Hi Everyone. I’m new to using the forum, so I hope I’m posting this appropriately – apologies if not. So, I have a client using Outlook 2016 on Windows 10/1909. He has several email accounts, but the problematic one is a Gmail account set up as POP3. Starting about a week ago, the account can receive email, but when sending email, it immediately prompts for a password (SMTP). Nothing will send – it gets stuck in the Outbox. I know it’s not a password issue – can login just fine at gmail.com. Tried deleting Outlook references in Credential manager. Checked to make sure his gmail account has POP enabled. Tried creating a new profile, including a new IMAP profile. Tried using a gmail generated secure password. Checked all server settings. Tried Microsoft Office repair tools. Tried uninstalling and reinstalling Office. No luck. One other piece of information that might be useful, is that when I try to go to Update Password, it’s unsuccesful, but that might be because this results in getting the SMTP/password prompt. I’m at wits end, and could really use some help. Thanks in advance…
![]() |
Patch reliability is unclear, but widespread attacks make patching prudent. Go ahead and patch, but watch out for potential problems. |
SIGN IN | Not a member? | REGISTER | PLUS MEMBERSHIP |
-
Gmail account in Outlook won’t send emails…
Home » Forums » AskWoody support » Productivity software by function » MS Outlook and email programs » Gmail account in Outlook won’t send emails…
- This topic has 19 replies, 10 voices, and was last updated 2 years, 10 months ago.
Viewing 12 reply threadsAuthorReplies-
anonymous
Guest -
anonymous
GuestDecember 2, 2020 at 5:21 pm #2316643Close, but no cigar! Some detail is missing:
1. Log into the google account via google webmail service using a browser.
2. go into the multitude of email settings within the account
3. look for POP3 and ‘allow insecure apps’ to access pop3 via client email apps.
4. save and log out of ebmail gmail account
5. try sending via outlook again :)/
-
-
Mike
AskWoody PlusDecember 2, 2020 at 6:48 pm #2316676BleepingComputer has several new articles on Win10 updates and how they may be affecting Outlook.
Here’s one
-
RDRguy
AskWoody LoungerDecember 2, 2020 at 7:17 pm #2316682Thanks but … I believe your link applies to Windows 10 version 2004.
Google does consider MS Outlook (especially older versions like 2013 & earlier) to be an “insecure app” and periodically they disable the insecure apps setting without any advance notice or your permission (unless it’s already there in their ULA).
This happens to us every couple of months or so running Win7 & Win8.1 and our first indication that Google turned it OFF is Outlook starts asking for our password(s) again & Outlook still fails to log into our gmail accounts even if we do enter in the password(s).
As with everything else Google, they seem to know what we want before we want it even though we really don’t want it
Win7 - PRO & Ultimate, x64 & x86
Win8.1 - PRO, x64 & x86
Groups A, B & ABS
-
-
pmoritz
Guest -
RDRguy
AskWoody LoungerDecember 4, 2020 at 9:08 pm #2317228If your Google “insecure apps” setting is “enabled” & you’re still having problems sending emails, verify your gmail POP & SMTP server port settings are set correctly in Outlook per “gmail” instructions posted here.
For secure transmission, use port 995 for POP, 587 for SMTP with encryption type TLS (or Auto).
Microsoft still suggests using the “implicit” TLS port 465 in Outlook settings for gmail here but gmail port 465 now only works (recent change?) with encryption type set to SSL, not TLS or Auto.
Additional info describing differences between SMTP ports 465 & 587 can be found here.
My working Outlook 2013 gmail POP3 account setting’s are:
Good luck
Win7 - PRO & Ultimate, x64 & x86
Win8.1 - PRO, x64 & x86
Groups A, B & ABS
-
-
Vincenzo
AskWoody Plus -
doriel
AskWoody LoungerDecember 5, 2020 at 2:08 am #2317251Microsoft and some other vendors consider POP and IMAP protocols as outdated and unsecure. Maybe its just matter of enabling these functions on Windows Defender/ firewall/ router? Not sure, just trying to help here. Im also thinking about DNS, if your PC can translate these POP and IMAP servers corrently to valid IP addresses.
