diff --git a/llm/cli.py b/llm/cli.py
index 33e14f09..454e56ca 100644
--- a/llm/cli.py
+++ b/llm/cli.py
@@ -76,6 +76,7 @@ def convert(self, value, param, ctx):
         path = pathlib.Path(value)
         if not path.exists():
             self.fail(f"File {value} does not exist", param, ctx)
+        path = path.resolve()
         # Try to guess type
         mimetype = puremagic.from_file(str(path), mime=True)
         return Attachment(mimetype, str(path), None, None)
@@ -94,6 +95,7 @@ def attachment_types_callback(ctx, param, values):
             path = pathlib.Path(value)
             if not path.exists():
                 raise click.BadParameter(f"File {value} does not exist")
+            path = path.resolve()
             attachment = Attachment(mimetype, str(path), None, None)
         collected.append(attachment)
     return collected
diff --git a/llm/migrations.py b/llm/migrations.py
index 008ae976..91da6429 100644
--- a/llm/migrations.py
+++ b/llm/migrations.py
@@ -201,3 +201,29 @@ def m010_create_new_log_tables(db):
 @migration
 def m011_fts_for_responses(db):
     db["responses"].enable_fts(["prompt", "response"], create_triggers=True)
+
+
+@migration
+def m012_attachments_tables(db):
+    db["attachments"].create(
+        {
+            "id": str,
+            "type": str,
+            "path": str,
+            "url": str,
+            "content": bytes,
+        },
+        pk="id",
+    )
+    db["prompt_attachments"].create(
+        {
+            "response_id": str,
+            "attachment_id": str,
+            "order": int,
+        },
+        foreign_keys=(
+            ("response_id", "responses", "id"),
+            ("attachment_id", "attachments", "id"),
+        ),
+        pk=("response_id", "attachment_id"),
+    )
diff --git a/llm/models.py b/llm/models.py
index 77bdb8e9..3b7d4dad 100644
--- a/llm/models.py
+++ b/llm/models.py
@@ -2,6 +2,7 @@
 from dataclasses import dataclass, field
 import datetime
 from .errors import NeedsKeyException
+import hashlib
 import httpx
 from itertools import islice
 import puremagic
@@ -23,6 +24,17 @@ class Attachment:
     url: Optional[str] = None
     content: Optional[bytes] = None
 
+    def hash_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()
+
     def resolve_type(self):
         if self.type:
             return self.type
@@ -178,8 +190,9 @@ def log_to_db(self, db):
             },
             ignore=True,
         )
+        response_id = str(ULID()).lower()
         response = {
-            "id": str(ULID()).lower(),
+            "id": response_id,
             "model": self.model.model_id,
             "prompt": self.prompt.prompt,
             "system": self.prompt.system,
@@ -196,6 +209,26 @@ def log_to_db(self, db):
             "datetime_utc": self.datetime_utc(),
         }
         db["responses"].insert(response)
+        # Persist any attachments - loop through with index
+        for index, attachment in enumerate(self.prompt.attachments):
+            attachment_id = attachment.hash_id()
+            db["attachments"].insert(
+                {
+                    "id": attachment_id,
+                    "type": attachment.resolve_type(),
+                    "path": attachment.path,
+                    "url": attachment.url,
+                    "content": attachment.content,
+                },
+                replace=True,
+            )
+            db["prompt_attachments"].insert(
+                {
+                    "response_id": response_id,
+                    "attachment_id": attachment_id,
+                    "order": index,
+                },
+            )
 
     @classmethod
     def fake(