This topic

Emails stuck in Outbox-can this be IP Address related?

Psych13 — Tue, 01 Aug 2023 20:23:47 GMT

Over the last few days, when I try and send an email it gets stuck in the Outbox. Having spent nearly an hour on the phone with Apple troubleshooting, they were confident this is an issue to do with BT's mail servers, and not an Outlook issue as I had originally thought. I am open to any explanation though.

A few things to note:

I use Outlook for Mac (I have a Macbook Air-OS is Ventura 13.4.1), but tested this (to try and replicate the issue) using the Mail App on my Macbook Air-and the same issue arose.
This does not happen when I use the BT web based mail.
I noticed that the IP address that is associated with the BT mail error message (screenshot on the right-below), matches the one that comes up when I Google "What is my IP address" but the IP address that I see in System Settings...Network...Wifi....under my broadband provider....(screenshot on left) is different. My broadband provider is not BT-it's Hyperoptic.
So, when I spotted the difference in IP addresses between the one that Outlook recognises, and the one that my Internet Service Provider seems to think it is....I decided to turn my VPN on-I never use my VPN unless I'm travelling. And voila! Turning the VPN "on" rectified the issue. I can send emails when my VPN is turned on.
So I'm wondering what does this mean? Does turning the VPN on mean that the IP address associated with the VPN....overrides the IP addresses that Outlook and my broadband company recognise, making my IP address consistent across Outlook & my broadband company? And if so, does that suggest this is an IP address issue?
Also, of interest, the problem sending emails does not happen when I use my old laptop-also a Macbook Air-but an older OS: Mojave. Same email settings, etc. But I don't have problems sending emails. Why is that? I've had my new laptop for a few weeks and this issue is only *days* old, so I don't think it's because my laptop is new/newer OS, but oddly, I don't have "sending" problems on my old Macbook Air.

I'm trying to understand the source of the issue, i.e., what is stopping my emails from sending-when my VPN is *off*/disabled? In other words, when I'm at home, and using my home internet connection, and Outlook for Mac...why is my email not sending?

I'm attaching the error message that comes up in Outlook when I try and send...I have blacked out my email address as well as the IP address. I'm also attaching a screenshot of my Network Settings on my laptop-IP address is blacked out, but please note that the IP address in my Network settings on my laptop (associated with the broadband provider) is not the same IP address that comes up when I check it here: www.whatismyipaddress.com

I am 100% the username and password for my BT Mail are fine-that is not the issue.

And also note, as I've said above...the IP address that comes up when I check on that site....is the same one that comes up in the BT Mail error message in Outlook.

And to repeat: when I turn my VPN *on* this resolves the issue and my emails send just fine from Outlook for Mac.

What is all this about? This is a relatively new/recent problem.

If anybody else has a clue as to what may be going on-please share your thoughts with me.

I shouldn't have to use a VPN in order to send emails.

Many thanks.

Re: Emails stuck in Outbox-can this be IP Address related?

licquorice — Tue, 01 Aug 2023 20:29:08 GMT

Are you paying £7.50/m for premium mail?

If not, your mail has been downgraded to Basic mail which is only available via webmail, hence your problem.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Tue, 01 Aug 2023 20:31:23 GMT

I am paying for Premium email. And the problem only occurs when sending-not when receiving. If it were to do with being downgraded, presumably I would not be able to receive either. But to be clear-I pay for Premium email.

Re: Emails stuck in Outbox-can this be IP Address related?

gg30340 — Tue, 01 Aug 2023 20:36:49 GMT

Just to clarify... Are you presently a BT Broadband customer or are you paying for a BT Premium email account?

Have you checked that you are using the correct settings for BTMail as per this link

BT Email server settings | BT Help

If you are not a BT Broadband customer or using a BT Premium email account your BTMail account will have been downgraded to a "Basic" BTMail account. This can only be used via webmail and can not be used with an email client.

You should be able to check if you log onto your MyBT and go to "your products" > manage then "Email" > manage then check the "Account Type" at the top of the page.

EDIT: Post crossed with the above messages but still worth checking in your MyBT.

Re: Emails stuck in Outbox-can this be IP Address related?

licquorice — Tue, 01 Aug 2023 20:42:55 GMT

@Psych13 wrote:

I am paying for Premium email. And the problem only occurs when sending-not when receiving. If it were to do with being downgraded, presumably I would not be able to receive either.

Not necessarily, there have been a few cases lately where folks on Basic mail could receive but not send. I guess they update the SMTP servers at different times to the IMAP servers.

