Troubleshooting tips: Can’t add attachments to emails: Office 365

When attempting to send an email, particularly within Microsoft Outlook, you will no doubt look to add attachments with emails at least once every now and again. Sometimes though, you may run into issues as you look to utilise the attachment feature of sending an email. Chances are, if you are here reading this article today, then that is a problem that has been afflicting you.

There are several reasons as to why you may not be able to add attachments to your email. The most likely cause is that the file you are trying to send is far too oversized for the email, but that isn’t to say that this is the only cause. 

Though there are numerous solutions, this article will explore only one of the many potential solutions for you, the user, in answer to the issue of not being able to add attachments to your emails within Microsoft Office 365. The solution that we will be looking at is changing the sharing preferences within your Microsoft Outlook application.

Now, it would hardly be fair to expect you to understand the solution after all we’ve done so far is tell you what it is. Course, I shouldn’t discredit anyone, as there may well be some people who know what to do with the above information alone. If not though, don’t worry, as we will go on to explore each method in further detail below.

First, we will offer you a step by step list to guide you through the process. A swift explanation, the lists may serve some of you enough to go away and complete the fixes for your email attachment issues.

If not though, read on, as after the list we will offer you a more thorough, more complete breakdown of the process. This section will contain an explanation of far greater detail, and will be complete with annotated screenshots to accompany each step, in order to ensure that we are providing you with as much assistance as we can.

So, first, we will look at the steps of changing the sharing preferences within your Microsoft Outlook application.

Step by step: Changing outlook sharing preferences to add attachments to emails

  • Open your Microsoft Outlook inbox.
  • From here, look towards the top of your screen.
  • Now, towards the right hand side, there should be a cog icon.
  • This represents the settings menu of your Outlook application. Click it.
  • Then, a small menu should appear to you.
  • At the bottom of this menu should be an option that reads ‘View all Outlook settings’. Click on this.
  • Now, you should be greeted with a popup menu of Outlook settings.
  • Look to the left of this menu, where there is a list of all the subsections of options.
  • Here, make sure you are on the ‘Email’ tab.
  • From the ‘Email’ tab, navigate to the subsection that is titled ‘Attachments’.
  • Here, you will be able to see the sharing preferences of your Outlook application.

So, your first step will be to open your Microsoft Outlook inbox. Once here, you will be on the main screen of your email, or at least, you should be. From here, you will need to look towards the top of your screen, towards the right hand corner. Here, there should be a cog icon that represents the settings of your Outlook. Click on this icon.

Clicking the settings cog will trigger a small menu to appear on the right hand side of your screen. On this menu, at the bottom of it, there will be a small prompt asking you if you want to view all Outlook settings. Click on this. Should you need any further assistance, it has been highlighted in the below screenshot.

Opting to view all Outlook settings will, in a particularly unsurprising fashion, show you all the Outlook settings that you are able to browse and edit. By default, you should find yourself in the subsection of options titled ‘Email’. You will be able to see this by looking to the very left hand side of your screen, where you will see a list of four option headings.

So, once you have ensured that you are on the email tab of options, you will then want to look to the subtopics of email settings that you can edit. In case you are confused, you will now want to be reading down the second list from your left, the longer one when compared to the list of general subheadings.

On this options list, you will want to click the subheading ‘Attachments’, which is the third option from the top. Again, should you need further guidance, there will as always be a highlighted screenshot to point you in the right direction beneath this passage of text.

After clicking ‘Attachments’, you will be brought to that very bracket of email options within your overall Outlook settings hub. Here, you will be able to edit the sharing preferences of your Outlook in the manner of two questions, to which you can set a preference with a bullet pointed answer, one of three in fact.

Initially, you are asked for your preferences for files that you choose from OneDrive. Here, of the three potential answers you can give, you should look to click the top option that reads, “Ask me how I want to share them every time”, to ensure that you have complete control, or at least more control, over certain email aspects such as adding attachments.

Located just underneath this selection is the second of the two questions. Here, you will be asked how you would like your sharing preferences to be for files you choose from group files. Again, you will have three bullet point options to choose from. Here, you will want to choose the middle option, which should read, “Always share them as OneDrive links”.

Now, if such a process being explained is confusing when viewed only as text, don’t worry, as just below this text we will show you a screenshot of the ‘Attachments’ menu with the correct settings selected and then highlighted, in order to further demonstrate to you where they should be.

This change will autosave, and so you don’t need to spend time looking for a way to manually save it. After selecting these two options, you will have successfully completed the process!

Thank you for taking the time to read this blog, I hope you found it as helpful as you wanted it to be! As always, please don’t hesitate to get in touch with a member of our team if you encounter any sort of issue or simply have a question you would like to ask.

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Michael Fontana

Michael Fontana has been the managing director of telecoms and MSP Optionbox for over a decade and has worked in various telecommunication roles over the last 20 years. Michael has been involved in many exciting projects, such as co-founding telecoms and IT businesses and has now built up a team of more than 15 staff, serving over 300 clients nationwide. With a wealth of experience in IT and a passion for technology, Michael is now helping BTP to produce the highest quality guides on the internet. You can connect with Michael on LinkedIn.

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