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Holds emails with attachments in Outlook outbox

Posted: 04-May-2021 | 7:42PM · Edited: 04-May-2021 | 7:43PM · 51 Replies ·

Don't know if this is an incompatibility with latest ios update or it coincided with a Norton update but emails with attachments were being held in Outlook outbox with error codes of 3253 & 17099. SSL certs were asking to be verified every time Outlook started.

emails without attachments were sending - but a signature with images would prevent the sending - but here was the odd thing - my client had used 32 bit png files in their signature. These had been sending without a problem until the update. Changing those to 8 bit images then let the emails send.

Uninstalled Norton and all was fine again..

With constant VPN pop-up notifications and notices requesting permissions to open apps - Norton has been a total pain on a new MacBook. While seamless integration with PC I won't be reinstalling it on the Mac again.

Labels: Norton Security for Mac, Firewall
Accepted Solution
Kudos0 Stats

Re: Holds emails with attachments in Outlook outbox

Posted: 04-Jun-2021 | 3:13PM · Permalink

Hi,

Thank you for your patience. We have released a hotfix to correct this issue. There won't be a version number change, nor would a reboot be required. Please let us know if this issue persists. Thank you. 

-Gayathri

View Accepted Solution in Context

Replies

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 10-May-2021 | 4:04AM · Permalink

Is there a fix being worked on?

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 10-May-2021 | 10:53AM · Permalink

I am having this same issue using an iMac 27" 2020, macOS Big Sur 11.3.1 and the latest release of Norton 365 Deluxe. I haven't uninstalled Norton to determine if this fixes the problem, however. I'm hoping Symantec fixes it first.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 10-May-2021 | 2:41PM · Permalink

I discovered that the problem goes away when you turn off "Vulnerability Protection".   I tried uninstalling and re-installing and the problem went away for few minutes only.

Hence, the only workaround that I have found so far is to turn off and on "Vulnerability Protection".   I also agree that this problem came up after the most recent update to Norton Security.

Kudos2 Stats

Re: Holds emails with attachments in Outlook outbox

Posted: 10-May-2021 | 11:35PM · Permalink

Thanks for sharing that.

Today I sent a series of test emails:

1) plain email - no enclosures or embedded pictures - RESULT = SENT SUCCESSFULLY

2) email with small attachment (< 5M) - RESULT = FAILED TO SEND (CAUGHT IN OUTBOX)

3) email with embedded small embedded picture - RESULT = FAILED TO SEND (CAUGHT IN OUTBOX)

4) repeat of (1) - RESULT = SENT SUCCESSFULLY

I tried turning off 'Vulnerability Protection' and 2 test emails that had been 'caught' in my Outlook Outbox (2 & 3 above) went immediately. Unfortunately N360 Deluxe crashed a couple of seconds later! 

Incidentally, I tried a similar test yesterday with Apple Mail - absolutely no problems.

I think I'd feel better if I knew that Norton had someone working on investigating this...maybe even collaborating with Microsoft Outlook development team??

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 11-May-2021 | 9:06AM · Permalink

I did further testing:

(1) no attachments; send was successful with vulnerability protection ON

(2) small attachment, tried several types of files, all non-picture/video; send was successful with vulnerability protection ON

(3) small attachment, screen print (.png) file, failure with vulnerability protection ON; success with vulnerability protection OFF

(4) small attachment, movie (.mp4) file, failure with vulnerability protection ON; success with vulnerability protection OFF

I've been working with Microsoft and they keep referring the problem back to a Norton issue. 

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 11-May-2021 | 10:22AM · Permalink

After spending a couple of hours chatting (arguing is more like it) with Norton online chat, they believe it's an Apple issue. I'll humor them a bit and contact Apple Support.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 11-May-2021 | 10:44AM · Permalink

Well done!

