Two recent reader requests have something in common: Neither reader got the answer they hoped for. Michael wants Word to remember his collapsed and expanding heading configuration from one work session to another. Tyrell wants to automate the process of creating and delaying an email message. As you’ll soon learn, I was able to get them close with easy solutions, but neither receives a 100% solution.

I’m using Office 365’s desktop version of Word and Outlook. You can use earlier versions of Outlook; Word added the collapsible heading feature in 2013. You can work with your own Word document or download the Word demonstration .docx file. Neither solution works in the online versions.

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Collapsible headings by default

After reading the article, How to use Word 2013’s collapsible headings, Michael asked if Word can “remember,” which settings are collapsed or expanded by saving the file. Unfortunately, the feature doesn’t work that way–it would be nice, though wouldn’t it? The closest you can get is to change the collapsible default property for the headings you want collapsing most often. Then, you can tweak as needed each time you open the document. It’s not a silver bullet, but it’ll get you a bit closer to what you want.

Now, let’s run through a quick example. First, the simple document in Figure A has five headings:

  • Online Video is Heading 1
  • Professional Looking Documents is Heading 2
  • Themes and Styles and Button-quick Layout are both Heading 3
  • Reading View is Heading 1

Now, let’s suppose that you want the document to always open with the Heading 2 headings always collapsed. To arrange this, do the following:

  1. Select the sections you want to collapse (Figure B). Because this is a hierarchical feature, you only need to set the property for the highest heading–in this case, Professional Looking Documents.
  2. Click the dialog launched (circled) in the Paragraph group (on the Home tab).

In the resulting dialog, check the Collapsed by default option and click OK. Figure C shows the results.

To test what you’ve done, save the document, close and then reopen it. The Heading 2 and Heading 3 sections stay collapsed from one work section to another until you disable the Collapsed by default setting. If you expand the sections and save the document, Word will still collapse the headings when you open the document the next time.

This simple example doesn’t show this property’s true strength. In a large document, you’ll find this is a handy way to work, whether you’re creating or distributing the document to others.

Delay message

Tyrell sends a reminder email to several people every month, and he wants to control when it’s sent. You could automate this process with a custom task form, but that takes specialized knowledge. An easier route might be to delay the send and update it each month. You’ll have to remember to reset the send date, but if you don’t know how to create a custom task form, this shorter route will get the job done. Here’s how to delay the send time for a message:

  1. Open a new message and enter the recipients, subject, and text.
  2. In the More Options group, click Delay Delivery.
  3. In the Delivery Options section, click Delay Delivery.
  4. In the Delivery options section, set the date and time Outlook should send the message (Figure D). The default is 5PM for the current day, and I know of no way to change this setting.
  5. Close the message.

You can uncheck the Do Not Deliver Before option at any time to send the message immediately. If you are offline at the delivery time, Outlook will send the message when you connect; Outlook must be open though. Outlook can’t send messages when it’s closed. You can edit the email if needed without triggering a send.

The good news is that you don’t have to recreate the full message each month. Instead, find the message in your Send folder and open it. Click Reply All (that part’s important to get the full recipient list) and repeat the delay receipt instructions above. Be sure to delete the header from the message so the email looks new and not like a reply.

As I said, it’s not the best solution, but it’ll get you closer to what you want. If you do this a lot, it might be worth the expense to hire an Outlook developer to create the custom task forms you need.

Send me your question about Office

I answer readers’ questions when I can, but there’s no guarantee. Don’t send files unless requested; initial requests for help that arrive with attached files will be deleted unread. You can send screenshots of your data to help clarify your question. When contacting me, be as specific as possible. For example, “Please troubleshoot my workbook and fix what’s wrong” probably won’t get a response, but “Can you tell me why this formula isn’t returning the expected results?” might. Please mention the app and version that you’re using. I’m not reimbursed by TechRepublic for my time or expertise when helping readers, nor do I ask for a fee from readers I help. You can contact me at

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