Microsoft has patched a security thingie, recently on all recent server OS’es.
Every good citizen, using the default Remote Desktop software, has a big chance to be screwed.
You’ve just imported somebody’s mailbox in a lovely new Office 365 or local Microsoft Exchange Server, coming from a somewhat older system running on IMAP or an other cool 80’s-90’s e-mail protocol.
After struggling with all the necessary issues you run into (getting rid of Mozilla Thunderbird, convincing the local Linux user that he should indeed run Windows for him to receive proper support from you, updating everything to the latest released patches, …), you finally get a version of Outlook up and running, with all mails, calendar and contacts.
Also, don’t forget your auto-complete list ! (NO THIS ISN’T YOUR ADDRESS BOOK)
WHEN SUDDENLY one of the following complaints come your way :
I can’t delete a certain folder in my Outlook !
One or more of my folders is empty, even though it says “xxx number of items in this folder” !
What is “FILTER APPLIED” on the bottom bar of my freshly installed Outlook and why can’t I reset my “Views” in the “Change View” menu ?
…
In this specific case, after a copy or import from an IMAP mailbox, there’ s a huge possibility that the properties of your folder that houses these mail messages is set to something faulty.
In most of these cases, it’s the so-called Container Class that still thinks that we’re working in an IMAP folder instead of a regular “Note” folder. (I didn’t invent the name)
Solving the actual problem
Before we start, I’d like to add a little disclaimer here, saying you can seriously mess up your mail folders if you just fiddle around without knowing what you’re doing in the software we’ll be using.
Download the version corresponding to your OFFICE VERSION (not your Windows version), 32 or 64 bit, unpack the zipfile and run the package.
Go to Session > Logon
Select your Outlook profile (if any)
Double-click the data store (possibly just one, depending on the rights you have to other mailboxes or extra added PST files)
Expand Root – Mailbox (or whatever it’s called in your Office installed language)
Expand the Top of Information Store or the IPM_Subtree folder
Select Inbox (language-specific name) and browse to the folder containing the problem
Doubleclick PR_CONTAINER_CLASS in the right column and change the value in the ANSI field to IPF.Note.
If my predections were correct, it used to say IPF.IMAP.
If this is not the case, stop what you’re doing and roll back your changes, as there’s a different issue.
You didn’t think I was going to let you start a migration process without making you read the detailed “how and why”, did you ?
There’s a couple of migration types to keep in mind, where one is easier than the other.
Usually the more difficult one is also the most interesting one, but even this is dependant on specific needs.
Remote move migration
Staged migration
Cutover migration
IMAP migration
PST import
The last one (PST) is in most cases forgotten as an official way, since it’s possibly way too simple in Microsoft’s eyes.
As the target audience for this specific blog post is the average Belgian SME with an average of 5 to 20 employees, I’ll stick to the basics in this post.
An other post will cover the heavier subjects in a nearby future (aka ‘when I feel like it’)
PST Migration (1)
Difficulty level
Microsoft has this pretty cool tool to either upload PST files to a temporary Azure storage or to actually send them a physical copy by mail (yes, snailmail)
It’s a bit out of the scope of our average situation here, but know that such a method exists.
It will require the use of the program AZCopy, which is well explained in the link above.
Check it out if you want to look like a cool IT guy in the eyes of your customer 😉
(although Powershell is still the way to go if you really want to impress your customer)
PST Migration (2)
Difficulty level
Being a ton easier and providing more oversight than the PST Migration above, the ‘basic’ PST migration will have the average end-user require/demand your presence more often.
Although remote tools like Teamviewer/LogMeIn/… have made the life of the IT’er a lot easier, there’s got to be a bit of physical contact every now and then. This type of migration will give you the opportunity to sit down and explain Office 365 to your users while the data is slowly uploading through MS Outlook.
Grab some coffee and get your hands dirty as this type of migration will get you closest to the actual customer’s computer than any other.
Try to avoid using this migration type, when the customer has an IMAP mail account you need to move to your O365 tenant, as often IMAP saves the mail headers, but not the mail an sich, resulting in a very empty mailbox in the end.
Now, how does this process work ?
Pretty easy :
First of all, get your mail users to stop using their mail for a while.
