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Outlook Emails Fail to Send

 

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There is a long list of reasons why outlook messages are not sending. Outlook has a few of its own snafus.

  • The email account isn't set up (correctly):
  • In Outlook go to Tools > Account Settings > New and create the new account. For correct settings search Google for 'smtp settings' + [the name of your email client] like 'smtp settings Outlook'. Once completed click on Test Account Settings. If either send or receive or both fail, it may take some effort to pay attention to details to achieve correct settings. The primary errors are using (or not using) the full email address for the User Name, wrong Password and incorrect POP3 and/or SMTP addresses.

  • Is Outlook in Offline Mode?
  • Click on File then uncheck 'Work Offline' if it is checked (activated).

    Click on More Settings and again, acquire the correct settings from the search results above.

  • One message sends from the same account but another doesn't go out.
  • Try sending the email without an attachment. If it sends, the attachment was the issue. Cheap (free) email services like Yahoo limit attachments to 2MB. Gmail is 25MB. If you're using 'free email services' for your business then there lies 'the problem with email'.

  • The attachment wasn't the problem.
  • Some email programs are very fussy about the To: Address. There can be no punctuation or 'mailto' included in the address. Outlook (being the trashed-out program that it is) will get cantankerous over how the To: Address was entered. If the address was selected from the list of suggested addresses, check the address (by using another email service), or type the address instead of selecting it from the list of suggested addresses. Sometimes replying to an email fails because the email address was not entered correctly from the sender. (Anyone can enter anything in the From: Field when sending an email. That's a common practice amongst spammers.)

  • Outlook Outgoing Messages Wont Send
  • Another issue with Outlook is settings seemingly changing without our knowledge. RIGHT click on the email sitting in the out box and select Message Options. Remove the check in 'Do not deliver before' and click Close. Click on Send/Receive to see if this was the issue. See if you can determine why the message was marked for 'delayed send': Open a new blank email. Before entering anything, check Delayed Send to see if there is an entry. If so consider deleting any rules related to delayed sending.

  • Other Causes
  • There may be a rule that is governing sent messages. Click on Tools > Rules and Alerts and look for a rule starting with 'Delay'. If it shouldn't be there, select it and press Delete.

    Conversely, it may be useful to make the program hold sent messages in the outbox for a period of time you specify (giving time for afterthoughts, changes, regrets...). To delay the sending of all emails by a designated amount of time, click on New > Check messages after sending > Next > Next > Yes (to 'This rule will be applied to every message you send. Is this correct?'). Check 'defer delivery by a number of minutes'. Enter the number of minutes to delay and click Next. To have the program ignore the delay for messages you mark as 'High Important' check 'except if it [the message] is marked as importance'. In the bottom window click on 'importance' and choose 'High'. Click Next and type a name for the rule. Start with 'Delay' so the rule can be found more easily later on. Make sure 'Turn on this rule' is checked. Click Finish.

  • A Trick
  • When an email is stuck in the outbox, move it to the inbox, click to reopen it, click Send. Click on Send/Receive to see if it gets sent. This has worked sporadically. Sorry: Can't say why.

  • New Discovery - Recorded Addresses (Autocomplete)
  • Remember the email address of the recipient in the To: Field. Remove it and start typing the address one letter or number at a time. If the email address is saved in Outlook's AutoComplete list, see if the troubled email address has quotes before and after it. If so, continue complete all but the last letter of the email address then use the down arrow if necessary to scroll down to the saved address with quotes and hit the delete. Type the last letter of the email address and send it.

  • Outlook Messages Not Being Sent
  • Move the message(s) to the drafts folder. Click on File then Work Offline. Open the message(s) in Drafts and resend them, making sure the To: address isn't encased in single quote marks. (If it is, double click on the address, copy the address without quotes, remove the address from the To: field and past the address into the To: field. Send. Go back to File and remove 'Work Offline'. Messages might send after this round of hoop jumping. If not, try holding your mouth in a different way and try again.

    Fairly often the resolution has been to send the email via another client (like webmail) and delete the message from Outlook. Of course that doesn't discover a solution to the issue.

  • Another Discovery: When an email gets 'stuck' right click on it in the outbox and click forward. The email will still be addressed to the same recipient(s) and seems to go out without a hitch. Delete the stuck version.

  • Also, removing all rules related to delayed sending now allows messages to go out right away.

These discoveries were made after the bomb went off on this computer uninstalling the trial version of Office 365. At first it looked like the calamity required an update of Outlook to 2013 which was done. That wouldn't work with TEmplate Phrases so Outlook 2007 was restored and all 51,000 emails had to be downloaded from the server again. Then permissions became a problem making it necessary to activate the 'super administrator' account and run programs from that account, requiring all 51,000 emails to be downloaded from the server again. Friggin' Microsoft!

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