From d5849bdf52c05b522729319091666a52dc26601c Mon Sep 17 00:00:00 2001
From: Abdellatif Anaflous <62770500+hktitof@users.noreply.github.com>
Date: Sun, 30 Aug 2026 02:09:53 +0100
Subject: [PATCH] fix(attachment): detect heic/heif mime type from filename
 extension (#6246)

Signed-off-by: Abdel <hktitof@gmail.com>
---
 server/router/api/v1/attachment_mime_test.go | 54 ++++++++++++++++++++
 server/router/api/v1/attachment_service.go   | 34 ++++++++++--
 2 files changed, 83 insertions(+), 5 deletions(-)
 create mode 100644 server/router/api/v1/attachment_mime_test.go

diff --git a/server/router/api/v1/attachment_mime_test.go b/server/router/api/v1/attachment_mime_test.go
new file mode 100644
index 00000000..58a5abfc
--- /dev/null
+++ b/server/router/api/v1/attachment_mime_test.go
@@ -0,0 +1,54 @@
+package v1
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestDetectAttachmentMimeType(t *testing.T) {
+	tests := []struct {
+		name     string
+		filename string
+		content  []byte
+		want     string
+	}{
+		{
+			name:     "heic image via extension fallback",
+			filename: "photo.heic",
+			want:     "image/heic",
+		},
+		{
+			name:     "heif image via extension fallback",
+			filename: "photo.heif",
+			want:     "image/heif",
+		},
+		{
+			name:     "uppercase HEIC extension",
+			filename: "PHOTO.HEIC",
+			want:     "image/heic",
+		},
+		{
+			name:     "regular image by builtin extension",
+			filename: "image.png",
+			want:     "image/png",
+		},
+		{
+			name:     "unknown extension falls back to content sniffing",
+			filename: "photo.xyz",
+			content:  []byte{0x89, 0x50, 0x4e, 0x47, 0x0d, 0x0a, 0x1a, 0x0a},
+			want:     "image/png",
+		},
+		{
+			name:     "no extension and no sniffable content",
+			filename: "attachment",
+			want:     "text/plain; charset=utf-8",
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := detectAttachmentMimeType(tt.filename, tt.content)
+			require.Equal(t, tt.want, got)
+		})
+	}
+}
diff --git a/server/router/api/v1/attachment_service.go b/server/router/api/v1/attachment_service.go
index 699ea912..07967b36 100644
--- a/server/router/api/v1/attachment_service.go
+++ b/server/router/api/v1/attachment_service.go
@@ -8,6 +8,7 @@ import (
 	"mime"
 	"net/http"
 	"path/filepath"
+	"strings"
 	"time"
 
 	"google.golang.org/grpc/codes"
@@ -43,6 +44,33 @@ var exifCapableImageTypes = map[string]bool{
 	"image/heif": true,
 }
 
+// extensionMimeTypeFallbacks maps image extensions that Go's builtin MIME
+// table does not cover. HEIC/HEIF files are the common case: browsers report
+// an empty MIME type for them, Go's builtin table omits the extension, and
+// http.DetectContentType cannot sniff the ISO BMFF container, so without
+// this fallback these uploads are stored as "application/octet-stream" on
+// minimal runtimes that ship no system MIME database (e.g. the Alpine image).
+var extensionMimeTypeFallbacks = map[string]string{
+	".heic": "image/heic",
+	".heif": "image/heif",
+}
+
+// detectAttachmentMimeType resolves the MIME type for an uploaded file that
+// arrived without a client-supplied type. It prefers the filename extension
+// (including the curated fallback above, which keeps the result identical on
+// machines with and without a system MIME database), then sniffs the content
+// as a last resort.
+func detectAttachmentMimeType(filename string, content []byte) string {
+	ext := strings.ToLower(filepath.Ext(filename))
+	if mimeType, ok := extensionMimeTypeFallbacks[ext]; ok {
+		return mimeType
+	}
+	if mimeType := mime.TypeByExtension(ext); mimeType != "" {
+		return mimeType
+	}
+	return http.DetectContentType(content)
+}
+
 func (s *APIV1Service) CreateAttachment(ctx context.Context, request *v1pb.CreateAttachmentRequest) (*v1pb.Attachment, error) {
 	user, err := s.fetchCurrentUser(ctx)
 	if err != nil {
@@ -64,11 +92,7 @@ func (s *APIV1Service) CreateAttachment(ctx context.Context, request *v1pb.Creat
 	}
 	normalizedMimeType := request.Attachment.Type
 	if normalizedMimeType == "" {
-		ext := filepath.Ext(request.Attachment.Filename)
-		mimeType := mime.TypeByExtension(ext)
-		if mimeType == "" {
-			mimeType = http.DetectContentType(request.Attachment.Content)
-		}
+		mimeType := detectAttachmentMimeType(request.Attachment.Filename, request.Attachment.Content)
 		if normalizedType, ok := normalizeMimeType(mimeType); ok {
 			normalizedMimeType = normalizedType
 		}