By connecting via a VPN (therefore different IP address) you are probably accessing a different server within the farm. Either the server you are connecting to directly has wrongly configured your account as Basic or, more likely, just faulty.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Tue, 01 Aug 2023 20:48:18 GMT

Thanks for this, but to be clear: I am a BT Premium email customer, and as such, I can still use my btinternet.com addresses/accounts in email apps in addition to the web based mail. I am no longer a BT broadband customer-their speed wasn't fast enough in my area and I had to move providers. But this was *years* ago and has nothing to do with my current email issues. I'll check my BT mail settings tomorrow, just to be sure but I'm quite certain they are correct-as I said, I have two laptops-one at my office and one at home. Same BT email settings, but only laptop at home has the issue.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Tue, 01 Aug 2023 20:46:06 GMT

Thanks for this, Licquorice-so is there anything BT can do to resolve this for me re: "Either the server you are connecting to directly has wrongly configured your account as Basic or, more likely, just faulty".

Re: Emails stuck in Outbox-can this be IP Address related?

gg30340 — Tue, 01 Aug 2023 20:47:59 GMT

Did you check your MyBT as suggested?

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Tue, 01 Aug 2023 21:10:42 GMT

I'm 100% certain I have Premium email-I pay £7.50/month and I can read my Account Type as Premium email.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Tue, 01 Aug 2023 21:14:58 GMT

Yes:). I think you're focusing on insignificant details-I am a Premium Email customer, I can send/receive using my BT Mail App, I can also send/receive using Outlook on my old laptop-which is at work, and incidentally, I have a BT Business broadband account at work . I *cannot* however send emails from my laptop at home-where broadband provider is Hyperoptic, and as per my original message-I am convinced this is something to do with an IP address not being recognised.

Re: Emails stuck in Outbox-can this be IP Address related?

licquorice — Tue, 01 Aug 2023 21:33:14 GMT

Its not an insignificant detail, its a means of establishing which of the 2 scenarios I posited earlier is the problem and how to go about resolving it.

If your account is showing as Premium mail, it would appear the problem lies with the particular server you are connecting to. Have you tried disconnecting your line for half an hour or so to obtain a different IP address and see if that resolves things? If not, try it.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Wed, 02 Aug 2023 06:44:32 GMT

Thank you, Licquorice-I understand that you were trying to ascertain what the problem is, but I think I replied in more than one reply that I *am* a BT Premium customer & it felt to me that we were covering basics unnecessarily. But I hear you:).

When you suggest disconnecting my line-do you mean my router? My phone line? I'm not quite sure what you mean.

I have a feeling that BT (server)? seems to think my IP address is something it isn't, but my confusion is over the fact that the IP Address that "What's My IP Address" brings up...*is* the same one as what the BT error message quotes too. The IP Address that is different is the one associated with my broadband provider/router.

I'm going to phone BT Premium Mail later and may also try and speak to my internet/broadband provider again-though when I first spoke to them-they pointed me in the direction of BT.

Re: Emails stuck in Outbox-can this be IP Address related?

licquorice — Wed, 02 Aug 2023 07:17:39 GMT

I realise that you have stated numerous times that you are a Premium Mail customer, the point we were trying to ascertain is do BT's systems agree with that assertion or have you inadvertently been downgraded without your knowledge. Checking in MyBT would verify that.

I had forgotten you were an Hyperopic customer rather than BT so the disconnect scenario isn't relevant.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Wed, 02 Aug 2023 07:33:53 GMT

Thank you, and I hear you. BT's systems definitely agree with it. I've just spoken to BT Premium Mail and they suggested as a first step, that I take my laptop to work, to test out my server/network outside the home, and try and connect to my broadband at work (which happens to be BT Business). I'll do that this afternoon and will report back.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Wed, 02 Aug 2023 10:17:47 GMT

Very quick update: I spoke with Hyperoptic and they helped me discover that my public IP address had been blacklisted. They reset my IP address to a new one and all is working fine! Thank god for that. Thank you to all who took the time to reply to my post. Something that I learned about public IP addresses is that we all share our public IP addresses with a lot of different users, and if somebody else misuses internet…our own IP address can become blacklisted. These people can be anywhere in the world. Hyperoptic offer a static IP address for an extra £5/month-that means it's mine, and mine alone. I am not opting in just yet, but if I have this issue again I would definitely consider a static IP address.

Re: Emails stuck in Outbox-can this be IP Address related?

licquorice — Wed, 02 Aug 2023 10:20:31 GMT

Thanks for the update, glad an IP address change sorted it.

Re: Emails stuck in Outbox-can this be IP Address related?

Psych13 — Wed, 02 Aug 2023 10:29:00 GMT

Thanks very much:).

Re: Emails stuck in Outbox-can this be IP Address related?

gg30340 — Wed, 02 Aug 2023 10:45:10 GMT

In the event that it does happen again, before opting for a static IP address try try turning your router off for about half an hour and when you turn it back on your ISP will probably have issued you with a new IP address that hopefully will not be blacklisted.