Yahoo Mail Apple Mail OSX 10.13 SOLVED, probably

HELP!
Very close to putting a brick through this effing iMac

Out of the blue this morning I gets a message asking me to re-enter password for one of the two yahoo mail accounts I have on OSMail on the mac. When I try to do so I get a IM

"Connection insecure Failed to verify the server certificate. This could be because of your network configuration or your proxy settings."

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Having searched that IM into various mac support forums perceived wisdom points towards outdated or invalid certificate. Opened keychain and deleted all certs with a wee red box. Reboot mac, reboot mail. still get the IM. Other suggestion was to remove antivirus....I do not have, never have had any antivirus.
Deleted the offending yahoo mail account and I cant add it back, just get IM again.
I am not using a VPN.
The offending account works fine on Samsung phone and iPad
I said I have two yahoo accounts . The other works fine.

Must be a iMac issue but what and where?

Got to go out to clear my head any bright ideas gratefully received and will be acted upon my return.

I'm afraid I've got no idea. But I have only ever used web base gmail.

In desperation I spoke to Apple support.
The security of the mail client cannot be matched with the security of the ageing operating system.
I can’t upgrade the OS so I’m stuffed.
Mac is late 2009 and due for replacement. I’ve been thinking about replacing it for a while but at the moment ICBA. Birthday next month

Just had a thought..
Supposin I installed a different mail app on the iMac , might that get around the problem?

Andyp":12kropmh said:

Just had a thought..
Supposin I installed a different mail app on the iMac , might that get around the problem?

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Yep could do.

TrimTheKing":2xryrz9k said:

Andyp":2xryrz9k said:

Just had a thought..
Supposin I installed a different mail app on the iMac , might that get around the problem?

Click to expand...

Yep could do.

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tried thunderbird. Looks awful abandoned when I couldn't get my yahoo contacts added and mailboxes would not merge into one inbox.

I really am stuffed IF we want to work as was with the apple Mail app.

Grrrr :evil: :twisted:

All too much to get my head around at the moment.

I have less and less confidence in Apple code as the days pass. It must be the most horrible spaghetti behind the scenes.

SWMBO uses an iPad for almost all of her work (but with a keyboard), and recently it stopped connecting to my Laserjet directly because of "security certificates".

I'm not spending 300+ quid on a replacement network card for the printer, when even that might not fix the issue. I re-routed her via my desktop PC (which has a couple of print queues available on it). That worked for a while, then it started demanding US letter paper, so I hacked the PPD so as to tell the iPad it could NOT have US Letter (nor Legal, nor A5, etc.).

Guess what: that worked for a while, too, then it refused to print in landscape (hacked PPD again), then the default no. of copies became infinite (apparently). After about 27-or-so pages wasted, twice, she thought to mention it over dinner... And before anyone says anything I am aware of the syntax of a PPD file!

This entire problem was instigated by Apple. I have a "sticking-plaster" plan, if that fails that I will ceremoniously drop the thing from the top floor onto the patio, and have a wild party before buying her a Samsung tablet...

Similar issues with both our 2020 iPhone SEs, coupled with battery life of less than one day (all background processes possible turned off). It's also developed a phantom alarm setting, about 90 minutes before normal (grrr), which doesn't show up in the list of alarm times, so apparently cannot be deleted.

And the latest 'software update' offered me extra emojis. I have refused it, and the sky hasn't yet fallen in, but I cannot stop it nagging me.

Have you ever noticed that the information about any Apple "software update" never includes any detail about bugs found and supposedly fixed? Nor can you opt only for bug fixes and not so-called improvements.

Time was, when the kids were still at home, we ran three or four desktop Macs (I was the only one in the house with a Windows PC (a laptop for work). Even the family Quake server was Linux. I recommended Macs as they were so easy to network and file share with Samba - everything just worked.

Not so any more.

Get a PC. Ditch Windows. Put Linux on it ("Mint" is grand). Load Libre Office (if it's not pre-installed), and possibly Google Chrome browser (there's lots of choice, but Mozilla isn't what it used to be).