I was wondering whether there are some specific set-up firewall needs for Outlook? I'm running 16.50...on Big Sur 11.3.1 and N360 v8.6.3

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 11-May-2021 | 1:30PM · Permalink

Well, after a lengthy and frustrating chat session with Norton, they're now putting the blame on Apple. My ISP blamed Microsoft, who then blamed Norton, and now Apple is in the mix. That will be my next chat - Apple. At least, my past experiences with Apple have been mostly favorable. I'll be back in touch, stay tuned...

BTW, I'm running 16.49 on Outlook, 8.6.3 on Norton 360 Deluxe, Big Sur 11.3.1

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 11-May-2021 | 11:19PM · Permalink

Ah the good old three way blame - at least two months before a resolve will happen when the deny all liability nonsense starts. Even if it is Apple or Microsoft at fault it will be Norton who has to find a solution - they are on the bottom of the heap in this one. 

Meanwhile I could only steer my client to another product.

Kudos1 Stats

Re: Holds emails with attachments in Outlook outbox

Posted: 11-May-2021 | 11:43PM · Permalink

Just woken up to the following response from Microsoft:

"..Recent reports have shown that Norton antivirus is causing this issue and the only solution is to uninstall it. Please follow the steps below for uninstalling..."

...as you said, this is the 3-way blame stage - however, the '3-way co-operation stage'.....could follow!

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 12-May-2021 | 12:42PM · Edited: 12-May-2021 | 1:26PM · Permalink

I have the same issue. Norton 360 is blocking outgoing mail server connections from MS Outlook when the email contains a file attachment, in my case a small PDF file (670 kb). Emails without a file attachment readily go through. Interestingly, I can confirm the emails are transmitted if Norton 360 Firewall Vulnerability Protection is temporarily turned off. This strongly suggests that Norton 360 is the culprit, not Microsoft Outlook or Mac OS. As you say, the problem only cropped up recently (in last 3-4 weeks?). I've tried uninstalling and reinstalling Norton, no effect. Problem simply repeated. Having the same issue on a second machine with different user and email accounts. Sure looks like a Norton bug to me.

Norton Support, stop passing the buck and please fix this.

MacBook Pro13 2020, BigSur 11.3.1, MS Outlook for Mac Vr 16.49, Norton 360 8.6.3

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 12-May-2021 | 2:23PM · Permalink

A lengthy discussion with Apple yesterday and today. Running several scenarios by Apple, sure makes it point to Norton as the problem. But after explaining the runaround we all have been getting from either Norton and Microsoft, the finger pointing towards Apple, Apple has agreed to put me in touch with their engineering team tomorrow on a call to see if we can further discuss and isolate the issue to determine if it's an Apple or Norton or Microsoft issue or something that all 3 need to get their heads around. Maybe something to get the customer uninvolved and them the big boys solve? We'll see.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 13-May-2021 | 2:36PM · Permalink

This is absolutely a Norton issue!  I have spent the last week trying to figure out what happened and was blaming Apple and Microsoft and my ISP provider only to find out that turning off the Norton 360 Firewall Vulnerability Protection finally was the culprit.  I know now that this happened after the last update because it was working fine before. Makes one wonder if Norton is worth it .....this has happened before with software vs Norton.  

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 13-May-2021 | 2:50PM · Permalink

I am having the exact same issue, and wish that Norton would resolve it.  Prior to their latest update, 8.6.3, they were slowing my wired or wireless bandwidth from 480 Mbps down to less than 80 Mbps--so they fixed that issue, and now OutLook (and just OutLook--Apple Mail works fine) can't send attachments.  Hope you get some results from either Apple or Norton, and fast!

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 13-May-2021 | 11:27PM · Permalink

Thanks for this additional info, Gmouse.

Some thoughts for today:

1. Does anyone know how many customers are affected by this? (How many N360 Mac users are also users of MS Outlook?);

2. Does 'the industry' (Norton, Microsoft & Apple in this case) have a process for mature cross-company incident management?

3. Could Norton offer a temporary regression path to the previous version? (in my experience, good developers can always regress...)

