
     }
 
     let record_path = server_state.record_path();
-    let log_file = std::fs::File::create(&log_path)?;
-    let stdout_log = log_file.try_clone()?;
-    let exe = std::env::current_exe()?;
+    let log_file = std::fs::File::create(&log_path)
+        .with_context(|| format!("creating server log file {}", log_path.display()))?;
+    let stdout_log = log_file
+        .try_clone()
+        .with_context(|| format!("cloning server log file handle for {}", log_path.display()))?;
+    let exe = std::env::current_exe().context("resolving current fabro executable path")?;
 
     let mut cmd = TokioCommand::new(&exe);
     cmd.args(["server", "__serve"])
@@ -376,7 +401,9 @@ async fn execute_daemon(
     #[cfg(unix)]
     fabro_proc::pre_exec_setsid(cmd.as_std_mut());
 
-    let mut child = cmd.spawn()?;
+    let mut child = cmd
+        .spawn()
+        .with_context(|| format!("spawning fabro server subprocess {}", exe.display()))?;
 
     if let Ok(Some(status)) = child.try_wait() {
         record::remove_server_record(&record_path);
@@ -464,13 +491,15 @@ fn print_dev_token(printer: Printer, home: &Home, token: &str) {
 async fn acquire_lock(storage_dir: &Path) -> Result<std::fs::File> {
     let lock_path = Storage::new(storage_dir).server_state().lock_path();
     if let Some(parent) = lock_path.parent() {
-        std::fs::create_dir_all(parent)?;
+        std::fs::create_dir_all(parent)
+            .with_context(|| format!("creating server lock directory {}", parent.display()))?;
     }
     let lock_file = std::fs::OpenOptions::new()
         .create(true)
         .write(true)
         .truncate(false)
-        .open(&lock_path)?;
+        .open(&lock_path)
+        .with_context(|| format!("opening server lock file {}", lock_path.display()))?;
 
     let poll_interval = Duration::from_millis(50);
     let timeout = Duration::from_secs(5);
diff --git a/lib/crates/fabro-cli/src/commands/store/dump.rs b/lib/crates/fabro-cli/src/commands/store/dump.rs
index 67764a7d3..018e7775a 100644
--- a/lib/crates/fabro-cli/src/commands/store/dump.rs
+++ b/lib/crates/fabro-cli/src/commands/store/dump.rs
@@ -277,7 +277,9 @@ fn inspect_output_dir(path: &Path) -> Result<OutputDirState> {
             Ok(OutputDirState::ExistingEmpty)
         }
         Err(err) if err.kind() == ErrorKind::NotFound => Ok(OutputDirState::Missing),
-        Err(err) => Err(err.into()),
+        Err(err) => {
+            Err(anyhow::Error::new(err).context(format!("reading metadata for {}", path.display())))
+        }
     }
 }
 
diff --git a/lib/crates/fabro-cli/src/commands/upgrade.rs b/lib/crates/fabro-cli/src/commands/upgrade.rs
index f47a40cac..001cff8ed 100644
--- a/lib/crates/fabro-cli/src/commands/upgrade.rs
+++ b/lib/crates/fabro-cli/src/commands/upgrade.rs
@@ -144,8 +144,10 @@ impl Backend {
                     bail!("download failed: HTTP {}", resp.status());
                 }
                 let bytes = resp.bytes().await?;
-                let mut file = fs::File::create(&dest)?;
-                file.write_all(&bytes)?;
+                let mut file = fs::File::create(&dest)
+                    .with_context(|| format!("creating download file {}", dest.display()))?;
+                file.write_all(&bytes)
+                    .with_context(|| format!("writing download to {}", dest.display()))?;
             }
         }
         Ok(dest)
@@ -231,7 +233,8 @@ fn verify_checksum(path: &Path, expected_hex: &str) -> Result<()> {
     let mut file = std::io::BufReader::new(
         fs::File::open(path).with_context(|| format!("failed to open {}", path.display()))?,
     );
-    std::io::copy(&mut file, &mut hasher)?;
+    std::io::copy(&mut file, &mut hasher)
+        .with_context(|| format!("reading {} for checksum", path.display()))?;
     let computed = format!("{:x}", hasher.finalize());
     // The .sha256 file may contain "hash  filename" or just "hash"
     let expected = expected_hex
@@ -272,10 +275,12 @@ impl UpgradeCheckState {
 