Dell Latitude 3420, Intel Core i7 @ 2.8 GHz, 16GB RAM, W10 22H2 Enterprise
HAL3000, AMD Athlon 200GE @ 3,4 GHz, 8GB RAM, Fedora 29
PRUSA i3 MK3S+
-
pmoritz
AskWoody PlusDecember 5, 2020 at 11:12 am #2317300If your Google “insecure apps” setting is “enabled” & you’re still having problems sending emails, verify your gmail POP & SMTP server port settings are set correctly in Outlook per “gmail” instructions posted here.
For secure transmission, use port 995 for POP, 587 for SMTP with encryption type TLS (or Auto).
Microsoft still suggests using the “implicit” TLS port 465 in Outlook settings for gmail here but gmail port 465 now only works (recent change?) with encryption type set to SSL, not TLS or Auto.
Additional info describing differences between SMTP ports 465 & 587 can be found here.
My working Outlook 2013 gmail POP3 account setting’s are:
Good luck
Thanks so much to all of you who responded to my request, and a particular thanks you to RDRguy. Even though both Google and Microsoft said to use port 485 for SMTP, when I switched it to 587, my clients problem went away. So happy – I feel like I now have a wonderful support group to help me!
1 user thanked author for this post.
-
RDRguy
AskWoody LoungerDecember 5, 2020 at 8:14 pm #2317408pmoritz said …
“… both Google and Microsoft said to use port 485 for SMTP …”
I suspect you meant to say port “465” not “485” for SMTP server port.
BTW, SMTP port 465 still works with Gmail as long as you set your encrypted connection type (for outgoing server) to SSL.
A while back Google’s SMTP port 465 did work with a setting of either SSL, TLS or Auto for outgoing server but Google has since changed it to SSL only – at least that’s what my anecdotal testing confirmed when I suddenly had this problem earlier this year.
Win7 - PRO & Ultimate, x64 & x86
Win8.1 - PRO, x64 & x86
Groups A, B & ABS -
PKCano
ManagerDecember 6, 2020 at 5:12 am #2317483It has been my experience in the past that port 465 has worked for local connections. Example: you are connected to a home modem connected to the ISP’s cable and have thus established a secure connection to the email server because you were already logged in by virtue of the direct connection to a known registered secure device. So you didn’t need to specify secure protocols.
Port 587 was needed for a secure connection when using the ISP’s web-based email server or device not associated with your ID, and required secure protocols because you weren’t already logged in by virtue of a known registered secure device. Example: you use email from a non-local connection like a coffee shop using their wireless connection.
I think most of the ISPs have now gone to port 587 using secure protocols regardless of the connection.
1 user thanked author for this post.
-
-
-
pmoritz
GuestDecember 6, 2020 at 9:11 am #2317498Well, it looks like I spoke too soon. About an hour after I was able to successfully send email, it abruptly reverted back to prompting me for the outgoing email password. There is a send/receive error stating that the username or password are incorrect. Since I know these to be good, I’m beginning to think that maybe there’s a corrupt pst file. Does this make sense, and if so, is scan.pst still the way to go?
-
RDRguy
AskWoody LoungerDecember 7, 2020 at 7:00 am #2317787I would expect Outlook to put up some sort of “.pst error” message upon opening Outlook or attempting to read an email msg previously downloaded and already contained within your .pst file but I really don’t know as (to my knowledge) I don’t think I’ve ever had a corrupted .pst file.
One last thing I can think of is maybe your “Server Timeouts” slider setting on Outlook’s advanced settings tab is set too short in your system’s environment (Outlook/Windows version, ISP internet connectivity/bandwidth, etc) so Outlook isn’t allowing enough time for Gmail (Google) to respond to the login request & timing out then assumes wrong credentials were sent so asks for your login credentials again.