MacBook Pro(mid 2015); BigSur 11.3.1; MS Outlook for Mac v16.50 (tried 16.49), Norton 360 8.6.3 (Build 61)

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 14-May-2021 | 1:15AM · Permalink

Re. "2. Does 'the industry' (Norton, Microsoft & Apple in this case) have a process for mature cross-company incident management?" - in my experience when the blame game starts the answer to your question would seem to be "no".

While I estimated 2 months for a fix, I was being conservative - probably three.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 14-May-2021 | 1:19AM · Permalink

Re. "3. Could Norton offer a temporary regression path to the previous version? (in my experience, good developers can always regress...)"
I don't know if this still works
Rolling back Norton Internet Security version
https://community.norton.com/en/forums/rolling-back-nortoron-internety-s...

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 14-May-2021 | 7:56AM · Permalink

Re thought 2:  There is a logical hierarchy here. Mac OS is at the core, Outlook is the first level application and then Norton. That may be functionally inaccurate at the software level, but it is the end user/consumer perspective. In the absence of Norton's software, the Mac OS and MS Outlook are working just fine. It's only when Norton 360 is added to the mix that we have a problem. So, in the end, it doesn't matter if Apple or MS made some underlying change in their software that adversely impacted Norton's product. As the highest level application (or lowest priority), it's still Norton's sole responsibility to make sure their product works with the underlying apps. If not, customers will start looking for a replacement product.

This is pretty simple. The problem is entirely a Norton issue and they need to take ownership of it.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 14-May-2021 | 8:18AM · Edited: 14-May-2021 | 8:20AM · Permalink

Just FYI...I have often, in my previous job as an IT Tech, worked with multiple vendors on problems like this where finger-pointing COULD be an issue.  In the majority of cases, they cooperatively work together to understand the root cause, and then the responsible vendor will take steps to try and resolve the issue.  I have rarely seen otherwise, and this included incidents involving Microsoft & Novell (back when NetWare was King) and more recently, Microsoft and Apple.

Not to say that there's not some finger-pointing going on in this case, but, in my experience, all concerned want to quickly resolve the issue.

I also posted on the Microsoft OutLook For Mac Forum on this issue (https://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_...), so people over there are aware of the cause (in fact there was already a post about an "antivirus" application causing the issue (just didn't state which one), as well as another post mentioning a different antivirus application as being at fault--so, this may very well be a more complex issue caused by interaction with changes made by both Apple & Microsoft.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 14-May-2021 | 9:35AM · Permalink

Something else I have discovered is that the problem to send attachments only occurs when trying to send them from non-Microsoft (Outlook) e-mail accounts (e.g. iCloud, Yahoo, Gmail, etc.).   I guess the problem does not occur when sending attachments using an Exchange account either, but I do not have one to run a test.   In other words, you don't have to turn off "Vulnerability Protection" if you send e-mails with attachments using an Outlook.com account.

I am using Mac OS 11.3.1, MS Outlook 16.49 and Norton for Mac 8.6.3, and I agree, the problems started after the most recent update from Norton.

Hence, I am not trying to leave anybody off the hook here, but it seems like Microsoft and Norton need to work on this as fast as possible.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 17-May-2021 | 4:10AM · Permalink

I'm happy I've found this thread.
Having tried all and I also suspected Norton, but only did extra tests on Outlook that did not help.

Tried the steps above and happy to see mails are being sent ok again. 

Mac OS 11.3.1, Outlook 16.49, Norton 8.6.3

Looking forward to them to solve the issue. 

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 8:50AM · Edited: 21-May-2021 | 8:51AM · Permalink

I have this occurring on 3 Macs. 1 MacBook and 2 iMacs.  all running the following versions.

Mac OS 11.3.1

Outlook 16.4.9

Norton 360 8.6.3

I can send attachments using gmail accounts but no attachments when using comcast accounts. POP or Imap  settings act the same. email with no attachments work fine. Is there any exclusions that can be entered to allow the attachments to work?