     fn save(&self, path: &Path) -> Result<()> {
         if let Some(parent) = path.parent() {
-            fs::create_dir_all(parent)?;
+            fs::create_dir_all(parent)
+                .with_context(|| format!("creating directory {}", parent.display()))?;
         }
         let json = serde_json::to_string(self)?;
-        fs::write(path, json)?;
+        fs::write(path, json)
+            .with_context(|| format!("writing upgrade check state {}", path.display()))?;
         Ok(())
     }
 }
@@ -365,7 +370,10 @@ pub(crate) async fn run_upgrade(
     let tarball_name = format!("fabro-{triple}.tar.gz");
     let checksum_name = format!("{tarball_name}.sha256");
 
-    let current_exe = std::env::current_exe()?.canonicalize()?;
+    let current_exe = std::env::current_exe()
+        .context("resolving current fabro executable path")?
+        .canonicalize()
+        .context("canonicalizing current fabro executable path")?;
     let exe_dir = current_exe
         .parent()
         .context("could not determine executable directory")?;
@@ -382,7 +390,8 @@ pub(crate) async fn run_upgrade(
     )?;
 
     // Verify SHA256 using streaming hash
-    let checksum_content = fs::read_to_string(&checksum_path)?;
+    let checksum_content = fs::read_to_string(&checksum_path)
+        .with_context(|| format!("reading checksum file {}", checksum_path.display()))?;
     verify_checksum(&tarball_path, &checksum_content)?;
     debug!("SHA256 checksum verified");
 
diff --git a/lib/crates/fabro-cli/src/user_config.rs b/lib/crates/fabro-cli/src/user_config.rs
index 4074284d9..a64cf5c46 100644
--- a/lib/crates/fabro-cli/src/user_config.rs
+++ b/lib/crates/fabro-cli/src/user_config.rs
@@ -1,6 +1,6 @@
 use std::path::{Path, PathBuf};
 
-use anyhow::{Result, bail};
+use anyhow::{Context, Result, bail};
 pub(crate) use fabro_config::user::*;
 use fabro_types::settings::cli::CliTargetSettings;
 use fabro_types::settings::{CliSettings, SettingsLayer};
@@ -208,9 +208,12 @@ pub(crate) fn build_server_client_builder(
     let key_path = fabro_config::expand_tilde(&tls.key);
     let ca_path = fabro_config::expand_tilde(&tls.ca);
 
-    let cert_pem = std::fs::read(&cert_path)?;
-    let key_pem = std::fs::read(&key_path)?;
-    let ca_pem = std::fs::read(&ca_path)?;
+    let cert_pem = std::fs::read(&cert_path)
+        .with_context(|| format!("reading TLS client certificate {}", cert_path.display()))?;
+    let key_pem = std::fs::read(&key_path)
+        .with_context(|| format!("reading TLS client key {}", key_path.display()))?;
+    let ca_pem = std::fs::read(&ca_path)
+        .with_context(|| format!("reading TLS CA certificate {}", ca_path.display()))?;
 
     let mut identity_pem = cert_pem;
     identity_pem.push(b'\n');
diff --git a/lib/crates/fabro-devcontainer/src/compose.rs b/lib/crates/fabro-devcontainer/src/compose.rs
index 6a29213a4..997d65efb 100644
--- a/lib/crates/fabro-devcontainer/src/compose.rs
+++ b/lib/crates/fabro-devcontainer/src/compose.rs
@@ -23,11 +23,15 @@ pub(crate) fn parse_compose(
     compose_path: &Path,
     service_name: &str,
 ) -> Result<ComposeServiceSpec, String> {
-    let contents = std::fs::read_to_string(compose_path)
-        .map_err(|e| format!("failed to read compose file: {e}"))?;
+    let contents = std::fs::read_to_string(compose_path).map_err(|e| {
+        format!(
+            "failed to read compose file {}: {e}",
+            compose_path.display()
+        )
+    })?;
 
