diff --git a/codex-rs/core/src/codex.rs b/codex-rs/core/src/codex.rs
index e3c5de5762..4b4daf8f19 100644
--- a/codex-rs/core/src/codex.rs
+++ b/codex-rs/core/src/codex.rs
@@ -102,6 +102,7 @@ use crate::protocol::TurnDiffEvent;
 use crate::protocol::WarningEvent;
 use crate::rollout::RolloutRecorder;
 use crate::rollout::RolloutRecorderParams;
+use crate::rollout::map_session_init_error;
 use crate::shell;
 use crate::state::ActiveTurn;
 use crate::state::SessionServices;
@@ -206,7 +207,7 @@ impl Codex {
         .await
         .map_err(|e| {
             error!("Failed to create session: {e:#}");
-            CodexErr::InternalAgentDied
+            map_session_init_error(&e, &config.codex_home)
         })?;
         let conversation_id = session.conversation_id;
 
@@ -508,7 +509,7 @@ impl Session {
 
         let rollout_recorder = rollout_recorder.map_err(|e| {
             error!("failed to initialize rollout recorder: {e:#}");
-            anyhow::anyhow!("failed to initialize rollout recorder: {e:#}")
+            anyhow::Error::from(e)
         })?;
         let rollout_path = rollout_recorder.rollout_path.clone();
 
diff --git a/codex-rs/core/src/rollout/error.rs b/codex-rs/core/src/rollout/error.rs
new file mode 100644
index 0000000000..e924dd2d28
--- /dev/null
+++ b/codex-rs/core/src/rollout/error.rs
@@ -0,0 +1,49 @@
+use std::io::ErrorKind;
+use std::path::Path;
+
+use crate::error::CodexErr;
+use crate::rollout::SESSIONS_SUBDIR;
+
+pub(crate) fn map_session_init_error(err: &anyhow::Error, codex_home: &Path) -> CodexErr {
+    if let Some(mapped) = err
+        .chain()
+        .filter_map(|cause| cause.downcast_ref::<std::io::Error>())
+        .find_map(|io_err| map_rollout_io_error(io_err, codex_home))
+    {
+        return mapped;
+    }
+
+    CodexErr::Fatal(format!("Failed to initialize session: {err:#}"))
+}
+
+fn map_rollout_io_error(io_err: &std::io::Error, codex_home: &Path) -> Option<CodexErr> {
+    let sessions_dir = codex_home.join(SESSIONS_SUBDIR);
+    let hint = match io_err.kind() {
+        ErrorKind::PermissionDenied => format!(
+            "Codex cannot access session files at {} (permission denied). If sessions were created using sudo, fix ownership: sudo chown -R $(whoami) {}",
+            sessions_dir.display(),
+            codex_home.display()
+        ),
+        ErrorKind::NotFound => format!(
+            "Session storage missing at {}. Create the directory or choose a different Codex home.",
+            sessions_dir.display()
+        ),
+        ErrorKind::AlreadyExists => format!(
+            "Session storage path {} is blocked by an existing file. Remove or rename it so Codex can create sessions.",
+            sessions_dir.display()
+        ),
+        ErrorKind::InvalidData | ErrorKind::InvalidInput => format!(
+            "Session data under {} looks corrupt or unreadable. Clearing the sessions directory may help (this will remove saved conversations).",
+            sessions_dir.display()
+        ),
+        ErrorKind::IsADirectory | ErrorKind::NotADirectory => format!(
+            "Session storage path {} has an unexpected type. Ensure it is a directory Codex can use for session files.",
+            sessions_dir.display()
+        ),
+        _ => return None,
+    };
+
+    Some(CodexErr::Fatal(format!(
+        "{hint} (underlying error: {io_err})"
+    )))
+}
diff --git a/codex-rs/core/src/rollout/mod.rs b/codex-rs/core/src/rollout/mod.rs
index 23410bd4d0..540d204be3 100644
--- a/codex-rs/core/src/rollout/mod.rs
+++ b/codex-rs/core/src/rollout/mod.rs
@@ -7,11 +7,13 @@ pub const ARCHIVED_SESSIONS_SUBDIR: &str = "archived_sessions";
 pub const INTERACTIVE_SESSION_SOURCES: &[SessionSource] =
     &[SessionSource::Cli, SessionSource::VSCode];
 
+pub(crate) mod error;
 pub mod list;
 pub(crate) mod policy;
 pub mod recorder;
 
 pub use codex_protocol::protocol::SessionMeta;
+pub(crate) use error::map_session_init_error;
 pub use list::find_conversation_path_by_id_str;
 pub use recorder::RolloutRecorder;
 pub use recorder::RolloutRecorderParams;