diff --git a/cliff.toml b/cliff.toml
deleted file mode 100644
index f31e1bd89c..0000000000
--- a/cliff.toml
+++ /dev/null
@@ -1,46 +0,0 @@
-# https://git-cliff.org/docs/configuration
-
-[changelog]
-header = """
-# Changelog
-
-You can install any of these versions: `npm install -g @openai/codex@<version>`
-"""
-
-body = """
-{% if version -%}
-## [{{ version | trim_start_matches(pat="v") }}] - {{ timestamp | date(format="%Y-%m-%d") }}
-{%- else %}
-## [unreleased]
-{% endif %}
-
-{%- for group, commits in commits | group_by(attribute="group") %}
-### {{ group | striptags | trim }}
-
-{% for commit in commits %}- {% if commit.scope %}*({{ commit.scope }})* {% endif %}{% if commit.breaking %}[**breaking**] {% endif %}{{ commit.message | upper_first }}
-{% endfor %}
-
-{%- endfor -%}
-"""
-
-footer = """
-<!-- generated - do not edit -->
-"""
-
-trim = true
-postprocessors = []
-
-[git]
-conventional_commits = true
-
-commit_parsers = [
-  { message = "^feat", group = "<!-- 0 -->🚀 Features" },
-  { message = "^fix",  group = "<!-- 1 -->🪲 Bug Fixes" },
-  { message = "^bump", group = "<!-- 6 -->🛳️ Release" },
-  # Fallback – skip anything that didn't match the above rules.
-  { message = ".*",  group = "<!-- 10 -->💼 Other" },
-]
-
-filter_unconventional = false
-sort_commits = "oldest"
-topo_order = false
\ No newline at end of file
diff --git a/codex-rs/Cargo.lock b/codex-rs/Cargo.lock
index 3561550db5..6ac51d403f 100644
--- a/codex-rs/Cargo.lock
+++ b/codex-rs/Cargo.lock
@@ -3077,6 +3077,7 @@ dependencies = [
  "anyhow",
  "codex-login",
  "codex-protocol",
+ "mime_guess",
  "pretty_assertions",
  "sentry",
  "tracing",
diff --git a/codex-rs/feedback/Cargo.toml b/codex-rs/feedback/Cargo.toml
index 032f0398be..dd89ddb76b 100644
--- a/codex-rs/feedback/Cargo.toml
+++ b/codex-rs/feedback/Cargo.toml
@@ -11,6 +11,7 @@ workspace = true
 anyhow = { workspace = true }
 codex-login = { workspace = true }
 codex-protocol = { workspace = true }
+mime_guess = { workspace = true }
 sentry = { version = "0.46" }
 tracing = { workspace = true }
 tracing-subscriber = { workspace = true }
diff --git a/codex-rs/feedback/src/lib.rs b/codex-rs/feedback/src/lib.rs
index 7c27d2b3b0..cd97349c48 100644
--- a/codex-rs/feedback/src/lib.rs
+++ b/codex-rs/feedback/src/lib.rs
@@ -4,6 +4,7 @@ use std::collections::btree_map::Entry;
 use std::fs;
 use std::io::Write;
 use std::io::{self};
+use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
 use std::sync::Mutex;
@@ -593,10 +594,22 @@ impl FeedbackSnapshot {
                         .map(|s| s.to_string_lossy().to_string())
                         .unwrap_or_else(|| "extra-log.log".to_string())
                 });
+            let content_type = match Path::new(&filename)
+                .extension()
+                .and_then(|extension| extension.to_str())
+            {
+                Some(extension) if extension.eq_ignore_ascii_case("jsonl") => {
+                    "text/plain".to_string()
+                }
+                _ => mime_guess::from_path(&filename)
+                    .first_or_octet_stream()
+                    .essence_str()
+                    .to_string(),
+            };
             attachments.push(Attachment {
                 buffer: data,
                 filename,
-                content_type: Some("text/plain".to_string()),
+                content_type: Some(content_type),
                 ty: None,
             });
         }
@@ -774,6 +787,10 @@ mod tests {
             b"Connectivity diagnostics\n\n- Proxy environment variables are set and may affect connectivity.\n  - HTTPS_PROXY = https://example.com:443".to_vec()
         );
         assert_eq!(attachments_with_diagnostics[3].buffer, b"rollout".to_vec());
+        assert_eq!(
+            attachments_with_diagnostics[3].content_type.as_deref(),
+            Some("text/plain")
+        );
         assert_eq!(
             OsStr::new(attachments_with_diagnostics[3].filename.as_str()),
             OsStr::new(extra_filename.as_str())
@@ -794,6 +811,62 @@ mod tests {
         fs::remove_file(extra_path).expect("extra attachment should be removed");
     }
 
+    #[test]
+    fn path_backed_attachments_use_binary_content_types() {
+        let suffix = ThreadId::new();
+        let gzip_filename = format!("codex-desktop-app-logs-{suffix}.tar.gz");
+        let unknown_filename = format!("codex-feedback-extra-{suffix}.binunknown");
+        let gzip_path = std::env::temp_dir().join(&gzip_filename);
+        let unknown_path = std::env::temp_dir().join(&unknown_filename);
+        let gzip_bytes = b"\x1f\x8b\x08\x00\xff";
+        let unknown_bytes = b"\x00\x9f\x92\x96";
+        fs::write(&gzip_path, gzip_bytes).expect("gzip attachment should be written");
+        fs::write(&unknown_path, unknown_bytes).expect("unknown attachment should be written");
+
+        let attachments = CodexFeedback::new()
+            .snapshot(/*session_id*/ None)
+            .feedback_attachments(
+                /*include_logs*/ false,
+                &[],
+                &[
+                    FeedbackAttachmentPath {
+                        path: gzip_path.clone(),
+                        attachment_filename_override: None,
+                    },
+                    FeedbackAttachmentPath {
+                        path: unknown_path.clone(),
+                        attachment_filename_override: None,
+                    },
+                ],
+                /*logs_override*/ None,
+            );
+
+        fs::remove_file(gzip_path).expect("gzip attachment should be removed");
+        fs::remove_file(unknown_path).expect("unknown attachment should be removed");
+        assert_eq!(
+            attachments
+                .iter()
+                .map(|attachment| (
+                    attachment.filename.as_str(),
+                    attachment.content_type.as_deref(),
+                    attachment.buffer.as_slice(),
+                ))
+                .collect::<Vec<_>>(),
+            vec![
+                (
+                    gzip_filename.as_str(),
+                    Some("application/gzip"),
+                    gzip_bytes.as_slice(),
+                ),
+                (
+                    unknown_filename.as_str(),
+                    Some("application/octet-stream"),
+                    unknown_bytes.as_slice(),
+                ),
+            ]
+        );
+    }
+
     #[test]
     fn upload_tags_include_client_tags_and_preserve_reserved_fields() {
         let mut tags = BTreeMap::new();