-    let doc: serde_yaml::Value =
-        serde_yaml::from_str(&contents).map_err(|e| format!("failed to parse YAML: {e}"))?;
+    let doc: serde_yaml::Value = serde_yaml::from_str(&contents)
+        .map_err(|e| format!("failed to parse YAML {}: {e}", compose_path.display()))?;
 
     let service = doc
         .get("services")
diff --git a/lib/crates/fabro-devcontainer/src/features.rs b/lib/crates/fabro-devcontainer/src/features.rs
index bd88e1ed7..8599e7cb6 100644
--- a/lib/crates/fabro-devcontainer/src/features.rs
+++ b/lib/crates/fabro-devcontainer/src/features.rs
@@ -564,9 +564,12 @@ pub(crate) async fn resolve_features(
             .as_nanos()
     );
     let tmp_dir = std::env::temp_dir().join(unique_id);
-    fs::create_dir_all(&tmp_dir)
-        .await
-        .map_err(|e| DevcontainerError::Feature(format!("failed to create temp dir: {e}")))?;
+    fs::create_dir_all(&tmp_dir).await.map_err(|e| {
+        DevcontainerError::Feature(format!(
+            "failed to create temp dir {}: {e}",
+            tmp_dir.display()
+        ))
+    })?;
 
     // Collect feature IDs in a stable order
     let mut feature_ids: Vec<String> = features.keys().cloned().collect();
diff --git a/lib/crates/fabro-interview/src/recording.rs b/lib/crates/fabro-interview/src/recording.rs
index 8c7ef8f2b..9d803916a 100644
--- a/lib/crates/fabro-interview/src/recording.rs
+++ b/lib/crates/fabro-interview/src/recording.rs
@@ -53,7 +53,12 @@ impl RecordingInterviewer {
     /// Returns an error if serialization or file writing fails.
     pub fn save_to_file(&self, path: &Path) -> std::io::Result<()> {
         let json = self.to_json()?;
-        std::fs::write(path, json)?;
+        std::fs::write(path, json).map_err(|err| {
+            std::io::Error::new(
+                err.kind(),
+                format!("write interview recording {}: {err}", path.display()),
+            )
+        })?;
         Ok(())
     }
 
@@ -62,7 +67,12 @@ impl RecordingInterviewer {
     /// # Errors
     /// Returns an error if file reading or deserialization fails.
     pub fn load_from_file(path: &Path) -> std::io::Result<Vec<(Question, Answer)>> {
-        let json = std::fs::read_to_string(path)?;
+        let json = std::fs::read_to_string(path).map_err(|err| {
+            std::io::Error::new(
+                err.kind(),
+                format!("read interview recording {}: {err}", path.display()),
+            )
+        })?;
         Self::from_json(&json)
     }
 }
diff --git a/lib/crates/fabro-llm/src/providers/common.rs b/lib/crates/fabro-llm/src/providers/common.rs
index 2a227476e..6a3cae449 100644
--- a/lib/crates/fabro-llm/src/providers/common.rs
+++ b/lib/crates/fabro-llm/src/providers/common.rs
@@ -100,7 +100,9 @@ pub fn load_file_as_base64(path: &str) -> Result<(String, String), std::io::Erro
             format!("{home}/{rest}")
         },
     );
-    let data = std::fs::read(&expanded)?;
+    let data = std::fs::read(&expanded).map_err(|err| {
+        std::io::Error::new(err.kind(), format!("read attachment {expanded}: {err}"))
+    })?;
     let mime = mime_from_extension(&expanded).to_string();
     let b64 = BASE64_STANDARD.encode(&data);
     Ok((b64, mime))
diff --git a/lib/crates/fabro-server/src/serve.rs b/lib/crates/fabro-server/src/serve.rs
index 728b22e32..6f87f03e1 100644
--- a/lib/crates/fabro-server/src/serve.rs
+++ b/lib/crates/fabro-server/src/serve.rs
@@ -157,7 +157,8 @@ fn build_local_object_store_with_preference(
         return Ok(Arc::new(InMemory::new()));
     }
 
