diff --git a/src/client/bedrock.rs b/src/client/bedrock.rs
index 0988694..1a94f5d 100644
--- a/src/client/bedrock.rs
+++ b/src/client/bedrock.rs
@@ -457,10 +457,15 @@ fn build_chat_completions_body(
                                 }
                             }));
                         }
-                        vec![
-                            json!({ "role": "assistant", "content": assistant_parts }),
-                            json!({ "role": "user", "content": user_parts }),
-                        ]
+                        // Empty tool_results (reachable via deserialized sessions) must not emit an empty pair.
+                        if assistant_parts.is_empty() {
+                            vec![]
+                        } else {
+                            vec![
+                                json!({ "role": "assistant", "content": assistant_parts }),
+                                json!({ "role": "user", "content": user_parts }),
+                            ]
+                        }
                     } else {
                         // One pair per round: Claude can reuse tool_use IDs across API calls.
                         // A round boundary is detected by the presence of round text, but
@@ -872,7 +877,7 @@ mod tests {
         }
     }
 
-    fn build_body(tool_results: Vec<ToolResult>) -> Value {
+    fn build_body_with(tool_results: Vec<ToolResult>, text: &str, sequence: bool) -> Value {
         let data = ChatCompletionsData {
             messages: vec![
                 Message::new(MessageRole::User, MessageContent::Text("hello".to_string())),
@@ -880,8 +885,8 @@ mod tests {
                     MessageRole::Assistant,
                     MessageContent::ToolCalls(MessageContentToolCalls {
                         tool_results,
-                        text: String::new(),
-                        sequence: true,
+                        text: text.to_string(),
+                        sequence,
                     }),
                 ),
             ],
@@ -894,6 +899,10 @@ mod tests {
         build_chat_completions_body(data, &Model::new("bedrock", "test"), false).unwrap()
     }
 
+    fn build_body(tool_results: Vec<ToolResult>) -> Value {
+        build_body_with(tool_results, "", true)
+    }
+
     fn tool_result_content_block(output: Value) -> Value {
         let body = build_body(vec![tool_result(output)]);
         body["messages"][2]["content"][0]["toolResult"]["content"][0].clone()
@@ -1063,6 +1072,44 @@ mod tests {
         assert_unique_tool_use_ids_per_message(&body);
     }
 
+    #[test]
+    fn non_sequence_emits_assistant_user_pair() {
+        let body = build_body_with(
+            vec![
+                sequence_tool_result("toolu_A", None),
+                sequence_tool_result("toolu_B", None),
+            ],
+            "",
+            false,
+        );
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 3, "body: {body}");
+        assert_eq!(messages[1]["role"], "assistant");
+        assert_eq!(messages[1]["content"].as_array().unwrap().len(), 2);
+        assert_eq!(messages[2]["role"], "user");
+        assert_eq!(messages[2]["content"].as_array().unwrap().len(), 2);
+    }
+
+    #[test]
+    fn non_sequence_empty_tool_results_emits_no_messages() {
+        let body = build_body_with(vec![], "leftover text", false);
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 1, "body: {body}");
+    }
+
+    #[test]
+    fn sequence_empty_tool_results_emits_no_messages() {
+        let body = build_body_with(vec![], "leftover text", true);
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 1, "body: {body}");
+    }
+
     #[test]
     fn test_bedrock_tool_result_object_uses_json_block() {
         assert_eq!(
diff --git a/src/client/claude.rs b/src/client/claude.rs
index 019b379..9b2b051 100644
--- a/src/client/claude.rs
+++ b/src/client/claude.rs
@@ -381,10 +381,15 @@ pub fn claude_build_chat_completions_body(
                                 "content": tool_result.output.to_string(),
                             }));
                         }
-                        vec![
-                            json!({ "role": "assistant", "content": assistant_parts }),
-                            json!({ "role": "user", "content": user_parts }),
-                        ]
+                        // Empty tool_results (reachable via deserialized sessions) must not emit an empty pair.
+                        if assistant_parts.is_empty() {
+                            vec![]
+                        } else {
+                            vec![
+                                json!({ "role": "assistant", "content": assistant_parts }),
+                                json!({ "role": "user", "content": user_parts }),
+                            ]
+                        }
                     } else {
                         // One pair per round: Claude can reuse tool_use IDs across API calls.
                         // A round boundary is detected by the presence of round text, but
@@ -638,7 +643,12 @@ mod tests {
         }
     }
 
-    fn build_body(tool_results: Vec<ToolResult>, prompt_cache: bool) -> Value {
+    fn build_body_with(
+        tool_results: Vec<ToolResult>,
+        text: &str,
+        sequence: bool,
+        prompt_cache: bool,
+    ) -> Value {
         let data = ChatCompletionsData {
             messages: vec![
                 Message::new(MessageRole::User, MessageContent::Text("hello".to_string())),
@@ -646,8 +656,8 @@ mod tests {
                     MessageRole::Assistant,
                     MessageContent::ToolCalls(MessageContentToolCalls {
                         tool_results,
-                        text: String::new(),
-                        sequence: true,
+                        text: text.to_string(),
+                        sequence,
                     }),
                 ),
             ],
@@ -661,6 +671,10 @@ mod tests {
             .unwrap()
     }
 
