diff --git a/chrome/browser/download/insecure_download_blocking.cc b/chrome/browser/download/insecure_download_blocking.cc
index b79cb917c7c5b..86361fd596bbd 100644
--- a/chrome/browser/download/insecure_download_blocking.cc
+++ b/chrome/browser/download/insecure_download_blocking.cc
@@ -217,6 +217,23 @@ struct InsecureDownloadData {
     // used for Chrome stuff. Background fetch should probably be HTTPS-only.
     auto download_source = item->GetDownloadSource();
     auto transition_type = item->GetTransitionType();
+    LOG(ERROR) << "[POC] InsecureDownloadData: url=" << dl_url
+               << " transition_type=" << static_cast<int>(transition_type)
+               << " (core="
+               << (static_cast<int>(transition_type) &
+                   static_cast<int>(ui::PAGE_TRANSITION_CORE_MASK))
+               << ", "
+               << ui::PageTransitionGetCoreTransitionString(transition_type)
+               << ")";
+    LOG(ERROR) << "[POC]   broken-check (transition & TYPED)="
+               << (static_cast<int>(transition_type) &
+                   static_cast<int>(ui::PAGE_TRANSITION_TYPED))
+               << "  (transition & AUTO_TOPLEVEL)="
+               << (static_cast<int>(transition_type) &
+                   static_cast<int>(ui::PAGE_TRANSITION_AUTO_TOPLEVEL))
+               << "  (transition & RELOAD)="
+               << (static_cast<int>(transition_type) &
+                   static_cast<int>(ui::PAGE_TRANSITION_RELOAD));
     if (download_source == DownloadSource::RETRY ||
         (transition_type & ui::PAGE_TRANSITION_RELOAD) ||
         (transition_type & ui::PAGE_TRANSITION_TYPED) ||
@@ -272,6 +289,11 @@ struct InsecureDownloadData {
            !download_delivered_securely) &&
           !net::IsLocalhost(dl_url);
     }
+    LOG(ERROR) << "[POC]   is_mixed_content_=" << is_mixed_content_
+               << " is_insecure_download_=" << is_insecure_download_
+               << " initiator="
+               << (initiator_.has_value() ? initiator_->GetURL().spec()
+                                          : "(none)");
 
     // A download is considered initiated from a trusted WebUI (e.g. chrome://)
     // if either:
@@ -413,6 +435,8 @@ InsecureDownloadStatus GetInsecureDownloadStatusForDownload(
 
   // If the download is fully secure, early abort.
   if (!data.is_insecure_download_) {
+    LOG(ERROR) << "[POC] GetInsecureDownloadStatusForDownload -> SAFE "
+                  "(is_insecure_download_=false)";
     return InsecureDownloadStatus::SAFE;
   }
 
@@ -432,6 +456,10 @@ InsecureDownloadStatus GetInsecureDownloadStatusForDownload(
         ContainsExtension(kSafeExtensions, data.extension_)) {
       return InsecureDownloadStatus::SAFE;
     }
+    LOG(ERROR)
+        << "[POC] GetInsecureDownloadStatusForDownload -> BLOCK (bypassable "
+           "warning) -- BUG: mixed-content classification was lost due to "
+           "broken bitwise-AND on PageTransition core value";
     return InsecureDownloadStatus::BLOCK;
   }
 
@@ -454,6 +482,8 @@ InsecureDownloadStatus GetInsecureDownloadStatusForDownload(
       return InsecureDownloadStatus::BLOCK;
     }
 
+    LOG(ERROR) << "[POC] GetInsecureDownloadStatusForDownload -> SILENT_BLOCK "
+                  "(hard block, no user override)";
     return InsecureDownloadStatus::SILENT_BLOCK;
   }