Problem:

Office 365 Outlook Attachment Problems Today
Outlook 365 Attachment Issues

This is a strange one and seems like it must be an Office 2016/Office 365 issue as I 've received two reports from different customers in the past 24 hours. Firstly this problem only seems to occur when a third party application generates a new email in Outlook, one customer is using s Fujitsu ScanSnap scanner, the other an application called. These issues tend to manifest more frequently in previous versions of Microsoft Office such as Office 2010. If it’s an option, the simplest way to avoid these issues in the future is upgrading to Office 365. On top of avoiding file version errors, Office 365 comes with built in features that can read documents aloud like Narrator, transcribe. If the tool doesn't resolve the issue, go to Windows or Look to start Microsoft Support and Recovery Assistant for Office 365 (SaRA). On the first screen, select Outlook, and then select Next. Select any of the following options, as appropriate, and then select Next: Outlook keeps hanging or freezing.

Outlook for Office 365 Bug Fix Update for June 2020. A Bug Fix update has been released for Outlook for Microsoft 365 ( Current Channel) and it comes with 7 highlighted fixes for Outlook and another 7 for other Office Apps that are part of Microsoft 365. The following issues have been resolved in Outlook; Addressed an issue where Outlook failed.
I never had the this problem with the original Outlook for Mac 2011, just with the updated Version 15. I have a gmail account, gmail business account and hosted exchange account. It does not matter which account I send from, I experience the same problem. I'd say it occurs 90% of the time I am sending an email with attachment.

You experience various problems with images in email signatures, e.g. embedded pictures are not displayed in received emails, are misplaced in the message thread, or disappear when replying/forwarding.

Solution:

Embedded images are images that are inserted directly into the body of the message, as opposed to images that are attached as separate files or inserted as links. CodeTwo software allows you to embed images in email signatures and in most cases such images are better than linked images (learn more). Occasionally, embedded images may not appear correctly. For example, if images are suddenly gone from a conversation thread, it usually means the email was either converted to a different format (e.g. from HTML to RTF) or processed in a way that removed or misplaced images. This article describes the most common problems with signature images and explains how to fix them. The problems are divided into several categories and the most common problems are listed first.

Frequent problems

Problems related to email client restrictions

Problems related to undesired format conversion

Issues that occur on Apple devices, mobile devices and web-based mail clients

Problems related to the image itself

Other problems

Frequent problems

Problem: Images are not displayed or you get security warnings when opening emails with CodeTwo signatures.
Solution: Did you insert the image from a web location into your signature? Storing pictures online is a good way of reducing email size, but it comes with several disadvantages. If your recipients have limited Internet access or no Internet connection at all, their email clients will not be able to download images from the external web locations. Furthermore, many email clients (including webmails) come with security features that prevent against automatic downloading of external content linked in emails. If your signature contains images stored in a web location, email recipients may see security warnings. Similar behavior occurs if your email includes embedded images which are also hyperlinked.

In many cases, embedding images into email signatures can be a better solution. Learn why

Problem: Images are visible in the original message but disappear from replies or forwards.
Solution: This issue is most probably caused by email client settings. An email client may be configured to always reply using a specific message format, regardless of the original format. If such format conversion occurs, it can cause problems with disappearing images, images visible as attachments, CID placeholders or picture names showing up in the message body instead of images. Similar conversion may happen on the intermediary mail servers as well. To mitigate this problem, you can tell your users about it and ask them to change their mail client settings, if possible. If you're working in an Exchange environment, you can force the HTML email format in Exchange. Some other workarounds may be available, for example some iOS versions remove images when replying but keep images when forwarding emails, so forwarding instead of replying may be an option to keep images in place.

Problem: Images are visible in the original message but disappear or suffer quality loss with every reply.
Solution: This problem might be related to unwanted email conversion by email clients, especially in long conversation threads. Go to this section for details.

Problem: Images embedded in email signatures created in Outlook are not visible to recipients.
Solution: If you experience problems with native Outlook signatures, see this section.

Problems related to email client restrictions

Images are not displayed (and you need to download them) or are sent as attachments

This may be caused by email client security restrictions and/or bandwidth usage protection. If an email contains a linked image, your email client might show a red x in a box () icon (Fig. 1.) or an empty picture frame instead or show no linked content at all.

Fig. 1. External content is blocked by Outlook.

To solve this issue, you can use one or more of the solutions provided below:

If security restrictions are used, you can change the email client settings to enable downloading remote content from the Internet. This can be done directly in the affected message or you can configure how images are handled in all emails using your email client’s settings. Below are links to instructions on how to do this in some email clients:

Info

Most email clients do not automatically download images from external servers because information gathered while opening remote resources (such as websites) may be used by their owners to identify visitors.

However, owners of remote servers containing the images are only able to obtain your IP address and information on the mail client you used to download the images. There is no option to gather any credentials used for authentication on the mail servers.

If bandwidth restrictions are in place, you can modify the email signature and the graphics used in it by:
- limiting the number of images in the signature,
- reducing the size of graphic elements in the signature by using lower-resolution images,
- using different image file types, especially those that allow for lossy compression that reduces the file size e.g. JPG (JPEG), instead of files with lossless compression e.g. PNG or BMP.

To avoid bandwidth restrictions, you can configure your CodeTwo email signature solution to only add a signature to the first message in a conversation by selecting the Add the [signature] to the first email only (do not add it to subsequent emails) option or to remove your previous signatures from a conversation when a new message is sent by selecting the Add the [signature] to every email but remove its previous occurrences in an email conversation option.

Follow the links below to find out where you can find these options when using:

Problems related to undesired format conversion

Default email format and its conversion in email clients

Every mail client can use a different default message composing format. Depending on the platform, you can send your message in HTML, RT

Office 365 Outlook Attachment Problems