diff --git a/codex-rs/core/src/context_manager/history.rs b/codex-rs/core/src/context_manager/history.rs
index 0fb1cd3bd2..cd5fc70394 100644
--- a/codex-rs/core/src/context_manager/history.rs
+++ b/codex-rs/core/src/context_manager/history.rs
@@ -9,6 +9,8 @@ use crate::event_mapping::is_contextual_user_message_content;
 use crate::session::turn_context::TurnContext;
 use base64::Engine;
 use base64::engine::general_purpose::STANDARD as BASE64_STANDARD;
+use codex_context_fragments::set_annotated_content;
+use codex_context_fragments::to_annotated_content;
 use codex_extension_api::ConversationHistorySnapshot;
 use codex_history::CodexHarnessMetadata;
 use codex_history::ResponseItemEnvelope;
@@ -345,17 +347,19 @@ impl ContextManager {
         {
             retained_items.retain_mut(|item| {
                 if item.turn_id() == Some(first_turn_id)
-                    && let ResponseItem::Message { role, content, .. } = &mut item.item
-                    && role == "developer"
+                    && matches!(&item.item, ResponseItem::Message { role, .. } if role == "developer")
                 {
+                    let Some(mut content) = to_annotated_content(&mut item.item) else {
+                        return false;
+                    };
                     content.retain(|content| {
                         !matches!(
-                            content,
+                            content.content(),
                             ContentItem::InputText { text }
                                 if ModelSwitchInstructions::matches_text(text)
                         )
                     });
-                    !content.is_empty()
+                    !content.is_empty() && set_annotated_content(&mut item.item, content).is_some()
                 } else {
                     true
                 }
diff --git a/codex-rs/core/src/context_manager/history_tests.rs b/codex-rs/core/src/context_manager/history_tests.rs
index a1088310bc..5a0c6e2602 100644
--- a/codex-rs/core/src/context_manager/history_tests.rs
+++ b/codex-rs/core/src/context_manager/history_tests.rs
@@ -11,6 +11,7 @@ use codex_protocol::AgentPath;
 use codex_protocol::ResponseItemId;
 use codex_protocol::models::BaseInstructions;
 use codex_protocol::models::ContentItem;
+use codex_protocol::models::ContentItemKind;
 use codex_protocol::models::DEFAULT_IMAGE_DETAIL;
 use codex_protocol::models::FunctionCallOutputBody;
 use codex_protocol::models::FunctionCallOutputContentItem;
@@ -1255,6 +1256,67 @@ fn drop_last_n_user_turns_trims_context_updates_above_rolled_back_turn() {
     );
 }
 
+#[test]
+fn drop_last_n_user_turns_preserves_annotations_for_surviving_developer_fragments() {
+    let turn_id = "rolled-back-turn";
+    let model_switch = ModelSwitchInstructions::new("switched model instructions").render();
+    let developer_message = ResponseItem::Message {
+        id: None,
+        role: "developer".to_string(),
+        content: vec![
+            ContentItem::InputText {
+                text: "persistent developer instructions".to_string(),
+            },
+            ContentItem::InputText { text: model_switch },
+            ContentItem::InputText {
+                text: "persistent environment instructions".to_string(),
+            },
+        ],
+        phase: None,
+        internal_chat_message_metadata_passthrough: Some(InternalChatMessageMetadataPassthrough {
+            turn_id: Some(turn_id.to_string()),
+            content_item_kinds: Some(vec![
+                ContentItemKind("generic.developer_instructions".to_string()),
+                ContentItemKind("model_switch.instructions".to_string()),
+                ContentItemKind("environments.instructions".to_string()),
+            ]),
+            ..Default::default()
+        }),
+    };
+    let mut user_message = user_input_text_msg("turn to roll back");
+    user_message.set_turn_id_if_missing(turn_id);
+    let mut history = create_history_with_items(vec![developer_message, user_message]);
+
+    history.drop_last_n_user_turns(/*num_turns*/ 1);
+
+    assert_eq!(
+        raw_items(&history),
+        vec![ResponseItem::Message {
+            id: None,
+            role: "developer".to_string(),
+            content: vec![
+                ContentItem::InputText {
+                    text: "persistent developer instructions".to_string(),
+                },
+                ContentItem::InputText {
+                    text: "persistent environment instructions".to_string(),
+                },
+            ],
+            phase: None,
+            internal_chat_message_metadata_passthrough: Some(
+                InternalChatMessageMetadataPassthrough {
+                    turn_id: Some(turn_id.to_string()),
+                    content_item_kinds: Some(vec![
+                        ContentItemKind("generic.developer_instructions".to_string()),
+                        ContentItemKind("environments.instructions".to_string()),
+                    ]),
+                    ..Default::default()
+                },
+            ),
+        }],
+    );
+}
+
 #[test]
 fn drop_last_n_user_turns_trims_saved_prefix_update_above_rolled_back_turn() {
     let items = vec![
diff --git a/codex-rs/core/tests/suite/model_switching.rs b/codex-rs/core/tests/suite/model_switching.rs
index 0eaa0748ae..4bd09d11ae 100644
--- a/codex-rs/core/tests/suite/model_switching.rs
+++ b/codex-rs/core/tests/suite/model_switching.rs
@@ -345,6 +345,20 @@ async fn rollback_first_turn_model_change_removes_its_instructions(
 
     let request = &response_mock.requests()[1];
     assert_eq!(request.body_json()["model"], followup_model);
+    let misaligned_messages = request
+        .inputs_of_type("message")
+        .into_iter()
+        .filter(|message| {
+            message["internal_chat_message_metadata_passthrough"]["content_item_kinds"]
+                .as_array()
+                .is_some_and(|kinds| {
+                    message["content"]
+                        .as_array()
+                        .is_none_or(|content| content.len() != kinds.len())
+                })
+        })
+        .collect::<Vec<_>>();
+    assert_eq!(misaligned_messages, Vec::<serde_json::Value>::new());
     let model_switch_count = request
         .message_input_texts("developer")
         .iter()