-    std::fs::create_dir_all(store_path)?;
+    std::fs::create_dir_all(store_path)
+        .with_context(|| format!("creating object store directory {}", store_path.display()))?;
     Ok(Arc::new(LocalFileSystem::new_with_prefix(store_path)?))
 }
 
@@ -318,7 +319,8 @@ where
     let bind_request =
         resolve_bind_request_from_settings(&effective_settings, args.bind.as_deref())?;
     let shared_settings = Arc::new(RwLock::new(effective_settings));
-    std::fs::create_dir_all(&data_dir)?;
+    std::fs::create_dir_all(&data_dir)
+        .with_context(|| format!("creating data directory {}", data_dir.display()))?;
     let (auth_mode, max_concurrent_runs) = {
         let auth_mode = resolve_auth_mode_with_lookup(&resolved_server_settings, |name| {
             server_secrets.get(name)
@@ -499,7 +501,9 @@ where
 
     #[cfg(debug_assertions)]
     let mut watch_web_child = if watch_web {
-        let web_dir = std::env::current_dir()?.join("apps/fabro-web");
+        let web_dir = std::env::current_dir()
+            .context("reading current directory for --watch-web")?
+            .join("apps/fabro-web");
         info!(dir = %web_dir.display(), "Starting bun run dev (--watch-web)");
         #[expect(
             clippy::disallowed_methods,
@@ -508,7 +512,8 @@ where
         let child = std::process::Command::new("bun")
             .args(["run", "dev"])
             .current_dir(&web_dir)
-            .spawn()?;
+            .spawn()
+            .with_context(|| format!("spawning `bun run dev` in {}", web_dir.display()))?;
         Some(child)
     } else {
         None
@@ -577,10 +582,12 @@ async fn bind_listener(requested: &BindRequest) -> anyhow::Result<BoundServerLis
     match requested {
         BindRequest::Unix(path) => {
             if path.exists() {
-                std::fs::remove_file(path)?;
+                std::fs::remove_file(path)
+                    .with_context(|| format!("removing stale unix socket {}", path.display()))?;
             }
 
-            let listener = UnixListener::bind(path)?;
+            let listener = UnixListener::bind(path)
+                .with_context(|| format!("binding unix socket {}", path.display()))?;
             Ok(BoundServerListener {
                 listener: BoundListener::Unix(listener),
                 bind: Bind::Unix(path.clone()),
diff --git a/lib/crates/fabro-server/src/server.rs b/lib/crates/fabro-server/src/server.rs
index 307977817..16b84edc5 100644
--- a/lib/crates/fabro-server/src/server.rs
+++ b/lib/crates/fabro-server/src/server.rs
@@ -6,6 +6,7 @@ use std::sync::atomic::{AtomicBool, Ordering};
 use std::sync::{Arc, LazyLock, Mutex, RwLock};
 use std::time::{Duration, Instant};
 
+use anyhow::Context as _;
 use axum::body::Body;
 #[cfg(test)]
 use axum::body::to_bytes;
@@ -3363,8 +3364,8 @@ fn worker_command(
     mode: RunExecutionMode,
     run_dir: &std::path::Path,
 ) -> anyhow::Result<Command> {
-    let exe =
-        std::env::var_os("CARGO_BIN_EXE_fabro").map_or(std::env::current_exe()?, PathBuf::from);
+    let current_exe = std::env::current_exe().context("reading current executable path")?;
+    let exe = std::env::var_os("CARGO_BIN_EXE_fabro").map_or(current_exe, PathBuf::from);
     let storage_dir = state.server_storage_dir();
     let server_target = current_server_target(&storage_dir)?;
     let artifact_upload_token = state
@@ -4257,7 +4258,7 @@ async fn execute_run_subprocess(state: Arc<AppState>, run_id: RunId) {
     ));
 
