diff --git a/app/lib/text_formatter.rb b/app/lib/text_formatter.rb
index 7fbb6fce1..c1b0a8165 100644
--- a/app/lib/text_formatter.rb
+++ b/app/lib/text_formatter.rb
@@ -68,6 +68,12 @@ class TextFormatter
       suffix      = url[prefix.length + 30..]
       cutoff      = url[prefix.length..].length > 30
 
+      if suffix && suffix.length == 1 # revert truncation to account for ellipsis
+        display_url += suffix
+        suffix = nil
+        cutoff = false
+      end
+
       tag.a href: url, target: '_blank', rel: rel.join(' '), translate: 'no' do
         tag.span(prefix, class: 'invisible') +
           tag.span(display_url, class: (cutoff ? 'ellipsis' : '')) +
diff --git a/spec/lib/text_formatter_spec.rb b/spec/lib/text_formatter_spec.rb
index bde17bb79..a71655ed2 100644
--- a/spec/lib/text_formatter_spec.rb
+++ b/spec/lib/text_formatter_spec.rb
@@ -50,7 +50,7 @@ RSpec.describe TextFormatter do
       end
     end
 
-    context 'when given a stand-alone google URL' do
+    context 'when given a stand-alone Google URL' do
       let(:text) { 'http://google.com' }
 
       it 'matches the full URL' do
@@ -280,6 +280,26 @@ RSpec.describe TextFormatter do
       end
     end
 
+    context 'when given a lengthy URL' do
+      let(:text) { 'lorem https://prepitaph.org/wip/web-dovespair/ ipsum' }
+
+      it 'truncates the URL' do
+        expect(subject).to include '<span class="invisible">https://</span>'
+        expect(subject).to include '<span class="ellipsis">prepitaph.org/wip/web-dovespai</span>'
+        expect(subject).to include '<span class="invisible">r/</span>'
+      end
+    end
+
+    context 'when given a sufficiently short URL' do
+      let(:text) { 'lorem https://prepitaph.org/wip/web-devspair/ ipsum' }
+
+      it 'does not truncate the URL' do
+        expect(subject).to include '<span class="invisible">https://</span>'
+        expect(subject).to include '<span class="">prepitaph.org/wip/web-devspair/</span>'
+        expect(subject).to include '<span class="invisible"></span>'
+      end
+    end
+
     context 'when given text containing a hashtag' do
       let(:text)  { '#hashtag' }