Preferably redirect the mailflow, by use of the MX record we talked about in this post, already 24 hours before starting your PST import, to make sure no trailing mail gets left behind on a mail server you won’t be able to access anymore after migrating.
If you’re really sure that the mail is good to go, the easiest way would be to locate the current location of the PST files. https://www.msoutlook.info/question/827 explains this quite well.
Keep in mind that the PST files aren’t always in their default location. Some customer prefer to save their PST files on a network location or redirected folder.
If you happen to be the IT guy that implemented this specific setup, shame on you. PST files will get corrupted by just looking at them. Placing them in a network drive, will only make things worse.
No PST file found ? No problem !
There’s a possibility that your user has disabled ‘cached mode’ in Outlook (often occurs in cases of local desktop computers in connection with an Exchange Server on that same location)
In that case you’re more likely to find OST files or something similar.
The ‘clean’ way to go here is to start a simple PST export procedure in Outlook
Seeing as reinventing the wheel is not my hobby, here’s the link to the Microsoft article that explains how to do this : https://support.office.com/en-us/article/export-or-backup-email-contacts-and-calendar-to-an-outlook-pst-file-14252b52-3075-4e9b-be4e-ff9ef1068f91
Writing walls of text is one of my hobbies, though ^_^
Once you’ve gotten hold of the PST files, there’s a couple of ways to get them in Office 365, but seeing as I already advised to stop your users from using their email for a while, you get to strike while the iron is still hot.
The easiest way is to create a new Outlook profile.
Mac users : check this out –> https://support.office.com/en-us/article/manage-profiles-or-identities-in-outlook-for-mac-fed2a955-74df-4a24-bef6-78a426958c4c Windows users : Open Control Panel, go to Mail (32 bits or no reference to the number of bits, depending on the version).
Afterwards, click ‘View Profiles’ and add a new one.
The ‘new account‘ wizard starts, where you can simply enter your new mail address (given you’re not migrating from a local Exchange server on your own domain – more on this later)
Outlook will start and an empty mailbox or even a partly filled one will appear. Depending on whether you changed the MX record already or left it unchanged.
Eventually, change the default profile to your new O365 one.
Repeat x times where x is the number of computers where Outlook is running the old mailbox.
IMAP migration
Difficulty level
The difficulty level could vary depending on the version of the IMAP server, but the thought train runs on that same track. (did I just invent a new proverb ?)
First of all, let’s take a look at this schema below, which explains the process of migration quite neatly and in an understandable manner.
Thanks, Microsoft, for this overview.
If you’ve followed our current steps in the previous posts, we’ve already established the steps up to the creation of the mailboxes, which starts us at step 5. isn’t that tidy ?
You need to create a specific CSV file, that we’re going to use in our migration batch.
Usually it will suffice to base yourself on this template, but there are exceptions for Exchange, Dovecot, Mirapoint and couple of weirder ones.
The general idea behind this CSV file is to provide the mailbox address TO which you need to copy the content of the IMAP folder, together with the username and password of the ORIGINAL IMAP mailbox, where the mail is currently residing.
You can start the migration in the O365 Exchange Control Panel, by going to ‘Recipients’ and then clicking ‘Migration’ in the topmenu.
Click the little ‘+‘ and select ‘Migrate to Exchange Online’
Select ‘IMAP migration’
Upload your CSV file and allow unknown columns
Enter the IMAP server data and means of authentication of your old provider
Pressing ‘Next’ will start the initial setup.
The migration top menu will provide you with more information on how your migration is going. You can click the migration batch and review potential errors or view the overall progress.
A picture’s worth a thousand words, so I’m guessing a Youtube video will be worth at least “De Leeuw van Vlaenderen” :
Every IT related action has a counter-action that results in something going wrong.
Keep Murphy’s laws in mind, especially the computer-based ones.
Oh no! I lost my contacts.
First of all, wear glasses.
Second, they’re not your contacts. They’re your autocomplete list in the to-field
Third, you might have used the global address list instead of your own contact list.
Still found no contacts ? Have you imported from a different folder language of Outlook ? Check ‘all folders‘ and see if you’ve got an other ‘Contacts’ folder somewhere (check for specific Contacts icons)
Also, an IMAP migration does not cover contacts (or calendar or tasks for that matter, import them using the PST method, while excluding mail)
I can’t send an internal mail after the O365 migration.
