diff --git a/CHDataManagement/Generator/ImageGenerator.swift b/CHDataManagement/Generator/ImageGenerator.swift
index e3b335e..a758c7a 100644
--- a/CHDataManagement/Generator/ImageGenerator.swift
+++ b/CHDataManagement/Generator/ImageGenerator.swift
@@ -19,7 +19,7 @@ final class ImageGenerator {
         settings.paths.imagesOutputFolderPath
     }
 
-    private func needsToGenerate(_ version: ImageVersion) -> Bool {
+    func needsToGenerate(_ version: ImageVersion) -> Bool {
         if version.wasPreviouslyGenerated {
             return !exists(version) 
         }
@@ -44,10 +44,6 @@ final class ImageGenerator {
     // MARK: Image operations
 
     func generate(version: ImageVersion) -> Bool {
-        guard needsToGenerate(version) else {
-            return true
-        }
-
         if version.type == .avif {
             if version.image.type == .gif {
                 // Skip GIFs, since they can't be converted by avifenc
diff --git a/CHDataManagement/Model/Content+Generation.swift b/CHDataManagement/Model/Content+Generation.swift
index 134e2c6..b1d4a22 100644
--- a/CHDataManagement/Model/Content+Generation.swift
+++ b/CHDataManagement/Model/Content+Generation.swift
@@ -72,19 +72,48 @@ extension Content {
 
     private func generateRequiredImages() {
         let images = results.imagesToGenerate.sorted()
+
         let count = images.count
         var completed = 0
+
+        func didFinishOneImage() {
+            completed += 1
+            status("Generating required images: \(completed) / \(count)")
+        }
+
+        // Finish existing images
+        var newImagesToGenerate: [ImageVersion] = []
+        var avifImagesToGenerate: [ImageVersion] = []
         for image in images {
             guard shouldGenerateWebsite else { return }
-            defer {
-                completed += 1
-                status("Generating required images: \(completed) / \(count)")
-            }
-            if imageGenerator.generate(version: image) {
+            guard imageGenerator.needsToGenerate(image) else {
                 results.created(outputFile: image.outputPath)
+                didFinishOneImage()
                 continue
             }
-            results.failed(image: image)
+            if image.type == .avif {
+                avifImagesToGenerate.append(image)
+            } else {
+                newImagesToGenerate.append(image)
+            }
+        }
+
+        func generate(images: [ImageVersion]) {
+            for image in images {
+                guard shouldGenerateWebsite else { return }
+                defer { didFinishOneImage() }
+                if imageGenerator.generate(version: image) {
+                    results.created(outputFile: image.outputPath)
+                    continue
+                }
+                results.failed(image: image)
+            }
+        }
+
+        generate(images: newImagesToGenerate)
+        generate(images: avifImagesToGenerate)
+        if completed != count {
+            print("Expected \(count) images processed, but only \(completed) were")
         }
     }
 
diff --git a/CHDataManagement/Views/Generation/GenerationContentView.swift b/CHDataManagement/Views/Generation/GenerationContentView.swift
index 20171da..a62f3bc 100644
--- a/CHDataManagement/Views/Generation/GenerationContentView.swift
+++ b/CHDataManagement/Views/Generation/GenerationContentView.swift
@@ -71,6 +71,9 @@ struct GenerationContentView: View {
             GenerationStringIssuesView(
                 text: "unsaved output files",
                 items: $content.results.unsavedOutputFiles)
+            GenerationStringIssuesView(
+                text: "failed image generations",
+                items: $content.results.failedImages) { $0.outputPath }
             GenerationStringIssuesView(
                 text: "missing files",
                 items: $content.results.missingFiles)