Need help fixing Outbound email issue

We need to be able to send out Company emails.

They are all stuck in our outbox with Error: Send Report Error - Contact Server Administrator.

If someone could respond soon, it would be much appreciated.

Responses

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ralph3205

3 Messages

•

240 Points

6 days ago

I'm having the same problem . . . . started over an hour ago

1

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

Having the same issue...................had this issue a few weeks ago as well. Think Homestead is doing updates or requiring us to change something but they are NOT tell us about it in advance of our receiving error message(s)

2

0

L

lori8469

38 Messages

•

482 Points

@ralph3205 They claimed to me that Outlook changed their mapping requirement. I think it's more likely that Homestead did since it doesn't seem to be limited to Outlook users.

They need to communicate when they make massive changes like this. I was incapacitated from sending work emails all day and now many of my saved folders and emails are lost. I may have to look for another email provider. This happens too often.

Like

Reply

5 days ago

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

gary9928

12 Messages

•

300 Points

6 days ago

I have the same issue.

2

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

L

lori8469

38 Messages

•

482 Points

6 days ago

Same problem all day. On hold with support right now.

2

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

S

stephen9265

3 Messages

•

100 Points

6 days ago

Same issue, amy updates?

3

0

S

stephanie6327

7 Messages

•

140 Points

Change password and account settings in outlook.

Like

Reply

6 days ago

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

S

stephanie6327

7 Messages

•

140 Points

6 days ago

Just got off the phone with support.

If you have an old password, you need to go into homestead settings and change it so that is has:

lower case

upper case

numbers

special character

Then change your account settings to:

For IMAP account setting
Incoming server = imap.homestead.com
Outgoing server = smtp.homestead.com

For POP account setting
Incoming server = pop.homestead.com
Outgoing server = smtp.homestead.com

(edited)

4

0

ralph3205

3 Messages

•

240 Points

Thank you, Stephanie, for staying with it and sharing what you found.

Unfortunately for me, the rep I spoke with told me to REMOVE my Outlook email and start all over. I did that, she then walked me through the steps you noted above and now my system works, HOWEVER, I lost ALL my info in the Outlook file she told me to remove. BIG MISTAKE!!!

I'm in a TOTAL mess over here but do appreciate you sharing what you found out yesterday.

P.S. Did ANYONE from Homestead ever post this simple fix they shared with you over the phone? I haven't checked this morning but as of late yesterday afternoon I had seen nothing from them.

Like

Reply

6 days ago

0

S

stephanie6327

7 Messages

•

140 Points

Oh, no.

I would Google, "How to recover a deleted Outlook data file"

Hopefully you can get everything back.

Like

Reply

5 days ago

0

L

lori8469

38 Messages

•

482 Points

@stephanie6327 I did this also, didn't remove Outlook, but changed the settings in Outlook, and unfortunately, I LOST many emails and email folders that I had setup in my Outlook.

The Homestead team is supposed to be helping with this today but I'm not confident. I think that if you have any email folders that are not synched with the Homestead server, they will be lost.

Back up your emails before you change the server settings and make sure that you have the emails and folders synched with the Homestead server!

(edited)

Like

Reply

5 days ago

0

carl4822

17 Messages

•

302 Points

@stephanie6327

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

L

lisa8315

1 Message

•

60 Points

5 days ago

EMAIL CLIENT LIKE OUTLOOK OUTGOING MAIL ISSUE

For IMAP account setting
Username = Email Address
Password = your email password
Incoming server = imap.homestead.com
Outgoing server = smtp.homestead.com
Incoming port = 143
Outgoing port = 587

Turn the encryption/SSL setting to the OFF/NONE position.

For POP account setting
Username = Email Address
Password = your email password
Incoming server = pop.homestead.com
Outgoing server = smtp.homestead.com
Incoming port = 110
Outgoing port = 587
Please change the encryption/SSL setting to the Off/NONE position for both incoming & outgoing.

Important Note: Software changes rapidly. If you see a future version of something we are missing, let us know. We will see if we can get it done. Keep in mind, newer versions often look the same or similar. Our settings are not changing, so you may be able to make it work.

2

0

L

lori8469

38 Messages

•

482 Points

We need an option to allow encryption. What are the settings to have encryption ON?

Like

Reply

5 days ago

0

carl4822

17 Messages

•

302 Points

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

Like

Reply

5 days ago

0

D

daniel6817

12 Messages

•

210 Points

5 days ago

I am having issues also. Worked with two different phone support people.

Finally messed with security settings and got it to work, but every time I restart Outlook I see this.

If I click yes, outgoing email works for a while, then quits and I have to close Outlook and go through

the process. Seems this is a Homestead / Sectigo problem, not Microsoft.

0

carl4822

17 Messages

•

302 Points

5 days ago

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

0

carl4822

17 Messages

•

302 Points

5 days ago

MY settings that fixed this problem that started 2026-01-28.

I changed my Homestead and email password first.

pop.homestead.com SSL Port 995 incoming.

smtp.homestead.com SSL Yes to Server requires authentication (use same settings and my incoming mail server)

All good again.

My Outlook version 2021

0

stephanie6327

Need help fixing Outbound email issue

ralph3205

carl4822

ralph3205

lori8469

carl4822

gary9928

carl4822

carl4822

lori8469

carl4822

carl4822

stephen9265

stephanie6327

carl4822

carl4822

stephanie6327

ralph3205

stephanie6327

lori8469

carl4822

lisa8315

EMAIL CLIENT LIKE OUTLOOK OUTGOING MAIL ISSUE

lori8469

carl4822

daniel6817

carl4822

carl4822

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