Actually, you can, but you’re still using the wrong address in the background.
Your to-field might say ‘my_colleague@mydomain.com’, but in the background it’s saved this entry as a unique ID (especially when migrating from your own local mail server).
The solution : delete this user from your address book/autocomplete list and type the address manually.
I didn’t have Outlook before migrating. How can I create this new profile you speak of ?
2 do : tools for migrating from other crappy software
My PST file will not import (/partly).
Most common reason is a corrupt PST file. Fix it using the scanPST tool.
Corruption can happen if you save your PST file on a network drive or if a specific mail is being a d*ck. ScanPST will solve this.
An often overlooked reason could also be not having enough space in your new O365 mailbox. In this case you might have to upgrade the O365 subscription for this specific user with extra space or clean up the mailbox before doing the export to a PST file.
Very big mails don’t get IMAP-migrated.
This is normal. IMAP migration supports email size up to 35MB/mail
I had a sh*tload of mails in my old IMAP folder and now some of them are missing.
If you had over 500.000 mails in your old IMAP box, this is bound to happen as number of maximum items you can migrate in one batch is limited to 500.000
Migrating from Google to O365 is constantly failing. What am I doing wrong ?
You haven’t google’d enough.
No, seriously, there’ s a security setting you must turn on in your Google Security Settings :
You’ll find this here : https://myaccount.google.com/security?pli=1#signin
If you’re born before 1990 (and if you’re in IT), you probably grew up with self-signed certificates.
They give you a lovely fake feeling of security, but more than that, they will give users and the IT department horrible stress to configure.
In “days of olde” (early 2000’s), an Exchange server was able to run over http traffic and a certificate was absolutely not required.
Times have changed and so have security protocols. It’s ill-advised to use a self-signed certificate nowadays, as it is equally ill-advised to use a .local domain anymore on your domain controller.
That being said, there’s a couple of ways to fix an expired self-signed certificate on a Windows SBS server. (read first, perform later, you’ll see why)
Lazy mode
aka ‘fix my network’
Open the SBS console, go to the ‘network’ menu and select the ‘Connectivity’ tab.
Click ‘Fix my network’ and deselect everything except the certificate error, after this wizard stops scanning.
The usual Next-Next-Next will follow and according to Microsoft, you’re good to go.
HOWEVER…
There’s a couple of things that can go wrong here :
Your certificate contains a custom entry referring to a domain name or subdomain name that wasn’t originally added in the SBS wizard.
You’ll need to perform the manual method for renewing a certificate. See below.
Your Exchange webmail (https://your_mail_server_ip/owa/) still gives a certificate error, stating your certificate’s still expired.
Start the ExMngmtnShell (Exchange Management Shell) as Administrator
type Get-ExchangeCertificate to list the installed certificates
Match the certificate to the expired certificate (using subject the name and services) from the Console then copy the associated thumbprint
Type Get-ExchangeCertificate –Thumbprint INSERTTHUMBPRINTHERE | New-ExchangeCertificate | Enble-ExchangeCertificate -services pop,imap,smtp,iis
Type Y to renew the certificate
Restart SBS2008/2011 Console or restart server.
Profit.
Like-a-bawz-mode
Beautifully explained on http://www.petenetlive.com/KB/Article/0000535, so no need to repeat what Pete already wrote.
The main idea here is to use the IIS built-in Certification Authority (certsrv), while manually defining all entries needed in the certificate.
It’s still relatively easy, but requires a lot of steps.
Of all three mentioned methods, this last one is most likely to succeed.
In our previous post, we’ve set up everything so we’d be able to start creating the users and their respective mailboxes.
If at this point you’ve already changed the mail server name in the domain’s MX record to that of the Office 365 one, remember that actual mail might already be arriving (or bouncing) in the O365 environment, so be cautious of this, when migrating a live situation.
A small recap below in case you forgot our intended setup :
Veritas !
If you’ve been paying attention in the previous posts, you’ll know we will be needing to create three users here :
Oliver
Annie
John
All other mail related stuff will be handled with mail groups or shared boxes.
Remember : the Microsoft licensing system in O365 is user-based, not computer-based.
Let’s start off with creating these three accounts.
Open the Office 365 admin portal and open the “Users” menu, and then select “Active Users”.