     let mut child = match worker_command(state.as_ref(), run_id, execution_mode, &run_dir)
-        .and_then(|mut cmd| cmd.spawn().map_err(anyhow::Error::from))
+        .and_then(|mut cmd| cmd.spawn().context("spawning run worker process"))
     {
         Ok(child) => child,
         Err(err) => {
diff --git a/lib/crates/fabro-telemetry/src/panic.rs b/lib/crates/fabro-telemetry/src/panic.rs
index e6f575411..e2fa7ac08 100644
--- a/lib/crates/fabro-telemetry/src/panic.rs
+++ b/lib/crates/fabro-telemetry/src/panic.rs
@@ -1,6 +1,7 @@
 use std::panic::PanicHookInfo;
 use std::path::Path;
 
+use anyhow::Context as _;
 use sentry::integrations::backtrace;
 use sentry::protocol::{Context, Event, Exception, Mechanism, OsContext, Values};
 
@@ -116,7 +117,8 @@ fn spawn_panic_sender(event: &Event<'static>) {
 pub fn capture(path: &Path) -> anyhow::Result<()> {
     let dsn = SENTRY_DSN.ok_or_else(|| anyhow::anyhow!("SENTRY_DSN not set at compile time"))?;
 
-    let json = std::fs::read(path)?;
+    let json =
+        std::fs::read(path).with_context(|| format!("read panic payload {}", path.display()))?;
     let event: Event<'static> = serde_json::from_slice(&json)?;
 
     let guard = sentry::init((dsn, sentry::ClientOptions::default()));
diff --git a/lib/crates/fabro-telemetry/src/sender.rs b/lib/crates/fabro-telemetry/src/sender.rs
index b4161a3cb..0c2b531a5 100644
--- a/lib/crates/fabro-telemetry/src/sender.rs
+++ b/lib/crates/fabro-telemetry/src/sender.rs
@@ -1,5 +1,6 @@
 use std::path::Path;
 
+use anyhow::Context;
 use base64::Engine;
 use base64::engine::general_purpose::STANDARD;
 use uuid::Uuid;
@@ -122,7 +123,8 @@ pub async fn upload(path: &Path) -> anyhow::Result<()> {
     let write_key = SEGMENT_WRITE_KEY
         .ok_or_else(|| anyhow::anyhow!("SEGMENT_WRITE_KEY not set at compile time"))?;
 
-    let content = std::fs::read_to_string(path)?;
+    let content = std::fs::read_to_string(path)
+        .with_context(|| format!("read telemetry batch {}", path.display()))?;
     let Some(payload) = build_segment_batch(&content) else {
         return Ok(());
     };
diff --git a/lib/crates/fabro-util/src/dev_token.rs b/lib/crates/fabro-util/src/dev_token.rs
index 6013d2331..238a86f59 100644
--- a/lib/crates/fabro-util/src/dev_token.rs
+++ b/lib/crates/fabro-util/src/dev_token.rs
@@ -2,7 +2,7 @@ use std::fs;
 use std::io::Write as _;
 use std::path::Path;
 
-use anyhow::{Result, anyhow};
+use anyhow::{Context, Result, anyhow};
 use rand::TryRngCore;
 use rand::rngs::OsRng;
 
@@ -52,7 +52,10 @@ pub fn load_or_create_dev_token(path: &Path) -> Result<String> {
             return Err(anyhow!("invalid dev token format in {}", path.display()));
         }
         Err(err) if err.kind() == std::io::ErrorKind::NotFound => {}
-        Err(err) => return Err(err.into()),
+        Err(err) => {
+            return Err(anyhow::Error::from(err))
+                .with_context(|| format!("read dev token {}", path.display()));
+        }
     }
 
     let token = generate_dev_token();
@@ -70,7 +73,8 @@ pub fn write_dev_token(path: &Path, token: &str) -> Result<()> {
 
 fn atomic_write_private(path: &Path, contents: &str) -> Result<()> {
     if let Some(parent) = path.parent() {
-        fs::create_dir_all(parent)?;
+        fs::create_dir_all(parent)
+            .with_context(|| format!("create directory {}", parent.display()))?;
     }
 
     let temp_path = path.with_file_name(format!(
@@ -81,7 +85,8 @@ fn atomic_write_private(path: &Path, contents: &str) -> Result<()> {
         rand::random::<u64>()
     ));
     write_private_file(&temp_path, contents)?;
-    fs::rename(&temp_path, path)?;
+    fs::rename(&temp_path, path)
+        .with_context(|| format!("rename {} to {}", temp_path.display(), path.display()))?;
     Ok(())
 }
 
