From 014278357aa43a05af9b151718bb272c63f98c84 Mon Sep 17 00:00:00 2001
From: Eric Jacksch <securityguy@users.noreply.github.com>
Date: Thu, 12 Mar 2026 19:22:34 -0400
Subject: [PATCH] fix(openai_compat): omit empty content when tool_calls
 present

Some providers (via OpenRouter) reject assistant messages with
"content": "" alongside tool_calls. The OpenAI spec permits content to
be absent when tool_calls is set. Switch openaiMessage.Content from
string to *string with omitempty and introduce msgContent() to return
nil when content is empty and tool calls are present.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
---
 pkg/providers/openai_compat/provider.go      | 78 ++++++++++++++++++++
 pkg/providers/openai_compat/provider_test.go | 45 +++++++++++
 2 files changed, 123 insertions(+)

diff --git a/pkg/providers/openai_compat/provider.go b/pkg/providers/openai_compat/provider.go
index fb2abaa5c..f0d07c0f0 100644
--- a/pkg/providers/openai_compat/provider.go
+++ b/pkg/providers/openai_compat/provider.go
@@ -175,6 +175,84 @@ func (p *Provider) Chat(
 	return common.ReadAndParseResponse(resp, p.apiBase)
 }
 
+// openaiMessage is the wire-format message for OpenAI-compatible APIs.
+// It mirrors protocoltypes.Message but omits SystemParts, which is an
+// internal field that would be unknown to third-party endpoints.
+type openaiMessage struct {
+	Role             string     `json:"role"`
+	Content          *string    `json:"content,omitempty"`
+	ReasoningContent string     `json:"reasoning_content,omitempty"`
+	ToolCalls        []ToolCall `json:"tool_calls,omitempty"`
+	ToolCallID       string     `json:"tool_call_id,omitempty"`
+}
+
+// msgContent returns the content pointer for an outbound message.
+// When content is empty and tool_calls are present, nil is returned so the
+// field is omitted entirely. The OpenAI spec allows content to be absent (or
+// null) when tool_calls is set, and some strict providers reject "" in that
+// position, causing intermittent failures.
+func msgContent(content string, toolCalls []ToolCall) *string {
+	if content == "" && len(toolCalls) > 0 {
+		return nil
+	}
+	return &content
+}
+
+// serializeMessages converts internal Message structs to the OpenAI wire format.
+// - Strips SystemParts (unknown to third-party endpoints)
+// - Converts messages with Media to multipart content format (text + image_url parts)
+// - Preserves ToolCallID, ToolCalls, and ReasoningContent for all messages
+func serializeMessages(messages []Message) []any {
+	out := make([]any, 0, len(messages))
+	for _, m := range messages {
+		if len(m.Media) == 0 {
+			out = append(out, openaiMessage{
+				Role:             m.Role,
+				Content:          msgContent(m.Content, m.ToolCalls),
+				ReasoningContent: m.ReasoningContent,
+				ToolCalls:        m.ToolCalls,
+				ToolCallID:       m.ToolCallID,
+			})
+			continue
+		}
+
+		// Multipart content format for messages with media
+		parts := make([]map[string]any, 0, 1+len(m.Media))
+		if m.Content != "" {
+			parts = append(parts, map[string]any{
+				"type": "text",
+				"text": m.Content,
+			})
+		}
+		for _, mediaURL := range m.Media {
+			if strings.HasPrefix(mediaURL, "data:image/") {
+				parts = append(parts, map[string]any{
+					"type": "image_url",
+					"image_url": map[string]any{
+						"url": mediaURL,
+					},
+				})
+			}
+		}
+
+		msg := map[string]any{
+			"role":    m.Role,
+			"content": parts,
+		}
+		if m.ToolCallID != "" {
+			msg["tool_call_id"] = m.ToolCallID
+		}
+		if len(m.ToolCalls) > 0 {
+			msg["tool_calls"] = m.ToolCalls
+		}
+		if m.ReasoningContent != "" {
+			msg["reasoning_content"] = m.ReasoningContent
+		}
+		out = append(out, msg)
+	}
+	return out
+}
+
 func normalizeModel(model, apiBase string) string {
 	before, after, ok := strings.Cut(model, "/")
 	if !ok {
diff --git a/pkg/providers/openai_compat/provider_test.go b/pkg/providers/openai_compat/provider_test.go
index ed9747f9d..27f1fedda 100644
--- a/pkg/providers/openai_compat/provider_test.go
+++ b/pkg/providers/openai_compat/provider_test.go
@@ -824,6 +824,51 @@ func TestSupportsPromptCacheKey(t *testing.T) {
 	}
 }
 
+func TestSerializeMessages_OmitsContentWhenEmptyAndToolCallsPresent(t *testing.T) {
+	messages := []protocoltypes.Message{
+		{
+			Role:    "assistant",
+			Content: "",
+			ToolCalls: []protocoltypes.ToolCall{
+				{ID: "call_1", Type: "function", Function: &protocoltypes.FunctionCall{Name: "fn", Arguments: "{}"}},
+			},
+		},
+	}
+	result := serializeMessages(messages)
+
+	data, _ := json.Marshal(result)
+	var msgs []map[string]any
+	json.Unmarshal(data, &msgs)
+
+	if _, ok := msgs[0]["content"]; ok {
+		t.Fatalf("content should be omitted when empty and tool_calls present, got %v", msgs[0]["content"])
+	}
+	if msgs[0]["tool_calls"] == nil {
+		t.Fatal("tool_calls should be present")
+	}
+}
+
+func TestSerializeMessages_IncludesContentWhenNonEmptyWithToolCalls(t *testing.T) {
+	messages := []protocoltypes.Message{
+		{
+			Role:    "assistant",
+			Content: "thinking...",
+			ToolCalls: []protocoltypes.ToolCall{
+				{ID: "call_1", Type: "function", Function: &protocoltypes.FunctionCall{Name: "fn", Arguments: "{}"}},
+			},
+		},
+	}
+	result := serializeMessages(messages)
+
+	data, _ := json.Marshal(result)
+	var msgs []map[string]any
+	json.Unmarshal(data, &msgs)
+
+	if msgs[0]["content"] != "thinking..." {
+		t.Fatalf("content should be preserved when non-empty, got %v", msgs[0]["content"])
+	}
+}
+
 func TestSerializeMessages_StripsSystemParts(t *testing.T) {
 	messages := []protocoltypes.Message{
 		{