Breathe deeply and relax.

I am gradually coming to a similar conclusion on Mac software. They are very focussed on stuff that only runs on new or newish hardware so backwards compatibility of things like Whats App for desktop is poor. Photos has been incredibly dumbed down from Aperture days and Apple are obsessed with grouping stuff with face recognition AI - which is obviously driven by smart phones.

The problem apple have is that that they have to chase a hardware and software upgrade path in order to keep making money, and that means they must force obsolescence. The other problem is that with Steve Jobs long dead, they don't have visionary leadership any more.

The smart phone market must be quite mature now. I can see little point in "upgrades" and this cynicism has spread to the young market as well it seems.

Andyp":ww8vmwng said:

Mac is late 2009 and due for replacement.

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Can't help with the IT issue, but we've been mightily chuffed with our new iMac; definitely worth the spondulicos - Rob

Many of you know and understand far more than I about the technicalities of the underlying Mac software and a Apple/PC debate is not in anyone’s best interest.
From an only slightly more than a “dumb user” of Macs the user experience up to now has been faultless. My aging mac is a late 2009 model, 14+ years old. Cost back then around £1000 IIRC , that’s £70 per annum not a bad return.
I have no doubt that PC’s of that age would have issues surrounding operating systems and 3rd party apps compatibility.
I've yet to have compatibility issues with my iPad 9th gen and HP printer.

For now I will access my Yahoo mail accounts via Firefox on the iMac which will be replaced in due course but I’ve too much else on at the moment.

One question for the techies amongst which I did not get a satisfactory answer from Apple support* is why I can still access one yahoo account on the Mail app but I cannot add another yahoo account?


*never ceases to amaze me that you do not have to have any sort of Apple support package to get through to a real Apple support person, who phoned me by the way.

problem solved, I think, fingers and everything else crossed.

I might have problems explaining this but I'll try.
In my Yahoo account I went to Security > generate and manage App Passwords> enter Apple Mail as the app then select generate a one time password.
In Apple Mail >Add Account > ignore the Yahoo option but select Other Mail Account, enter Yahoo email address and the one time password generated above-----and BINGO account now appears in OS mail.

thorough send and receive testing will have to wait.

So for now my aging iMac lives on.

Well done. Where there is a will etc

I find the Apple issues begin to emerge when running systems of different ages. So on my desk in home office is an iMac pro (2019/20 vintage). I also run a similar vintage Macbook pro laptop which is fine and an older and larger Macbook pro that is late 2013. There is now an upgrade limitation on operating system for the 2013 machine, and that limits compatibility with software that I use frequently including WhatsApp and Signal. This is not an issue if I run them browser based, but is if I run them as direct installs (which I prefer).

The other almost insurmountable issue is getting everything to sync seamlessly when you get forced into running different operating systems. Messages apps handle it fine, but bookmarks for example do not sync without clunky intervention. Even when using safari (though I actually mainly use Brave and sometimes Venturi).

I don't moan about old kit - it's Apple's fault for making computers that basically last forever. :lol: I have for example one of the first Mac Airs and that is about 15 years old and still perfectly usable were it not that the screen technology does not stand comparison with modern kit. I think in fact all of my Mac laptops dating back to the first ones (I keep them) all still work. I think the oldest is about 1992 and so that is 32 years old!

I agree the Mac vs PC debate is a road to nowhere. In my business it's PC only as we need compatibility with financial systems and their security, but I like Macs at home and always have.

To be fair to Apple my yahoo mail problems appear to stem from Yahoo wanting an extra level of security on third party mail apps.
If I could be ar$ed I would find the Apple support bod who told me the only solution was a new machine. :shock:

Over the years a few yahoo products/services have either gone mammaries up or been a source of trouble.

I would seriously advise moving your email over to Gmail. It can take a while of running the two in parallel, followed by setting up auto forward rules from Yahoo to Gmail and then just use Gmail.

