outlook not properly sending messages, they are getting stuck in outbox and the icon shows a pencil edit icon instead of the usual envelope icon. What's the fix?

• When a message gets stuck in the Outbox, the most likely cause is a large attachment.
• Click Send/Receive and look at the Work Offline button. If it’s blue, you’re disconnected. Click it to connect (the button turns white) and click Send All.
• If the Exchange email account is set to use Cached Exchange mode and “LoadTransportProviders” registry value is set to 1, the message is not sent immediately. Use Online mode profile for your Microsoft Exchange Server mailbox or delete the value of LoadTransportProviders in the registry.
• Outlook may hang at loading profile or won’t start after updating to Current Channel Version 1905 (Build 11629.20196) or higher. It can be fixed by ending all the Office processes that are running and disabling certain presence features, like “Display online status next to name” and “Show user photographs when available”.
• If emails are not sending from Outlook.com, check to see if the stuck email is in the Drafts or Outbox folder, and if the message has an attachment larger than 25MB. If the Inbox is full, empty the junk folder.
• Outlook 2007 and Outlook 2003 - If the Send immediately when connected option is not enabled, select it to resolve the issue.
• Outlook 2010 and later versions - If the Send immediately when connected option is not enabled, select it to resolve the issue.
• Outlook may display an error telling you that Outlook is trying to transmit the message. Afterward, you may close Outlook if it does not close itself.
• If Outlook doesn’t close, press Ctrl+Alt+Delete and click Start Task Manager. In Task Manager, click the Processes tab, scroll down to outlook.exe, and click End Process.
• When you send an e-mail message in Microsoft Outlook, the message may remain in your Outbox folder until you manually initiate a Send/Receive operation (for example, press F9 or select send or receive).
• Outlook keeps your drafts, deleted items, and copied items. For drafts, open the email and click Send.
• For other messages, recover them by clicking Deleted Items > select the message or messages > Move > Other Folder > select the folder where you want to move the message.
• A message can get stuck if it includes an unresolved recipient, or if the recipient address includes a distribution list that has not been expanded.
• If there is an issue with your account or an issue with sending a message, you’ll often receive an error message. Read

• When a message gets stuck in the outbox, it may be caused by a large attachment.
• To fix the issue, click “SEND/RECEIVE” > “Work Offline”.
• Then, in the navigation pane, click “Outbox”.
• To fix the stuck message, you can either delete it or drag it to the drafts folder.
• If an error occurs, Outlook may be trying to transmit the message. Close Outlook and go to Task Manager to end all outlook.exe processes. Then, reopen Outlook and repeat Steps 2-3.
• If you are disconnected, click “SEND/RECEIVE” and make sure that the “Work Offline” button is not highlighted. If it is, click on it to connect and then click “Send All”.
• Emails may get stuck in the outbox if the email was opened and closed while it was in the outbox.
• To fix this, double-click on the email and click “Send”.
• Emails can also get stuck in the outbox if they have a very large attachment.
• If your email provider blocks emails with attachments larger than a certain size, it is not recommended to send attachments larger than a few megabytes.
• When you double-click on the email and get an error, Outlook may still be trying to send emails in the outbox. You can’t open or delete an email when this is happening.
• You can open emails that aren’t actively being sent if there are multiple emails in the outbox or if Outlook isn’t connected to your email server.
• To disconnect Outlook from your email server, click the “SEND/RECEIVE” tab and then click the “Work Offline” button.
• If you still get an Outlook error after double-clicking on the email, close Outlook, sign out of Windows, sign back in to Windows, and start Outlook.
• To fix the email, click and hold on the email in the outbox and drag it to the “Drafts” folder.
• Alternatively, deleting the email will also work if you want to start over.
• To resume sending and receiving emails, click the “SEND/RECEIVE” tab and click the “Work Offline” button again.
• To save a large attachment, right-click the attachment and click “Save As”.
• If you are sending the email from work, save the attachment to a network location and copy the path to the file on the network location. If you are sending from home, save the attachment to an Internet file sharing service, such as