Next, Click the “+ Add a user” button and a small form appears.
Creating a user
You’ll notice a couple of things in the user creation form (except from the obvious things of course) :
The domain field shows your recently added domain as well as the onmicrosoft.com tenant name.
This means that you’re not obliged to actually use a domain name in an O365 environment. When going for mailboxes, it’d be stupid/silly/… not to do so.
Password generation : either let Microsoft generate a password for you that complies with the O365 password policies or type one for yourself.
You can also allow the user to be able to change their password on first logon.
Make your choice depending on the end-customer’s needs.
After confirming the user creation, you’ll also be given the option to send the credentials to an email address of your choice.
Roles : by default, new users will be given the “User” role, which allows for basic usage of the O365 environment. Other roles can be “Global administrator” or a custom mix of rights.
For more info on the different types of admin rights, see this Microsoft page.
If you’re ever to go and do a Microsoft exam on O365, these roles will pop up more than once in the questions list.
The Roles parts also allows you to fill in an alternative email address, instead of the user having to do this. Purely intended for password retrieval purposes.
Product licenses : in the O365 demo you’ll be given 25 Enterprise E3 licenses.
Depending on your user’s needs, provide the correct licenses by clicking the slider next to the license name.
Creating an user without a product license, which is also an option, is ill-advised and used in only a few specific situations.
Click the “Add” button and you’ll be greeted with the send-password screen asking you if you need to send the password in case you forget to write it down.
Repeat for all the necessary users.
In this case Annie and John will be created in the same way.
Remember to remove the admin’s E3 license for good measure. (but keep him admin !!)
In this demo environment, it doesn’t really matter, but you don’t want your customer to be paying for an unused license.
Just a tiny heads-up : if you don’t want your users to be calling you every 90 days, you might want to perform the small task of changing the Password policy.
Go to Settings > Security and Privacy and change password policy to “Never expire” and “Never notify” by clicking the “Edit” button.
The spice must flow. So must the mail
Well, that didn’t seem so difficult, right ?
Office 365 has automatically created a mailbox already for your users, in the background.
The system knid of predicted that you’d be wanting a mailbox for your E3-licensed users, as otherwise it wouldn’t be logic that you’d provided them with such a license. Of course there’s still some things that need to be done, so let’s have a look there.
There are two ways to edit mailbox properties.
The easiest, but with the least fancy options is through the same “User” menu we used to create the users themselves.
The second option is through the Exchange Admin Center.
Let’s start with “easy mode” :
Click the user in the Active Users menu and his properties will appear in an overview.
One of the options visible will be “Mail Settings”, where you can set up a couple of things :
Mailbox permissions : literally what it says. Allow others to have specific access to this mailbox. We’ll get into more detail when we reach a shared mailbox.
Email forwarding : allows you to *drumrolls* forward your user’s mail to another mailbox, with the option of leaving the original mails in your O365 box.
External mailboxes (unrelated to your O365 tenant) are also possible recipients.
Litigation Hold : allows for items in the mailbox to be retained even if the user deletes them.
Pay attention that this can increase the size of your mailbox significantly.
More info on litigation can be found on this Technet article.
Automatic replies : I don’t believe this needs much explaining.
Can also be done through the user’s personal settings in either Outlook or throught https://outlook.office365.com and preferably so. If you need to manage all your customers’ mailboxes and set their Out of Office message yourself, you’d best be charging by the hour.
Email apps will provide you the option of disabling certani ways of connecting to the O365 mail system. I can imaging you might want to disable POP ad IMAP for instance. It depends on the specific needs, however.
Show in global address list sets visibility of this mailbox in the address list when browsing through your company contacts. Usually you’d want this setting to remain untouched. Only in certain cases (for instance a logging or journaling mailbox) will this be a good choice.
Converto to a shared mailbox basically unlinks the mailbox from a user license and changes it to an mailbox which is only visible through an other O365 account within your tenant.
Edit Exchange properties opens the “hard mode” Exchange Admin Center screen, which we’ll discuss in more detail next.
The Exchange Admin Center is actually the way to go when you want to configure your mail environment in more detail.
It’s also a lot more fun to fiddle around in and it will give you a more general idea on all the mailbox features.