Kudos1 Stats

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 9:38AM · Permalink

Dan :

If you don't feel comfortable leaving "Vulnerability Protection" turned off permanently like me until a fix is distributed by Norton, turn it off 5 seconds before hitting the "Send" button and turn it back on when your e-mails w/attachments have left your Outbox.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 11:01AM · Permalink

I have the same problem but switching to ‘New Outlook’ (slider at top right off outlook screen) fixes it it seems.
Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 11:16AM · Edited: 21-May-2021 | 11:23AM · Permalink

JRS2021 That is a good thought but while that would work, the persons that are using outlook are not adept to switching applications just to forward or send an email. I have turned it off for now with a ignore the "fix now" nag screens.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 11:22AM · Edited: 21-May-2021 | 11:23AM · Permalink

TheChief That is very interesting, I hope that Symantic does not decide that that is the "fix" and not fix the real problem. These computers have multiple users and email accounts, I don't want to require new training for the switch to "New Outlook" Plus the warning about folders changing when trying the slider worried the users.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 12:48PM · Permalink

I tried the "New Outlook" as well. However, it doesn't support "On My Computer" folders. It may be a workaround for users who don't store/archive mail on their computer, but it isn't an option for me.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 1:07PM · Permalink

KB22 Not supporting "On My Computer" folders is the main reason that I cannot use the "New Outlook"

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Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 3:03PM · Permalink

Agree, until the "new" OutLook for Mac supports everything, I can't use it.  Also, does anyone know if there are multiple Norton Support tickets open on this issue?  I know in past Norton wouldn't work on any issues without a LOT of tickets opened.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 21-May-2021 | 4:06PM · Permalink

Gmouse good thinking...I just opened another ticket.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 22-May-2021 | 6:51AM · Permalink

I have the same problem
It's a real shame for a paid service.

Does anyone have any information on the development of a solution

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 29-May-2021 | 9:28AM · Permalink

hello,

Has anyone tried with OS 11.4

Is the problem solved?

Thanks

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 29-May-2021 | 9:50AM · Permalink

OS 11.4 does NOT fix the problem. (at least with comcast.net email accounts).

I have tested this on both intel and apple M1 systems.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 29-May-2021 | 1:17PM · Permalink

Same here. No change with OS 11.4. Emails with attachments still don't go thru unless Norton Vulnerability Protects is turned off.

Plain text emails are fine.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 30-May-2021 | 7:04AM · Permalink

Hello everyone,

thank you for your feedback

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 31-May-2021 | 7:09AM · Permalink

Just got upgraded to Norton 360 8.6.4 Build 54.  This did NOT fix the problem with Microsoft OutLook being able to send files with attachments.  Still have to turn off Vulnerability Protection to send.  Really wish these guys would get it together on fixing this issue!

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 31-May-2021 | 9:13AM · Edited: 31-May-2021 | 9:19AM · Permalink

Concur. I've been on Norton 360 8.6.4 Build 54 for a few days. All the software on my MacBook Pro is up to date: Mac OS 11.4, Outlook 16.49 (MS 365).

No resolution to the problem...

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 31-May-2021 | 10:17AM · Permalink

I concur too. No improvement.

What makes it even more difficult is the lack of PROBLEM OWNERSHIP, OPENNESS and PROGRESS.....how do we know anyone is listening in Nortonland?

I'm sure those who contribute to technical forums, both want a fix - and are prepared to help, too. Please, Norton, would you show some leadership here?

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 01-Jun-2021 | 2:39AM · Permalink

Hi,

We apologise for the inconvenience caused. This is being looked into as a high priority issue. We request you to kindly be patient until we determine a fix for this issue. Thank you for posting on the Norton Community. Once I have an update, I will share it in this forum thread. Thank you. 

