diff --git a/CHANGELOG.md b/CHANGELOG.md
index 013e757ec..335e804e0 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -18,6 +18,8 @@ BUG FIXES:
   - commands/package: Nice error if includes contain symlinks. [GH-3200]
   - commands/rsync-auto: Don't crash if the machine can't be communicated
       to. [GH-3419]
+  - communicators/ssh: Only show connection warnings after three connection
+      attempt failures. [GH-3442]
   - guests/coreos: Docker provisioner works. [GH-3425]
   - guests/fedora: Fix hostname setting. [GH-3382]
   - guests/fedora: Support predictable network interface names for
diff --git a/plugins/communicators/ssh/communicator.rb b/plugins/communicators/ssh/communicator.rb
index f9c76c4f6..fb9789bea 100644
--- a/plugins/communicators/ssh/communicator.rb
+++ b/plugins/communicators/ssh/communicator.rb
@@ -52,8 +52,10 @@ module VagrantPlugins
           ssh_auth_type = "password" if ssh_info[:password]
           @machine.ui.detail("SSH auth method: #{ssh_auth_type}")
 
+          attempts = 0
           while true
-            message = nil
+            attempts +=1
+            message  = nil
             begin
               begin
                 connect(retries: 1)
@@ -82,7 +84,9 @@ module VagrantPlugins
               # Ignore it, SSH is not ready, some other error.
             end
 
-            if message
+            # Start showing warning messages after the 3rd attempt, since
+            # the first couple are usually just waiting for actual booting.
+            if message && attempts >= 3
               @machine.ui.detail("Warning: #{message} Retrying...")
             end
           end