Adding pictures and large attachments to your message can prevent you from sending that message and any messages sent after the large message. If you can't reach either of those two websites, see Fix network connection issues in Windows Some email providers such as your ISP or even Gmail won't let you send messages larger than a certain size. Still need help? If you see Disconnected, Working Offline, or Trying to connect…, Outlook can't reach the email server to send your mail. Start Outlook, and then test to see whether the issue is resolved by sending an email message as the distribution group. The contents of the folder will be re-created when you restart Outlook. Delete the contents of the Offline Address Books folder. To unhide it, select Start, type folder options in the search box, select Folder Options, select the View tab, select Show hidden files, folders, and drives, and then select OK. In Windows 8 and Windows 7, the folder is located along the following path. Delete all files and folders in the Offline Address Books folder. When you create the message, use the global address list GAL to populate the From field. Test to see whether the issue is resolved by sending an email message as the distribution group.

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