diff --git a/crates/goose/src/providers/formats/databricks.rs b/crates/goose/src/providers/formats/databricks.rs
index 7918c75004..38d84111b9 100644
--- a/crates/goose/src/providers/formats/databricks.rs
+++ b/crates/goose/src/providers/formats/databricks.rs
@@ -124,6 +124,8 @@ fn format_messages(messages: &[Message], image_format: &ImageFormat) -> Vec<Data
         let mut content_array = Vec::new();
         let mut has_tool_calls = false;
         let mut has_multiple_content = false;
+        // Deferred so all tool-role messages stay consecutive (required by Claude via Databricks).
+        let mut pending_image_messages: Vec<DatabricksMessage> = Vec::new();
 
         for content in &message.content {
             match content {
@@ -190,7 +192,13 @@ fn format_messages(messages: &[Message], image_format: &ImageFormat) -> Vec<Data
                     }
                 }
                 MessageContent::ToolResponse(response) => {
-                    result.extend(format_tool_response(response, image_format));
+                    for msg in format_tool_response(response, image_format) {
+                        if msg.role == "user" {
+                            pending_image_messages.push(msg);
+                        } else {
+                            result.push(msg);
+                        }
+                    }
                 }
                 MessageContent::Image(image) => {
                     content_array.push(convert_image(image, image_format));
@@ -212,6 +220,8 @@ fn format_messages(messages: &[Message], image_format: &ImageFormat) -> Vec<Data
             }
         }
 
+        result.extend(pending_image_messages);
+
         if !content_array.is_empty() {
             converted.content = if content_array.len() == 1
                 && !has_multiple_content
@@ -1683,4 +1693,70 @@ mod tests {
 
         Ok(())
     }
+
+    #[test]
+    fn test_parallel_tool_responses_with_images_are_consecutive() -> anyhow::Result<()> {
+        // Regression: #7449 — parallel tool calls with images must keep tool messages consecutive.
+        let messages = vec![
+            Message::assistant()
+                .with_tool_request("id1", Ok(CallToolRequestParams::new("tool_a")))
+                .with_tool_request("id2", Ok(CallToolRequestParams::new("tool_b"))),
+            Message::user()
+                .with_tool_response(
+                    "id1",
+                    Ok(CallToolResult::success(vec![Content::image(
+                        "base64data1".to_string(),
+                        "image/png".to_string(),
+                    )])),
+                )
+                .with_tool_response(
+                    "id2",
+                    Ok(CallToolResult::success(vec![Content::image(
+                        "base64data2".to_string(),
+                        "image/png".to_string(),
+                    )])),
+                ),
+        ];
+
+        let as_value =
+            serde_json::to_value(format_messages(&messages, &ImageFormat::OpenAi)).unwrap();
+        let spec = as_value.as_array().unwrap();
+        let roles: Vec<&str> = spec.iter().map(|m| m["role"].as_str().unwrap()).collect();
+
+        // Without the fix this was ["assistant", "tool", "user", "tool", "user"].
+        assert_eq!(roles, vec!["assistant", "tool", "tool", "user", "user"]);
+
+        Ok(())
+    }
+
+    #[test]
+    fn test_mixed_tool_responses_image_and_text_ordering() -> anyhow::Result<()> {
+        // Mixed case: only one tool response has an image.
+        let messages = vec![
+            Message::assistant()
+                .with_tool_request("id1", Ok(CallToolRequestParams::new("tool_a")))
+                .with_tool_request("id2", Ok(CallToolRequestParams::new("tool_b"))),
+            Message::user()
+                .with_tool_response(
+                    "id1",
+                    Ok(CallToolResult::success(vec![Content::text("text result")])),
+                )
+                .with_tool_response(
+                    "id2",
+                    Ok(CallToolResult::success(vec![Content::image(
+                        "base64data".to_string(),
+                        "image/png".to_string(),
+                    )])),
+                ),
+        ];
+
+        let as_value =
+            serde_json::to_value(format_messages(&messages, &ImageFormat::OpenAi)).unwrap();
+        let spec = as_value.as_array().unwrap();
+        let roles: Vec<&str> = spec.iter().map(|m| m["role"].as_str().unwrap()).collect();
+
+        assert_eq!(roles, vec!["assistant", "tool", "tool", "user"]);
+
+        Ok(())
+    }
 }