Though in my environment, Outlook 2013’s default of 1 minute seems to be adequate, Gmail (Google) recommends a Server Timeouts setting of:
Greater than 1 minute (5 is recommended)
Try moving the slider towards the middle or even all the way to the right to see if this resolves the intermittent login failures.
If you still want to set your mind at ease & perform a .pst scan, Microsoft instructions can be found here, here & here.
Win7 - PRO & Ultimate, x64 & x86
Win8.1 - PRO, x64 & x86
Groups A, B & ABS1 user thanked author for this post.
-
-
ScotchJohn
AskWoody LoungerDecember 7, 2020 at 4:19 am #2317760Pmoritz – I can’t see from the thread that you have gone into your Gmail account to generate a secure password, see this: Sign in using app passwords
I use Gmail over Outlook 2010. Seemingly, as long as I was at home, Gmail did not regard my log-in as insecure. But, the moment I went travelling, it kept on bugging me to generate a secure password, and enter it in place of my normal account password in Outlook.
Once I cracked that, no further problem.
Dell E5570 Latitude, Intel Core i5 6440@2.60 GHz, 8.00 GB - Win 10 Pro
-
RetiredGeek
AskWoody_MVPDecember 7, 2020 at 1:05 pm #2317858I second ScotchJohn’s recommendation, in fact it is required if you have two factor authentication set up on your gmail account. I have 2fa setup on all my gmail accounts and have no problems using Outlook 2010 or 365 for my email client.
HTH
-
This reply was modified 4 years, 4 months ago by
RetiredGeek.
-
This reply was modified 4 years, 4 months ago by
-
anonymous
GuestDecember 15, 2020 at 10:59 am #2319794Hi Everyone – Sorry it’s been so long since I responded to my post. I felt I should update you on how I finally resolved my clients’ problem. It’s a little bit embarrassing, but what I finally figured out was that my clients’ Gmail space was used up – over 100,000 emails! After deleting about half of them from the Gmail server, everything started working again. Thanks so much to all of you for your suggestions, I appreciate everyone who took the time to try to help me…
-
anonymous
GuestMay 16, 2022 at 9:32 pm #2447281I had the same problem, received OK but kept asking for password when I tried to send a gmail email in outlook, tried different ports 465 and 587, checked less secure apps was turned on and 2FA turned off. checked TLS1.3 wasn’t enabled. I found this solution that worked for me something about captcha.
clicked on the link in this article https://accounts.google.com/DisplayUnlockCaptcha
and now am able to send gmail emails in outlook.
-
DickC
GuestJune 9, 2022 at 11:08 pm #2452333I can no longer use MS Outlook 2013 to send and receive emails through my Gmail account using its POP3 service. Everything was working very well until June 7, 2022 – then it began requiring the entry of ID and Password over and over again. With your help a couple of years ago when I had this problem, I had set Outlook as an insecure App, and that gained access. Now, I tracked this problem back and discovered a Google update such that Gmail will no longer allow access to insecure Apps such as Outlook in any variety. They kicked me to the curb and I don’t know how to recover. Gmail’s native mail reader sucks compared to Outlook, but I am stuck. Any suggestions?
-
Susan Bradley
ManagerJune 9, 2022 at 11:10 pm #2452335Topic: How to use MS Outlook 2003 to access a Gmail account with 2-Step Verification @ AskWoody
Topic: Accessing gmail from Outlook 2019, POP3 account, as a “secure” application? @ AskWoody
Canon Knowledge Base – How to setup Scan to Email using Gmail (imagePROGRAF MFP Z36 Scanner)
See if these help?
Susan Bradley Patch Lady/Prudent patcher
Viewing 12 reply threads -

Plus Membership
Donations from Plus members keep this site going. You can identify the people who support AskWoody by the Plus badge on their avatars.
AskWoody Plus members not only get access to all of the contents of this site -- including Susan Bradley's frequently updated Patch Watch listing -- they also receive weekly AskWoody Plus Newsletters (formerly Windows Secrets Newsletter) and AskWoody Plus Alerts, emails when there are important breaking developments.