@@ -96,13 +101,17 @@ fn write_private_file(path: &Path, contents: &str) -> Result<()> {
             .create(true)
             .truncate(true)
             .mode(0o600)
-            .open(path)?
+            .open(path)
+            .with_context(|| format!("open {} for writing", path.display()))?
     };
 
     #[cfg(not(unix))]
-    let mut file = std::fs::File::create(path)?;
+    let mut file =
+        std::fs::File::create(path).with_context(|| format!("create {}", path.display()))?;
 
-    file.write_all(contents.as_bytes())?;
-    file.sync_all()?;
+    file.write_all(contents.as_bytes())
+        .with_context(|| format!("write {}", path.display()))?;
+    file.sync_all()
+        .with_context(|| format!("sync {}", path.display()))?;
     Ok(())
 }
diff --git a/lib/crates/fabro-vault/src/lib.rs b/lib/crates/fabro-vault/src/lib.rs
index 676249333..57e777581 100644
--- a/lib/crates/fabro-vault/src/lib.rs
+++ b/lib/crates/fabro-vault/src/lib.rs
@@ -1,6 +1,6 @@
 use std::collections::HashMap;
-use std::fmt;
 use std::path::{Component, Path, PathBuf};
+use std::{fmt, io};
 
 #[derive(Debug, Clone, Copy, PartialEq, Eq, Default, serde::Serialize, serde::Deserialize)]
 #[serde(rename_all = "snake_case")]
@@ -77,7 +77,7 @@ impl Vault {
         let entries = match std::fs::read_to_string(&path) {
             Ok(contents) => serde_json::from_str(&contents)?,
             Err(err) if err.kind() == std::io::ErrorKind::NotFound => HashMap::new(),
-            Err(err) => return Err(err.into()),
+            Err(err) => return Err(io_context("read vault", &path, &err).into()),
         };
 
         Ok(Self { path, entries })
@@ -231,7 +231,8 @@ impl Vault {
             .path
             .parent()
             .map_or_else(|| PathBuf::from("."), Path::to_path_buf);
-        std::fs::create_dir_all(&parent)?;
+        std::fs::create_dir_all(&parent)
+            .map_err(|err| io_context("create vault directory", &parent, &err))?;
 
         let file_name = self
             .path
@@ -240,18 +241,32 @@ impl Vault {
             .unwrap_or("secrets.json");
         let tmp_path = parent.join(format!(".{file_name}.tmp-{}", ulid::Ulid::new()));
         let json = serde_json::to_vec_pretty(&self.entries)?;
-        std::fs::write(&tmp_path, json)?;
+        std::fs::write(&tmp_path, json)
+            .map_err(|err| io_context("write vault temp file", &tmp_path, &err))?;
         set_private_permissions(&tmp_path)?;
-        std::fs::rename(&tmp_path, &self.path)?;
+        std::fs::rename(&tmp_path, &self.path).map_err(|err| {
+            io_context(
+                &format!("rename vault temp file to {}", self.path.display()),
+                &tmp_path,
+                &err,
+            )
+        })?;
         Ok(())
     }
 }
 
+/// Wrap an `io::Error` with a human-readable verb and path so downstream
+/// reporting shows which operation failed on which file.
+fn io_context(op: &str, path: &Path, source: &io::Error) -> io::Error {
+    io::Error::new(source.kind(), format!("{op} {}: {source}", path.display()))
+}
+
 #[cfg(unix)]
 fn set_private_permissions(path: &Path) -> Result<(), Error> {
     use std::os::unix::fs::PermissionsExt;
 