+    fn build_body(tool_results: Vec<ToolResult>, prompt_cache: bool) -> Value {
+        build_body_with(tool_results, "", true, prompt_cache)
+    }
+
     fn multi_turn_data(functions: Option<Vec<FunctionDeclaration>>) -> ChatCompletionsData {
         ChatCompletionsData {
             messages: vec![
@@ -766,6 +780,42 @@ mod tests {
         assert_unique_tool_use_ids_per_message(&body);
     }
 
+    #[test]
+    fn non_sequence_emits_assistant_user_pair() {
+        let body = build_body_with(
+            vec![tool_result("toolu_A", None), tool_result("toolu_B", None)],
+            "",
+            false,
+            false,
+        );
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 3, "body: {body}");
+        assert_eq!(messages[1]["role"], "assistant");
+        assert_eq!(messages[1]["content"].as_array().unwrap().len(), 2);
+        assert_eq!(messages[2]["role"], "user");
+        assert_eq!(messages[2]["content"].as_array().unwrap().len(), 2);
+    }
+
+    #[test]
+    fn non_sequence_empty_tool_results_emits_no_messages() {
+        let body = build_body_with(vec![], "leftover text", false, false);
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 1, "body: {body}");
+    }
+
+    #[test]
+    fn sequence_empty_tool_results_emits_no_messages() {
+        let body = build_body_with(vec![], "leftover text", true, false);
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 1, "body: {body}");
+    }
+
     #[test]
     fn prompt_cache_places_breakpoints() {
         let functions = vec![function_declaration("a"), function_declaration("b")];
diff --git a/src/client/openai.rs b/src/client/openai.rs
index 6633be3..2c47d87 100644
--- a/src/client/openai.rs
+++ b/src/client/openai.rs
@@ -373,7 +373,10 @@ pub fn openai_build_chat_completions_body(data: ChatCompletionsData, model: &Mod
                     text,
                     sequence,
                 }) => {
-                    if !sequence {
+                    // Empty tool_results (reachable via deserialized sessions) must not emit empty tool_calls.
+                    if tool_results.is_empty() {
+                        vec![]
+                    } else if !sequence {
                         let tool_calls: Vec<_> = tool_results
                             .iter()
                             .map(|tool_result| {
@@ -745,3 +748,48 @@ pub async fn openai_responses_streaming(
 
     sse_stream(builder, handle).await
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    fn build_body(sequence: bool) -> Value {
+        let data = ChatCompletionsData {
+            messages: vec![
+                Message::new(MessageRole::User, MessageContent::Text("hello".to_string())),
+                Message::new(
+                    MessageRole::Assistant,
+                    MessageContent::ToolCalls(MessageContentToolCalls {
+                        tool_results: vec![],
+                        text: "leftover text".to_string(),
+                        sequence,
+                    }),
+                ),
+            ],
+            temperature: None,
+            top_p: None,
+            reasoning_effort: None,
+            functions: None,
+            stream: false,
+        };
+        openai_build_chat_completions_body(data, &Model::new("openai", "gpt-test"))
+    }
+
+    #[test]
+    fn non_sequence_empty_tool_results_emits_no_messages() {
+        let body = build_body(false);
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 1, "body: {body}");
+    }
+
+    #[test]
+    fn sequence_empty_tool_results_emits_no_messages() {
+        let body = build_body(true);
+
+        let messages = body["messages"].as_array().unwrap();
+
+        assert_eq!(messages.len(), 1, "body: {body}");
+    }
+}
diff --git a/src/client/vertexai.rs b/src/client/vertexai.rs
index 3f1f6f5..d9f3fed 100644
--- a/src/client/vertexai.rs
+++ b/src/client/vertexai.rs
@@ -412,10 +412,15 @@ pub fn gemini_build_chat_completions_body(
                                 }
                             })
                         }).collect();
-                        vec![
-                            json!({ "role": "model", "parts": model_parts }),
-                            json!({ "role": "function", "parts": function_parts }),
-                        ]
+                        // Empty tool_results (reachable via deserialized sessions) must not emit an empty pair.
+                        if function_parts.is_empty() {
+                            vec![]
+                        } else {
+                            vec![
+                                json!({ "role": "model", "parts": model_parts }),
+                                json!({ "role": "function", "parts": function_parts }),
+                            ]
+                        }
                     }
                 }
         })
@@ -579,3 +584,37 @@ fn strip_model_version(name: &str) -> &str {
         None => name,
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn gemini_empty_tool_results_emits_no_messages() {
+        let data = ChatCompletionsData {
+            messages: vec![
+                Message::new(MessageRole::User, MessageContent::Text("hello".to_string())),
+                Message::new(
+                    MessageRole::Assistant,
+                    MessageContent::ToolCalls(MessageContentToolCalls {
+                        tool_results: vec![],
+                        text: "leftover text".to_string(),
+                        sequence: false,
+                    }),
+                ),
+            ],
+            temperature: None,
+            top_p: None,
+            reasoning_effort: None,
+            functions: None,
+            stream: false,
+        };
+
+        let body = gemini_build_chat_completions_body(data, &Model::new("vertexai", "gemini-test"))
+            .unwrap();
+
+        let contents = body["contents"].as_array().unwrap();
+
+        assert_eq!(contents.len(), 1, "body: {body}");
+    }
+}