Get Plus!
Welcome to our unique respite from the madness.
It's easy to post questions about Windows 11, Windows 10, Win8.1, Win7, Surface, Office, or browse through our Forums. Post anonymously or register for greater privileges. Keep it civil, please: Decorous Lounge rules strictly enforced. Questions? Contact Customer Support.
Search Newsletters
Search Forums
View the Forum
Search for Topics
Recent Topics
-
Trying to backup Win 10 computer to iCloud (Awaiting moderation)
by
SheltieMom
12 minutes ago -
Windows 11 Insider Preview build 26200.5570 released to DEV
by
joep517
6 hours, 49 minutes ago -
Windows 11 Insider Preview build 26120.3941 (24H2) released to BETA
by
joep517
8 hours, 37 minutes ago -
Windows 11 Insider Preview Build 22635.5305 (23H2) released to BETA
by
joep517
8 hours, 38 minutes ago -
No April cumulative update for Win 11 23H2?
by
Peobody
10 hours, 56 minutes ago -
AugLoop.All (TEST Augmentation Loop MSIT)
by
LarryK
9 hours, 10 minutes ago -
Boot Sequence for Dell Optiplex 7070 Tower
by
Serge Carniol
1 day ago -
OTT Upgrade Windows 11 to 24H2 on Unsupported Hardware
by
bbearren
1 day, 3 hours ago -
Inetpub can be tricked
by
Susan Bradley
1 day, 5 hours ago -
How merge Outlook 2016 .pst file w/into newly created Outlook 2024 install .pst?
by
Tex265
8 hours, 30 minutes ago -
FBI 2024 Internet Crime Report
by
Alex5723
1 day, 7 hours ago -
Perplexity CEO says its browser will track everything users do online
by
Alex5723
19 hours, 22 minutes ago -
Login issues with Windows Hello
by
CWBillow
1 day, 18 hours ago -
How to get into a manual setup screen in 2024 Outlook classic?
by
Tex265
1 day, 6 hours ago -
Linux : ARMO rootkit “Curing”
by
Alex5723
2 days, 6 hours ago -
Employee monitoring app leaks 21 million screenshots in real time
by
Alex5723
2 days, 6 hours ago -
Google AI is now hallucinating idioms
by
Alex5723
2 days, 6 hours ago -
april update
by
69800
11 hours, 9 minutes ago -
Windows 11 Insider Preview build 27842 released to Canary
by
joep517
2 days, 7 hours ago -
Quick Fix for Slowing File Explorer
by
Drcard:))
2 days, 7 hours ago -
WuMgr not loading?
by
LHiggins
1 day, 3 hours ago -
Word crashes when accessing Help
by
CWBillow
1 day, 12 hours ago -
New Microsoft Nag — Danger! Danger! sign-in to your Microsoft Account
by
EricB
2 days, 7 hours ago -
Blank Inetpub folder
by
Susan Bradley
2 days, 5 hours ago -
Google : Extended Repair Program for Pixel 7a
by
Alex5723
2 days, 18 hours ago -
Updates seem to have broken Microsoft Edge
by
rebop2020
2 days, 4 hours ago -
Wait command?
by
CWBillow
2 days, 11 hours ago -
Malwarebytes 5 Free version manual platform updates
by
Bob99
3 days ago -
inetpub : Microsoft’s patch for CVE-2025–21204 introduces vulnerability
by
Alex5723
3 days, 7 hours ago -
Windows 10 finally gets fix
by
Susan Bradley
3 days, 16 hours ago
Recent blog posts
Key Links
Want to Advertise in the free newsletter? How about a gift subscription in honor of a birthday? Send an email to sb@askwoody.com to ask how.
Mastodon profile for DefConPatch
Mastodon profile for AskWoody
Home • About • FAQ • Posts & Privacy • Forums • My Account
Register • Free Newsletter • Plus Membership • Gift Certificates • MS-DEFCON Alerts
Copyright ©2004-2025 by AskWoody Tech LLC. All Rights Reserved.