diff --git a/lib/pretty_text.rb b/lib/pretty_text.rb
index 0ed10099efd..8dea3107554 100644
--- a/lib/pretty_text.rb
+++ b/lib/pretty_text.rb
@@ -449,9 +449,16 @@ module PrettyText
         img['src']
       end
 
-      width = img.classes.include?('site-icon') ? 16 : img['width']
-      height = img.classes.include?('site-icon') ? 16 : img['height']
-      oneboxed = (img.parent&.parent&.classes || []).include?('onebox-body')
+      width = img['width']
+      height = img['height']
+      oneboxed = img.ancestors.css(".onebox-body").any? || img.classes.include?("onebox-avatar")
+
+      # we always want this to be tiny and without any special styles
+      if img.classes.include?('site-icon')
+        oneboxed = false
+        width = 16
+        height = 16
+      end
 
       if Upload.secure_media_url?(url)
         img.add_next_sibling secure_media_placeholder(doc, url, oneboxed: oneboxed, width: width, height: height)
diff --git a/spec/components/email/styles_spec.rb b/spec/components/email/styles_spec.rb
index 8776d5019a4..382f1a11d64 100644
--- a/spec/components/email/styles_spec.rb
+++ b/spec/components/email/styles_spec.rb
@@ -330,6 +330,38 @@ describe Email::Styles do
         expect(@frag.css('[data-embedded-secure-image]')[0].attr('style')).to eq('width: 16px; height: 16px;')
         expect(@frag.css('[data-embedded-secure-image]')[1].attr('style')).to eq('width: 60px; max-height: 80%; max-width: 20%; height: auto; float: left; margin-right: 10px;')
       end
+
+      context "when inlining a oneboxed image with a direct parent of onebox-body" do
+        let(:html) do
+          <<~HTML
+<aside class="onebox allowlistedgeneric">
+  <header class="source">
+      <img src="#{Discourse.base_url}/secure-media-uploads/original/1X/#{siteicon.sha1}.ico" class="site-icon" width="64" height="64">
+      <a href="https://test.com/article" target="_blank" rel="noopener" title="02:33PM - 24 October 2020">Test</a>
+  </header>
+  <article class="onebox-body">
+    <img src="#{Discourse.base_url}/secure-media-uploads/original/1X/123456.png" class="thumbnail onebox-avatar" width="20" height="30">
+
+<h3><a href="https://test.com/article" target="_blank" rel="noopener">Test</a></h3>
+
+<p>This is a test onebox.</p>
+
+  </article>
+  <div class="onebox-metadata">
+  </div>
+  <div style="clear: both"></div>
+</aside>
+          HTML
+        end
+
+        it "keeps the special onebox styles" do
+          strip_and_inline
+          expect(@frag.to_s).to include("cid:email/test.png")
+          expect(@frag.to_s).to include("cid:email/test2.ico")
+          expect(@frag.css('[data-sripped-secure-media]')).not_to be_present
+          expect(@frag.css('[data-embedded-secure-image]')[1].attr('style')).to eq('width: 60px; max-height: 80%; max-width: 20%; height: auto; float: left; margin-right: 10px;')
+        end
+      end
     end
   end
 end