-Gayathri 

Gayathri R | Norton Forums Global Community Administrator | NortonLifeLock
Kudos1 Stats

Re: Holds emails with attachments in Outlook outbox

Posted: 01-Jun-2021 | 3:58AM · Permalink

Dear Gayathri,

Thank you very much for your response and for the information that this is being looked into as a high priority issue. I'm sure all interested parties would find it useful to have updates as a fix is developed. If the development team would like us to do testing - all you have to do is ask...

Many thanks

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 03-Jun-2021 | 11:26AM · Edited: 03-Jun-2021 | 11:26AM · Permalink

I am noticing a continuing issue similar to that of 8.6.3 on Big Sur (wired or wireless connectivity was tremendously slow, in my case dropping from 480 Mbps to ~80 Mbps).  While that exact issue seemed fixed with 8.6.4, which brought the issue we are all having with OutLook, I am seeing tremendous slowdowns in CERTAIN things, such as Apple Maps taking a VERY long time to download things, especially if you are in Satellite view and Apple TV App taking a long time to fill in image blocks when going over lists of new shows.  If you turn off Norton, these issues vanish.  SpeedTest shows me getting 480 Mbps download speeds, but seems like some kind of throttling is still going on at least with certain applications.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 03-Jun-2021 | 4:51PM · Permalink

Gmouse There is another thread about the speed problem. I am following that one too as I have the same issues.

Zero help from Norton fixing slow down from 1 GB to 50 megs

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 04-Jun-2021 | 11:33AM · Permalink

Hi !

Something changed from yesterday to today because I no longer have problems sending e-mails w/attachments with "Vulnerability Protection" being active.  I am on Mac OS Big Sur 11.4 since last week, Norton Security for Mac 8.6.4 Build 54 also since last week, and MS Outlook 16.49 (21050901) since at least 3 weeks.

The problem seems to be gone since this morning with no apparent updates.   I will continue to monitor and report to this group.

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 04-Jun-2021 | 11:52AM · Permalink

Agree, JRS2021, I was able to send email with an attachment just now.  I know that Microsoft AutoUpdate updated Edge for me yesterday and my first thought was OutLook got updated, but you're right, I have the same version and file is dated 5/11/2021.  Soooo...since the main Norton app/OutLook/macOS Big Sur versions didn't just changed...what DID change, or was this something via LiveUpdate?

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 04-Jun-2021 | 12:00PM · Permalink

JRS2021:

You are correct. I too am now able to send emails with attachments. Specs: Mac OS 11.4, Norton Security 360 8.6.4 Build 54 and MS Outlook for Mac 16.49. (21050901). However, looking at my Norton security history I see a couple updates that may explain why it is now working. Norton Vulnerabilty Protection for Mac updated yesterday evening (Jun 3) and Norton Security for Mac updated this AM (Jun 4th).

Hopefully this will resolve the issue permanently. 

Accepted Solution
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Re: Holds emails with attachments in Outlook outbox

Posted: 04-Jun-2021 | 3:13PM · Permalink

Hi,

Thank you for your patience. We have released a hotfix to correct this issue. There won't be a version number change, nor would a reboot be required. Please let us know if this issue persists. Thank you. 

-Gayathri

Gayathri R | Norton Forums Global Community Administrator | NortonLifeLock
Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 04-Jun-2021 | 4:03PM · Permalink

I have tested the updates on two systems and can confirm that the fix works. Outlook emails with attachments are now working!

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 05-Jun-2021 | 12:06AM · Permalink

Like others, I have tested this fix. In my case:

Attachments: Word, PPT & pdf

Using MS Outlook 16.51 (pre-general release version)

All great now - thank you Norton!

CONTINUOUS IMPROVEMENT CHALLENGE TO NORTON: "What have you learnt from this episode in (a) handling customers; and (b) reaching faster fixes ??"

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 28-Jun-2021 | 11:07AM · Permalink

How do you download the hotfix?

Kudos0

Re: Holds emails with attachments in Outlook outbox

Posted: 28-Jun-2021 | 11:45AM · Edited: 28-Jun-2021 | 11:59AM · Permalink

ilcajun, You can just perform a live update, The current version is 8.6.4

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