• The webpage provides several methods to try and fix the issue of messages piling up in the Outlook outbox or not being received by the recipients.
• One possible cause of the issue mentioned is a full Microsoft cloud storage which prevents sending or receiving emails. Checking mailbox storage to see what’s taking up space is advised.
• The webpage advises to toggle between offline and online mode in Outlook if the status says Disconnected, Working Offline, or Trying to connect.
• It suggests checking internet connectivity if losing connection is the issue. The following steps can be followed to troubleshoot:
  • Open a browser, such as Internet Explorer, Edge, or Chrome.
  • Try entering one of the Microsoft websites or Bing in the address bar.
• Some email providers (such as your ISP or even Gmail) won’t let you send messages larger than a certain size. 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 see Authentication Failed, learn what to do if you have 2-step verification turned on.
• If that message has an attachment that’s larger than 5MB, delete the attachment and either attach a smaller file or attach a link to the attachment. See Attach a file to an email in Outlook for more information on attachments.
• If you’ve changed your password on the website for your email account, you’ll need to change it in Outlook, too. Choose File > Account Settings > Account Settings.
• If Outlook is not sending only some Outbox emails, make sure that Outlook is set to work online and check the status of your antivirus software if installed.
• If you are using an Exchange account that is configured with Cached Exchange Mode, Outlook may become stuck in limbo when trying to delete messages. Clearing out the folder and/or clearing the Outlook cache should help.
• Delete any suspicious emails or suspected phishing emails from your mailbox.
• For many types of email accounts, Outlook stores your messages in a Personal Folders File (.pst file). You can repair this file by running the Inbox Repair Tool. This repair should take approximately fifteen minutes.
• Disable all add-ins, you can start Outlook in safe mode or use the /safe command line switch (winword /safe) when starting the application. See Enable or disable add-ins in Office programs for more information.
• Repairing Office should fix any corrupted files that were installed with Office. For more information on repairing files, see Repair an Office application.

Instructions not clear. The original webpage has more than 1500 words. Please provide additional guidance.

I apologize, but it seems that the website provided did not contain 400 words of relevant information. Nonetheless, below are the relevant bullet points from the webpage:

• When an email is sent in Outlook, it may remain in the outbox folder.
• This issue can occur if the “Send immediately when connected” option is not enabled.
• This setting is tied to the following registry data in the Outlook version: HKEY_CURRENT_USER\Software\Microsoft\Office<x.0>\Outlook\Options\Mail or Policy key: HKEY_CURRENT_USER\Software\Policies\Microsoft\Office<x.0>\Outlook\Options\Mail
• The value of this DWORD “Send Mail Immediately” should be “0”.
• For Outlook 2010 and newer, this option can be enabled by navigating to Options > Advanced > Send and receive section > Send immediately when connected.
• For Outlook 2007 and 2003, this option can be enabled by navigating to Tools > Options > Mail Setup tab > Send/Receive Section > Send immediately when connected.
• If this option is grayed out, it may be managed by group policy, and an administrator would need to remove the group policy.
• The article was written on 07/21/2022 and pertains to Outlook 2019, Outlook 2016, Outlook 2013, Microsoft Outlook 2010, Microsoft Office Outlook 2007, Microsoft Office Outlook 2003, Outlook for Microsoft 365.

• Title of the webpage: Emails being sent but stuck in Outbox
• URL: https://www.reddit.com/r/Outlook/comments/mhrhcb/emails_being_sent_but_stuck_in_outbox/
• The post was made 2 years ago in the r/Outlook subreddit.
• The user is experiencing issues with their emails getting stuck in the Outbox and not being moved to sent items in Outlook.
• The user has a shared mailbox and a personal mailbox.
• When the user sends emails from the personal mailbox, other users receive those emails, but they are still stuck in the Outbox.
• The default behavior should put the emails into the personal sent box, but that is not happening.
• The issue might be related to the settings for shared mailboxes.
• There is a reg key that controls whether a shared sent item will go to the shared sent box or personal sent box.
• Some users suggest that the issue could be related to an OST file issue.
• One user recommends turning off cached mode, which may help resolve the issue as it may be related to an OST file issue.
• Another user suggests creating a new Outlook profile to fix the issue.
• A bot warns users not to post personal information, such as email address or product key, to protect their privacy.
• The bot also instructs users to set their flair status to Open if they need help, and to contact Microsoft Support for help with scammers or third-party commercial products/services.
• The post has a total of 2 points and 2 comments.
• The first comment is made by another user who welcomes the original poster and warns them about posting personal information.
• The second comment, made by another user, suggests that the issue is related to an OST file issue and that turning off cached mode may help. This comment has 1 karma.

• User cannot send an email on Outlook desktop application, and it shows as disconnected at the bottom of the screen, even though the internet connection is fine.
• The email is for university work, so the user cannot use another service.
• User also experiences issues with the Outlook Android app, as the app will not sign in and the user misses important communications due to the lack of alerts on the phone.
• User has contacted IT before about app issues, but they have only recommended resetting the account and going through the troubleshooter for the application.
• The email gets stuck in outbox and never actually sends.
• The user has tried resetting the account, deleting the account and re-adding it, and reinstalling the app.
• Another user recommends running a ‘repair’ in Account Settings to fix the issue.
• Another user suggests rebooting and disconnecting the VPN before running a repair.
• The repair option can be accessed by going to File->Account Settings->Repair in the desktop application.
• One user did not have the option to find the Repair option in Account Settings, but it may be found on the second row of menu options.
• A reddit bot cautions against posting personal information on the public community and recommends contacting Microsoft Support for help.

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