diff --git a/coderd/exp_chats_test.go b/coderd/exp_chats_test.go
index 4f47e23c6a..23cb181ed9 100644
--- a/coderd/exp_chats_test.go
+++ b/coderd/exp_chats_test.go
@@ -7309,10 +7309,7 @@ func TestChatMessageWithFiles(t *testing.T) {
 
 		// Only MaxChatFileIDs files should actually be linked.
 		// With SQL-level batch rejection, ALL files are rejected
-		// when the result would exceed the cap. Since we're
-		// sending MaxChatFileIDs+1 files, the deduped count is
-		// 21 > 20, so 0 rows are affected and all files are
-		// unlinked.
+		// when the result would exceed the cap.
 		chatResult, err := client.GetChat(ctx, chat.ID)
 		require.NoError(t, err)
 		require.Empty(t, chatResult.Files, "no files should be linked when batch exceeds cap")
diff --git a/coderd/x/chatd/chattool/attachfile_test.go b/coderd/x/chatd/chattool/attachfile_test.go
index 4230b42459..52bb41bb37 100644
--- a/coderd/x/chatd/chattool/attachfile_test.go
+++ b/coderd/x/chatd/chattool/attachfile_test.go
@@ -257,14 +257,14 @@ func TestAttachFile(t *testing.T) {
 			Return(io.NopCloser(strings.NewReader("build succeeded\n")), "text/plain", nil)
 
 		tool := newAttachFileTool(t, mockConn, func(_ context.Context, _ string, _ string, _ []byte) (chattool.AttachmentMetadata, error) {
-			return chattool.AttachmentMetadata{}, xerrors.New("chat already has the maximum of 20 linked files")
+			return chattool.AttachmentMetadata{}, xerrors.New("ETOOMANYFILES")
 		})
 		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
 			ID: "call-cap", Name: "attach_file", Input: `{"path":"/home/coder/build.log"}`,
 		})
 		require.NoError(t, err)
 		assert.True(t, resp.IsError)
-		assert.Contains(t, resp.Content, "chat already has the maximum of 20 linked files")
+		assert.Contains(t, resp.Content, "ETOOMANYFILES")
 	})
 }
 
diff --git a/coderd/x/chatd/chattool/computeruse_test.go b/coderd/x/chatd/chattool/computeruse_test.go
index 5138003345..ec6ba045db 100644
--- a/coderd/x/chatd/chattool/computeruse_test.go
+++ b/coderd/x/chatd/chattool/computeruse_test.go
@@ -273,7 +273,7 @@ func TestComputerUseTool_Run_Screenshot_StoreErrorFallsBackToImage(t *testing.T)
 	tool := chattool.NewComputerUseTool(chattool.ComputerUseProviderAnthropic, geometry.DeclaredWidth, geometry.DeclaredHeight, func(_ context.Context) (workspacesdk.AgentConn, error) {
 		return mockConn, nil
 	}, func(_ context.Context, _ string, _ string, _ []byte) (chattool.AttachmentMetadata, error) {
-		return chattool.AttachmentMetadata{}, xerrors.New("chat already has the maximum of 20 linked files")
+		return chattool.AttachmentMetadata{}, xerrors.New("ETOOMANYFILES")
 	}, quartz.NewReal(), slogtest.Make(t, nil))
 
 	resp, err := tool.Run(context.Background(), fantasy.ToolCall{
@@ -652,7 +652,7 @@ func TestComputerUseTool_Run_OpenAI_FinalScreenshotStoreErrorFallsBackToImage(t
 	recordDesktopActions(t, mockConn, geometry, 1, screenshotPNG)
 
 	tool := newOpenAIComputerUseTool(t, geometry, mockConn, func(_ context.Context, _ string, _ string, _ []byte) (chattool.AttachmentMetadata, error) {
-		return chattool.AttachmentMetadata{}, xerrors.New("chat already has the maximum of 20 linked files")
+		return chattool.AttachmentMetadata{}, xerrors.New("ETOOMANYFILES")
 	}, quartz.NewReal())
 
 	resp, err := tool.Run(context.Background(), openAIComputerUseCall(`{
diff --git a/coderd/x/chatd/store_chat_attachment_test.go b/coderd/x/chatd/store_chat_attachment_test.go
index 0bb4eb29bb..70325bd945 100644
--- a/coderd/x/chatd/store_chat_attachment_test.go
+++ b/coderd/x/chatd/store_chat_attachment_test.go
@@ -2,6 +2,7 @@ package chatd //nolint:testpackage
 
 import (
 	"context"
+	"fmt"
 	"testing"
 
 	"github.com/google/uuid"
@@ -216,7 +217,7 @@ func TestStoreChatAttachment_StrictCapError(t *testing.T) {
 	}).Return(int32(1), nil)
 
 	attachment, err := server.storeChatAttachment(context.Background(), chatSnapshot, "build.log", "build.log", []byte("build output"))
-	require.ErrorContains(t, err, "chat already has the maximum of 20 linked files")
+	require.ErrorContains(t, err, fmt.Sprintf("chat already has the maximum of %d linked files", codersdk.MaxChatFileIDs))
 	require.Equal(t, chattool.AttachmentMetadata{}, attachment)
 }
 
diff --git a/codersdk/chats.go b/codersdk/chats.go
index 4c8706c42c..562bc0014d 100644
--- a/codersdk/chats.go
+++ b/codersdk/chats.go
@@ -31,7 +31,7 @@ const ChatCompactionThresholdKeyPrefix = "chat_compaction_threshold_pct:"
 // associated with a single chat. This limit prevents unbounded
 // growth in the chat_file_links table. It is easier to raise
 // this limit than to lower it.
-const MaxChatFileIDs = 20
+const MaxChatFileIDs = 50
 
 // MaxChatFileSizeBytes is the upload-endpoint cap for chat
 // attachments.
diff --git a/site/src/api/typesGenerated.ts b/site/src/api/typesGenerated.ts
index 75e4bb2b10..4ce4e9945b 100644
--- a/site/src/api/typesGenerated.ts
+++ b/site/src/api/typesGenerated.ts
@@ -5126,7 +5126,7 @@ export interface MatchedProvisioners {
  * growth in the chat_file_links table. It is easier to raise
  * this limit than to lower it.
  */
-export const MaxChatFileIDs = 20;
+export const MaxChatFileIDs = 50;
 
 // From codersdk/chats.go
 /**