Problem with Outlook 2013 Attachments

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Senior Member
Outlook version
Outlook 2013 32 bit
Email Account
I recently have been having issues with attachments in Office 2013 on my Desktop computer running Windows 8.1. The first is with receiving messages that contain PDF attachments. I get the message “Adobe Reader could not open the file because it is either not a supported file type or the file is damaged”. Even if I save the attachment to my computer and try opening, I get the same error message. Anyone who e-mails me a PDF document, I’m getting this same error message.

My Outlook e-mail is associated with my Gmail account. If I log onto my Gmail account and open this same e-mail message, I am able to open the PDF document, so I know the PDF file is good.

A related issue is that whenever I send an e-mail message with an attachment (not just PDF file), the message remains in my Outbox and never gets sent. When I click on the “Send/Receive”, to see the progress, it shows the error “Cannot connect to the network (0x800CCC13)”. I know for a fact I’m connected to the Internet, so this error is not accurate.

Thinking Outlook 2013 has gotten corrupted I did an Office “Quick Repair”, as well as an “Online Repair”, but that did not resolve the issue. I’ve also run “Scanpst.exe” to repair any errors with my PST file. I also created a new Outlook profile. I’m running Office 2013 (v15.0.4693.1002).

I did a further test. I logged onto my AOL account and sent a message to my Gmail account with a JPG attachment. The message was received to my Gmail account, but it did not show up in my Outlook Inbox. The Outlook status bar continuously shows “SYNCHRONIZING ‘Inbox’, but nothing shows up in my “Inbox”.

I closed and restarted Outlook and the message still has not appeared in my “Inbox”. I have been receiving other e-mail messages to my Gmail “Inbox” account, but they are not appearing in my Outlook “Inbox”. It’s as if this one message with the JPG attachment is holding up all my other inbound messages. I logged back into my Gmail account and deleted the message in my Inbox with the JPG attachment and 2 new messages appeared in my Outlook “Inbox”.

Finally, I have a Surface 2 tablet running Outlook and I am able to open the PDF document attached to the e-mail message giving me problems on my desktop computer. I suspect something is wrong with the Outlook on my desktop computer.

I’m looking for some advice as to how to resolve my issue. Do I have to uninstall and re-install Outlook or is there some other less drastic steps I can take to resolve my issue?
If you start Outlook in safe mode, can you open the PDF? Issues like this are often caused by addins, usually installed by antivirus programs.

To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.
[DOUBLEPOST=1426628245][/DOUBLEPOST]Also, does it work if you open outlook using run as administrator?

Started Outlook in Safe mode and problem persisted.

Ran Outlook as Administrator and there was a warning that there was a problem with an Add-in from "CompanionLink Outlook Add-In". It wasn't disabled because it's in the "Always enable" list. I clicked on the button to disable it. Still got the Adobe PDF error when I tried to open the attachment. I closed Outlook and started again as Administrator. Problem still persists. I tried sending a message with a JPG file attached and the message still gets stuck in the "Outbox".

There were two other add-ins, but it said they were already disabled - IVT BlueSoleil Outlook Add-In and TeamViewer Meeting Add-In. I'm not aware that I am using either of these two.

Any other suggestions?

team viewer addin adds meetings scheduled in team viewer to your calendar. bluesoleil is a Bluetooth/phone manager.

Is onenote addin enabled? do the messages send if you don't look in the outbox?

Have you repaired the office install?

The onenote is currently active. These are the other add-ins that are active - iCloud Outlook, MS Exchange, MS VBA, Outlook Social Connector 2013 and Redemption Helper Outlook Extension. I unchecked all of the "Active" add-ins, closed Outlook and then restarted Outlook. The problems persisted. I went back and re-checked all those that I had previously unchecked.

Yes - I did an Office “Quick Repair”, as well as an “Online Repair”, but that did not resolve the issue.

I sent a new test message and attached a different jpg file (14 KB) and waited about 2 minutes before looking in the "Outbox" and the message was no longer stuck in the "Outbox". However, the message did not appear in the "Sent Mail" folder. The Outlook Status bar continuously shows SYNCHRONIZING 'Sent Mail'. This has also been a symptom of my issue. Normally if I click on another Outlook folder (e.g. Inbox), the status bar changes to the new folder and momentarily syncs, but in this case it is continually showing SYNCHRONIZING 'Sent Mail'.

I closed and restarted Outlook to see if the message would appear in the 'Sent Mail' folder. The status bar shows the SEND/RECEIVE progress bar; "ALL FOLDERS ARE UP TO DATE" and "Trying to Connect", which after a minute changed to "CONNECTED". The message appeared in the "Sent Mail" folder. The Outlook Status bar is showing SYNCHRONIZING 'Sent Mail'. I was able to switch between Outlook folder and what ever folder I select, it briefly displays the SYNCHRONIZING status, but when I select the 'Sent Mail' folder it keeps displaying the SYNCHRONIZING status. I'm guessing if I had not closed and restarted Outlook, that message I sent would never appear in the 'Sent Mail' folder.

I decided to try sending different size 'jpg' files (2 MB, 1 MB, 256 KB) thinking it might be an attachment size issue, but each time waited 5 minutes and the messages never left the 'Outbox" folder. Outlook Status bar will periodically display "Sending Message 1 of 1". I end up deleting these messages from the "Outbox".

Not sure why the first message made it out of the "Outbox" and the next 3 attempts didn't.

One other anomaly. Don't know if this is related to my issue or not. When my wife e-mails me a meeting request, it appears in my "Inbox". I accept the meeting, but do not send a reply. The meeting appears on my Google Calendar, but not on my Outlook Calendar. My calendar is synched through and when I log into, the meeting does not appear on that calendar either. I use to synch my Outlook Calendar, People and Tasks between my Outlook running on my Desktop and Surface 2 Tablet. I have no issue with my Outlook running on my Surface 2 Tablet.
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