diff --git a/plugins/hosts/windows/cap/smb.rb b/plugins/hosts/windows/cap/smb.rb
index 9287957bb..d224e06a3 100644
--- a/plugins/hosts/windows/cap/smb.rb
+++ b/plugins/hosts/windows/cap/smb.rb
@@ -64,7 +64,10 @@ module VagrantPlugins
             # Check if this name is already in use
             if share_info = current_shares[data[:smb_id]]
               if !hostpath.empty? && share_info["Path"].downcase != hostpath.downcase
-                raise "share in use with different path"
+                raise SyncedFolderSMB::Errors::SMBNameError,
+                  path: hostpath,
+                  existing_path: share_info["Path"],
+                  name: data[:smb_id]
               end
               @@logger.info("skip creation of existing share name=#{name} id=#{data[:smb_id]}")
               next
@@ -98,7 +101,7 @@ module VagrantPlugins
         def self.existing_shares
           result = Vagrant::Util::PowerShell.execute_cmd("Get-SmbShare|Format-List")
           if result.nil?
-            raise "failed to get existing shares"
+            raise SyncedFolderSMB::Errors::SMBListFailed
           end
           shares = {}
           name = nil
diff --git a/plugins/synced_folders/smb/errors.rb b/plugins/synced_folders/smb/errors.rb
index ebb9bbef3..761924207 100644
--- a/plugins/synced_folders/smb/errors.rb
+++ b/plugins/synced_folders/smb/errors.rb
@@ -18,6 +18,14 @@ module VagrantPlugins
         error_key(:credentials_missing)
       end
 
+      class SMBListFailed < SMBError
+        error_key(:list_failed)
+      end
+
+      class SMBNameError < SMBError
+        error_key(:name_error)
+      end
+
       class DefineShareFailed < SMBError
         error_key(:define_share_failed)
       end
diff --git a/templates/locales/synced_folder_smb.yml b/templates/locales/synced_folder_smb.yml
index 79eb93aef..3521ff4ff 100644
--- a/templates/locales/synced_folder_smb.yml
+++ b/templates/locales/synced_folder_smb.yml
@@ -55,6 +55,18 @@ en:
         Stderr: %{stderr}
 
         Stdout: %{stdout}
+      name_error: |-
+        Vagrant is unable to setup a requested SMB share. An SMB share already
+        exists with the given name.
+
+        Share name: %{name}
+
+        Current path: %{existing_path}
+
+        Requested path: %{path}
+      list_failed: |-
+        Vagrant failed to generate a list of local SMB shares. Please try
+        running the command again.
       no_routable_host_addr: |-
         We couldn't detect an IP address that was routable to this
         machine from the guest machine! Please verify networking is properly