Outlook Web App Not Attaching Files On Mac

  1. Outlook Attach Button Not Working
  2. Outlook Web App Will Not Attach Files

I’m using Google Chrome as my default browser but after installing the latest update of Chrome, I find several features within Outlook Web App (OWA) to be no longer functioning.

Jul 24, 2019  New Attach File menu in Outlook 2016 with a Recent Items list and options to insert or link to files from Cloud Storage locations. Controlling what is stored in Recent Items The Recent Items list is being fed from the Recent Items or Quick Access list that Windows maintains and there is hardly a way to control it other than editing the Recent.

Some of these features are:

  • Opening the Address Book (either via the icon or pressing on To, CC or BCC).
  • Attaching files.
  • Inserting pictures.
  • Typed hyperlinks duplicate after hitting spacebar or enter.

Is there any way to fix this?

As of Chrome 37, the “showModalDialog” API has been deprecated by the Chrome development team and completely removed as of Chrome version 42.

Until April 30, 2015, a Registry modification allowed you to re-enable the API for Chrome versions 37 to 41.

If your administrator keeps the Exchange servers up-to-date, you should no longer have this issue. Installing Silverlight, could otherwise solve some issues as well.

The duplicate hyperlink issue in OWA 2010 is a separate bug of Chrome (introduced in version 37) which the Chrome development team is looking into.

OWA 2010 users and OWA 2013 admins mostly affected

Before the latest Exchange updates, OWA 2010 used the “showModalDialog” method quite a bit for various user features which are mentioned above. OWA 2013 used it a lot less in the client environment and the aforementioned features did not break in OWA 2013.

However, OWA 2013 did use this method quite a bit in the Exchange Administration Center (EAC or where your OWA URL ends with /ecp). For instance, when trying to manage the email addresses of an account, you couldn’t add an alias to the account as pressing on the + icon did nothing. This also applied to various other dialogs which only required a single input of data like when managing the network adapter bindings when creating/managing a Receive Connector.

Workarounds and temporary Registry fix

While you could use another browser (just for OWA) for the time being, this might actually not be that easy within a corporate environment. It might be easier to switch when you are an Exchange administrator and otherwise you can still do things via PowerShell.

A quick fix for the attachments issue is to install Microsoft Silverlight. This can be deployed in a corporate environment and might already have been installed for you. It gives you the added benefit of being able to continue to type your message while the attachments are being uploaded.

A solutions that worked until April 30, 2015 was to re-enable the showModalDialog API via the Registry.

Not

Key: HKEY_CURRENT_USERSoftwarePoliciesGoogleChromeEnableDeprecatedWebPlatformFeatures
Value name: 1
Value type: REG_SZ
Value: ShowModalDialog_EffectiveUntil20150430

To apply this change without needing to go into the Registry yourself, use the reg-file from the downloadable zip-file below.
Download: chrome-showmodaldialog.zip


OWA in Chrome 37 and later could temporarily be fixed with a Registry key.
(click on image to enlarge)

Note for Enterprise administrators
You can also manage this setting and other settings via Group Policy by downloading the Chrome Policy Templates.

The setting “Enable deprecated web platform features” can be found in both the Computer Configuration and the Use Configuration policy tree:
Administrative TemplatesGoogleGoogle Chrome

OWA fix in Exchange Cumulative Updates

As the Exchange Team intends to fully support Google Chrome as a browser for OWA, installing the latest Rollup Update for Exchange 2010 or the latest Cumulative Update for Exchange 2013 also solves the aforementioned issues.

Any issues in OWA 2007 and previous caused by the latest version of Chrome will not be addressed as they are out of mainstream support and never officially supported Chrome anyway.

Modifying this control will update this page automatically

Mail User Guide

You can include photos, documents, and more when you write messages.

When you attach images or PDF documents, you can mark them up in Mail before you send your message.

Include photos and other files in emails

In the Mail app on your Mac, do any of the following:

  • Click the Attach button in the toolbar, locate a file (you may need to click the sidebar button to see additional folders), select it, then click Choose File.

    You can also drag files from the desktop, the Finder, or an app into your message.

  • For photos, click the Photo Browser button in the toolbar, then drag a photo into your message. You can also take a photo or scan documents, or add a sketch, using your nearby iPhone or iPad.

By default, Mail inserts images at their actual size. If different sizes are available, you can choose one from the pop-up menu located on the right side of the message header.

Send large email attachments using Mail Drop

Outlook Attach Button Not Working

You can use Mail Drop to send files that exceed the maximum size allowed by your email account provider. Mail Drop uploads large attachments to iCloud, where they’re encrypted and stored for up to 30 days.

  • If you have an iCloud account and you’re signed in to iCloud when you click Send, Mail automatically sends the attachments using Mail Drop. Mail Drop attachments don’t count against your iCloud storage.

  • If you don’t have an iCloud account, or if you’re not signed in, Mail asks you whether to use Mail Drop (to always use Mail Drop select “Don’t ask again for this account”).

If a recipient uses Mail in OS X 10.10 or later, the attachments are included in your message. For other recipients, your message includes links for downloading the attachments, and their expiration date.

You can turn Mail Drop on or off for an account. Choose Mail > Preferences, click Accounts, select the account, click Advanced, then select or deselect “Send large attachments with Mail Drop.”

See the Apple Support article Mail Drop limits.

Put email attachments at the end of messages

In the Mail app on your Mac, do one of the following:

  • For the current message: Choose Edit > Attachments > Insert Attachments at End of Message.

  • For all messages: From the Message viewer, choose Edit > Attachments > Always Insert Attachments at End of Message (a checkmark shows it’s on).

Include or exclude email attachments in replies

In the Mail app on your Mac, do one of the following:

AttachAttach
  • Include or exclude original attachments in a reply: In the toolbar of the message window, click the Include Attachment button or the Exclude Attachment button .

  • Include or exclude original attachments in all replies: From the Message viewer, choose Edit > Attachments > Include Original Attachments in Reply (a checkmark shows it’s on). To turn it off and exclude attachments, choose the command again (the checkmark is removed).

Send email attachments to Windows users

In the Mail app on your Mac, try these suggestions:

  • Send Windows-friendly attachments. To do so for all messages, choose Edit > Attachments, then select Always Send Windows-Friendly Attachments. For a specific message, click the Attach button in the toolbar of the new message window, then select Send Windows-Friendly Attachments (if you don’t see the checkbox, click Options in the bottom corner).

  • Send documents as PDFs instead of in their original format.

  • Use filename extensions (such as .docx for a Microsoft Word document).

  • If the recipient sees two attachments (such as “MyFile” and “._MyFile”), the recipient can ignore the file with the underscore (such as “._MyFile”).

To display an attachment (such as a one-page PDF document or an image) as an icon, Control-click the attachment in your message, then choose View as Icon. To show the attachment again, Control-click it, then choose View in Place.

If the message size shown on the left side of the message header is red, the attachments are causing your message to exceed size limits set by your email account provider. Try reducing the number or size of attachments or use Mail Drop.

Outlook Web App Will Not Attach Files

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