I did this a couple of years back moving from NTL/virginmedia to Gmail and no regrets.

Good Luck
Bob

Bob, unless I have totally misunderstood this, isn't Andy using Mac Mail as his main email programme, in which he has also set up two Yahoo mail accounts (and possibly others)?

In system preferences (MAC OSX) it offers you as well as the usual iCloud accounts (and built in alias options) , MS Exchange, Google (gmail), Yahoo, AOL and others.

AJB Temple":2g3izd1b said:

Bob, unless I have totally misunderstood this, isn't Andy using Mac Mail as his main email programme, in which he has also set up two Yahoo mail accounts (and possibly others)?

In system preferences (MAC OSX) it offers you as well as the usual iCloud accounts (and built in alias options) , MS Exchange, Google (gmail), Yahoo, AOL and others.

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You may well be correct but I'd advise against continuing to use yahoo to provide the email service.
Mac mail surely is only the local display tool that as you say talks to yahoo servers and should talk to all other mail providers.

Apple themselves may well also provide mail services not sure.

Bob

AJB Temple":yr57pgmr said:

Bob, unless I have totally misunderstood this, isn't Andy using Mac Mail as his main email programme, in which he has also set up two Yahoo mail accounts (and possibly others)?

In system preferences (MAC OSX) it offers you as well as the usual iCloud accounts (and built in alias options) , MS Exchange, Google (gmail), Yahoo, AOL and others.

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That’s right Adrian,
What Yahoo have started to do is insist on an extra level of security when using third party apps. They obviously would prefer you to only use their own app. The normal way of adding a yahoo mail account to Mac Mail is to enter the email address and user generated password in the system preferences as you describe, this no longer works. A one time password specific to the chosen mail app has to be generated by yahoo .

I do have a gmail account, also accessed from Mac Mail. One day i will migrate away from yahoo.

9fingers":urbxjytg said:

AJB Temple":urbxjytg said:

Apple themselves may well also provide mail services not sure.

Bob

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Yes, they do Bob and always have. Early adopters will have a .mac email address, and then they got .me and now .icloud (all remain valid but you can no longer get a .mac address if you don't already have one). This works as a native mail account that fully syncs across all apple devices, and also in a web browser if you prefer (or access mail on a device with no account set up). You can set up as many mail accounts as you like, from other providers and have these as a variety of inboxes within the desktop (or web) Mail app. They will also show up on a car smart screen via iPhone if that floats your boat. You can shift stuff between the inboxes / accounts very easily and activate any or all at any time as you wish.

I agree though that Yahoo is poor nowadays and has weak functionality (especially in the free version) compared with modern mail servers. Yahoo is handy to have sometimes as an email burner account, especially if you do not wish to expose your real details to (for example) online shopping apps. Sounds like they have now woken up and upped the security requirements, which were a bit weak in the absence until recently of two factor authentication. I think they still provide unlimited space, so some people used to use it to archive stuff off.

I do use yahoo’s unlimited storage. I’ve emails going back to 2006 :shock: occasionally comes in handy when I want to find out when and where I ordered something.
I am increasingly using the gmail account for “official” communications and my gmail archive goes back to 2006 too.

AndyP said:

problem solved, I think, fingers and everything else crossed.

I might have problems explaining this but I'll try.
In my Yahoo account I went to Security > generate and manage App Passwords> enter Apple Mail as the app then select generate a one time password.
In Apple Mail >Add Account > ignore the Yahoo option but select Other Mail Account, enter Yahoo email address and the one time password generated above-----and BINGO account now appears in OS mail.

thorough send and receive testing will have to wait.

So for now my aging iMac lives on.

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I just registered on this site to say thanks — I've had this issue and couldn't resolve it using the usual methods suggested on all the Mac sites.

Your workaround has fixed things and it's no longer driving me mad!

You’re welcome Californium, interesting moniker; a very rare and very expensive metal.

Always been a bit of a metalworker more than wood, if that's not blasphemous to say here...