diff --git a/anthropic.go b/anthropic.go
index 784cc32..b2982dc 100644
--- a/anthropic.go
+++ b/anthropic.go
@@ -71,6 +71,11 @@ func (a anthropic) requestToAnthropicRequest(req Request) anth.MessagesRequest {
 			}
 
 			for _, img := range msg.Images {
+				// anthropic doesn't allow the assistant to send images, so we need to say it's from the user
+				if m.Role == anth.RoleAssistant {
+					m.Role = anth.RoleUser
+				}
+
 				if img.Base64 != "" {
 					m.Content = append(m.Content, anth.NewImageMessageContent(
 						anth.NewMessageContentSource(