diff --git a/llm/cli.py b/llm/cli.py
index 454e56c..53087ad 100644
--- a/llm/cli.py
+++ b/llm/cli.py
@@ -62,7 +62,7 @@ class AttachmentType(click.ParamType):
                 mimetype = puremagic.from_string(content, mime=True)
             except puremagic.PureError:
                 raise click.BadParameter("Could not determine mimetype of stdin")
-            return Attachment(mimetype, None, None, content)
+            return Attachment(type=mimetype, path=None, url=None, content=content)
         if "://" in value:
             # Confirm URL exists and try to guess type
             try:
@@ -79,7 +79,7 @@ class AttachmentType(click.ParamType):
         path = path.resolve()
         # Try to guess type
         mimetype = puremagic.from_file(str(path), mime=True)
-        return Attachment(mimetype, str(path), None, None)
+        return Attachment(type=mimetype, path=str(path), url=None, content=None)
 
 
 def attachment_types_callback(ctx, param, values):
@@ -552,7 +552,7 @@ def load_conversation(conversation_id: Optional[str]) -> Optional[Conversation]:
     for response in db["responses"].rows_where(
         "conversation_id = ?", [conversation_id]
     ):
-        conversation.responses.append(Response.from_row(response))
+        conversation.responses.append(Response.from_row(db, response))
     return conversation
 
 
diff --git a/llm/default_plugins/openai_models.py b/llm/default_plugins/openai_models.py
index 913e754..651d37f 100644
--- a/llm/default_plugins/openai_models.py
+++ b/llm/default_plugins/openai_models.py
@@ -312,23 +312,39 @@ class Chat(Model):
                         {"role": "system", "content": prev_response.prompt.system}
                     )
                     current_system = prev_response.prompt.system
-                messages.append(
-                    {"role": "user", "content": prev_response.prompt.prompt}
-                )
+                if prev_response.attachments:
+                    attachment_message = [
+                        {"type": "text", "text": prev_response.prompt.prompt}
+                    ]
+                    for attachment in prev_response.attachments:
+                        url = attachment.url
+                        if not url:
+                            base64_image = attachment.base64_content()
+                            url = f"data:{attachment.resolve_type()};base64,{base64_image}"
+                        attachment_message.append(
+                            {"type": "image_url", "image_url": {"url": url}}
+                        )
+                    messages.append({"role": "user", "content": attachment_message})
+                else:
+                    messages.append(
+                        {"role": "user", "content": prev_response.prompt.prompt}
+                    )
                 messages.append({"role": "assistant", "content": prev_response.text()})
         if prompt.system and prompt.system != current_system:
             messages.append({"role": "system", "content": prompt.system})
         if not prompt.attachments:
             messages.append({"role": "user", "content": prompt.prompt})
         else:
-            vision_message = [{"type": "text", "text": prompt.prompt}]
+            attachment_message = [{"type": "text", "text": prompt.prompt}]
             for attachment in prompt.attachments:
                 url = attachment.url
                 if not url:
                     base64_image = attachment.base64_content()
                     url = f"data:{attachment.resolve_type()};base64,{base64_image}"
-                vision_message.append({"type": "image_url", "image_url": {"url": url}})
-            messages.append({"role": "user", "content": vision_message})
+                attachment_message.append(
+                    {"type": "image_url", "image_url": {"url": url}}
+                )
+            messages.append({"role": "user", "content": attachment_message})
 
         response._prompt_json = {"messages": messages}
         kwargs = self.build_kwargs(prompt)
diff --git a/llm/models.py b/llm/models.py
index 3b7d4da..fc58a07 100644
--- a/llm/models.py
+++ b/llm/models.py
@@ -23,17 +23,20 @@ class Attachment:
     path: Optional[str] = None
     url: Optional[str] = None
     content: Optional[bytes] = None
+    _id: Optional[str] = None
 
-    def hash_id(self):
+    def id(self):
         # Hash of the binary content, or of '{"url": "https://..."}' for URL attachments
-        if self.content:
-            return hashlib.sha256(self.content).hexdigest()
-        elif self.path:
-            return hashlib.sha256(open(self.path, "rb").read()).hexdigest()
-        else:
-            return hashlib.sha256(
-                json.dumps({"url": self.url}).encode("utf-8")
-            ).hexdigest()
+        if self._id is None:
+            if self.content:
+                self._id = hashlib.sha256(self.content).hexdigest()
+            elif self.path:
+                self._id = hashlib.sha256(open(self.path, "rb").read()).hexdigest()
+            else:
+                self._id = hashlib.sha256(
+                    json.dumps({"url": self.url}).encode("utf-8")
+                ).hexdigest()
+        return self._id
 
     def resolve_type(self):
         if self.type:
@@ -58,6 +61,16 @@ class Attachment:
                 content = response.content
         return base64.b64encode(content).decode("utf-8")
 
+    @classmethod
+    def from_row(cls, row):
+        return cls(
+            _id=row["id"],
+            type=row["type"],
+            path=row["path"],
+            url=row["url"],
+            content=row["content"],
+        )
+
 
 @dataclass
 class Prompt:
@@ -211,7 +224,7 @@ class Response(ABC):
         db["responses"].insert(response)
         # Persist any attachments - loop through with index
         for index, attachment in enumerate(self.prompt.attachments):
-            attachment_id = attachment.hash_id()
+            attachment_id = attachment.id()
             db["attachments"].insert(
                 {
                     "id": attachment_id,
@@ -255,7 +268,7 @@ class Response(ABC):
         return response_obj
 
     @classmethod
-    def from_row(cls, row):
+    def from_row(cls, db, row):
         from llm import get_model
 
         model = get_model(row["model"])
@@ -276,6 +289,19 @@ class Response(ABC):
         response.response_json = json.loads(row["response_json"] or "null")
         response._done = True
         response._chunks = [row["response"]]
+        # Attachments
+        response.attachments = [
+            Attachment.from_row(arow)
+            for arow in db.query(
+                """
+                select attachments.* from attachments
+                join prompt_attachments on attachments.id = prompt_attachments.attachment_id
+                where prompt_attachments.response_id = ?
+                order by prompt_attachments."order"
+            """,
+                [row["id"]],
+            )
+        ]
         return response
 
     def __repr__(self):