-    std::fs::set_permissions(path, std::fs::Permissions::from_mode(0o600))?;
+    std::fs::set_permissions(path, std::fs::Permissions::from_mode(0o600))
+        .map_err(|err| io_context("set permissions on", path, &err))?;
     Ok(())
 }
 
diff --git a/lib/crates/fabro-workflow/src/artifact.rs b/lib/crates/fabro-workflow/src/artifact.rs
index 3347c717e..b9757ca94 100644
--- a/lib/crates/fabro-workflow/src/artifact.rs
+++ b/lib/crates/fabro-workflow/src/artifact.rs
@@ -282,9 +282,16 @@ async fn materialize_blob_ref(
         let path = local_materialized_blob_path(run_dir, blob_id);
         if !path.exists() {
             if let Some(parent) = path.parent() {
-                std::fs::create_dir_all(parent)?;
+                std::fs::create_dir_all(parent).map_err(|err| {
+                    Error::Io(format!(
+                        "creating artifact blob directory {}: {err}",
+                        parent.display()
+                    ))
+                })?;
             }
-            std::fs::write(&path, &bytes)?;
+            std::fs::write(&path, &bytes).map_err(|err| {
+                Error::Io(format!("writing artifact blob {}: {err}", path.display()))
+            })?;
         }
         return Ok(format!("{ARTIFACT_POINTER_PREFIX}{}", path.display()));
     }
diff --git a/lib/crates/fabro-workflow/src/operations/start.rs b/lib/crates/fabro-workflow/src/operations/start.rs
index ba6a91751..2f4b29c5a 100644
--- a/lib/crates/fabro-workflow/src/operations/start.rs
+++ b/lib/crates/fabro-workflow/src/operations/start.rs
@@ -107,7 +107,12 @@ pub struct Started {
 /// Start a fresh workflow run. Errors if a checkpoint already exists (use
 /// `resume()` instead).
 pub async fn start(run_dir: &Path, services: StartServices) -> Result<Started, Error> {
-    std::fs::create_dir_all(run_dir).map_err(|err| Error::Io(err.to_string()))?;
+    std::fs::create_dir_all(run_dir).map_err(|err| {
+        Error::Io(format!(
+            "creating run directory {}: {err}",
+            run_dir.display()
+        ))
+    })?;
     let state = services
         .run_store
         .state()
diff --git a/lib/crates/fabro-workflow/src/pipeline/persist.rs b/lib/crates/fabro-workflow/src/pipeline/persist.rs
index 523abf0b0..c1e935b49 100644
--- a/lib/crates/fabro-workflow/src/pipeline/persist.rs
+++ b/lib/crates/fabro-workflow/src/pipeline/persist.rs
@@ -13,7 +13,12 @@ pub(crate) fn persist(
     let (graph, source, diagnostics) = validated.into_parts();
     options.run_record.graph = graph.clone();
 
-    std::fs::create_dir_all(&options.run_dir)?;
+    std::fs::create_dir_all(&options.run_dir).map_err(|err| {
+        Error::Io(format!(
+            "creating run directory {}: {err}",
+            options.run_dir.display()
+        ))
+    })?;
 
     Ok(Persisted::new(
         graph,
diff --git a/lib/crates/fabro-workflow/src/run_lookup.rs b/lib/crates/fabro-workflow/src/run_lookup.rs
index 24036067a..56b3c4ff6 100644
--- a/lib/crates/fabro-workflow/src/run_lookup.rs
+++ b/lib/crates/fabro-workflow/src/run_lookup.rs
@@ -148,7 +148,10 @@ fn scan_orphan_runs(base: &Path) -> Result<Vec<RunInfo>> {
     let entries = match std::fs::read_dir(base) {
         Ok(entries) => entries,
         Err(err) if err.kind() == std::io::ErrorKind::NotFound => return Ok(Vec::new()),
-        Err(err) => return Err(err.into()),
+        Err(err) => {
+            return Err(anyhow::Error::new(err)
+                .context(format!("reading orphan runs directory {}", base.display())));
+        }
     };
 
     let mut runs = Vec::new();