diff --git a/lib/jirahelper/regex.rb b/lib/jirahelper/regex.rb
index 5fb83e1..7a29bab 100644
--- a/lib/jirahelper/regex.rb
+++ b/lib/jirahelper/regex.rb
@@ -8,6 +8,6 @@ module Regex
     PROJECT_PATTERN = /(?<project>[a-zA-Z0-9]{1,10})/
     ISSUE_PATTERN   = /(?<issue>#{PROJECT_PATTERN}-[0-9]{1,5}+)/
     EMAIL_PATTERN   = /(?<email>[\w+\-.]+@[a-z\d\-]+(\.[a-z]+)*\.[a-z]+)/i
-    AMBIENT_PATTERN = /\s#{ISSUE_PATTERN}/
+    AMBIENT_PATTERN = /(\s|^)#{ISSUE_PATTERN}/
   end
 end
diff --git a/spec/lita/handlers/jira_spec.rb b/spec/lita/handlers/jira_spec.rb
index c24a6a7..6cfe2a9 100644
--- a/spec/lita/handlers/jira_spec.rb
+++ b/spec/lita/handlers/jira_spec.rb
@@ -189,9 +189,10 @@
       end
 
       it 'shows details for a detected issue in a message' do
+        send_message('XYZ-987')
         send_message('foo XYZ-987 bar')
         send_message('foo XYZ-987?')
-        expect(replies.size).to eq(2)
+        expect(replies.size).to eq(3)
       end
 
       it 'does not show details for a detected issue in a command' do
@@ -200,8 +201,10 @@
       end
 
       it 'does not show details for a issue in a URL-ish context' do
+        send_message('http://www.example.com/XYZ-987')
         send_message('http://www.example.com/XYZ-987.html')
         send_message('http://www.example.com/someother-XYZ-987.html')
+        send_message('TIL http://ruby-doc.org/core-2.3.0/Enumerable.html#method-i-each_slice')
         expect(replies.size).to eq(0)
       end