For all on-premise Exchange server admins with experience in 2013 server or higher : you’re in for a treat as this is an almost-perfect copy of the “Exchange Control Panel” with just a tiny difference in some functionality. You can probably skip most of this part.
Even the URL is similar : https://outlook.office365.com/ecp/
Information overload
Don’t be startled by the amount of clickable options in the Exchange admin Center.
We’ll cover the basics, under the “recipients” section.
Have a look around in the other options, but don’t change anything for now.
For your ease, click the Recipients link in the left menu.
This will show us six options in the top menu :
Mailboxes : an advanced view per mailbox for setting up rights, mailflow, aliases, …
Groups : allows for creation of either a fixed ditribution group, a security group or a dynamic distribution group. The dynamic groups are actually quite fun to play around with. They set up a mail-enable group depending on certain variables such as company name, department, …
Resources are practically identical to shared mailboxes, with the difference that they have a fancy looking icon. Resource mailboxes have the purpose of creating a mailbox (more preferrably a calendar) for your hardware.
If Oliver Shortstraw has a meeting room and a shared car, he might benefit from giving these items a calendar of their own (it’s free, anyway) so managing whoever needs to borrow the car or use the meeting room becomes a super-easy task.
Contacts : if you were to use external email addresses in tenant-wide mail rules, they need to be defined in this area.
“Mail contacts” are used for administrative purposes only.
“Mail users” are Active Directory enabled objects linked to an external mail address, allowing external users (like a gmail user) to perform things inside your cloud AD environment.
Shared mailboxes : as mentioned before, these mailboxes host mail, but aren’t linked to a physical user, thus not accounted for during licensing cost calculation.
Migration. I’ve always found this option to be somewhat misplaced in the recipients menu.
The “Migration” option oviously lets you migrate to (and from !) Exchange Online through a couple of ways.
We’ll be doing the second-to-easiest migration later on, as we’ll be importing shortstraw.be mail from the current provider over an IMAP migration.
In case you’re wondering : importing PST files in Outlook is the easiest way.
Mailbox properties
Let’s start alphabetically and have a look at Annie’s mailbox.
Doubleclick her entry in the Mailboxes part of the Exchange Admin Center
Annie, are you OK ?
The more important options in this popup window (allow popups in your browser for this to work, by the way) aren’t the ones you see at first.
Except from the “hide from address list” check mark, you can safely move on the “email address” menu for now. Feel free to have a gander at the other options.
You’ll see three entries by default, after having created a user with only one domain attached to the O365 tenant :
SIP : used in Lync/Skype for Business/Teams (the communication part)
SMTP (in uppercase) : the default address, by which all outgoing mail from this mailbox is sent. Also called the “reply address”
smtp (in lowercase) : an alias to the mailbox. Mail sent to this address will appear in the mailbox as well. Replies will be sent from the SMTP address.
In our example, we’d like for Annie to receive cfo@shortstraw.be as well.
This can be easily achieved by clicking the little + icon and filling out the form, where you type the complete e-mail address and pressing the “Save” button.
You can edit here if this new address needs to become the reply address.
Mailbox features holds a plethora of options such as disabling the use webmail, denying mobile phone connectivity, litigation (see above), archiving, …
The part I want to focus on is “Mail flow” (scroll down a little in the list or enlarge the window).
Again, feel free to check out the other options as well.
Click mail flow and a new window will appear where you get to fill out another form.
Forward, march !
Pretty straightforward option where you can setup a server-side mail forwarding, without Annie knowing about it.
For legal reasons I’m obliged to tell you that you should inform your users of this forwarding rule.
Ticking “Enable forwarding” enables you to click the “Browse” button, which in its turn shows you the list of available users to select from.
You’ll see that this list is populated only by the internal addresses in your own global address list.
And this is where our “Mail contacts” from above come in of oyu’re to setup a forwarding to an address that’s not housed in your customer’s O365 tenant.
“Deliver message to both forwarding addresses and mailbox” simply does what it says. If you weren’t to activate this after enabling the forward option, Annie wouldn’t receive mails anymore in her own mailbox, but all mails are forwarded without leaving a copy.
One more option in the left menu of our user mailbox properties that we’ll look into within a couple of minutes is the “Mailbox delegation” menu. This option is a mini rights management where you can set “full access”, “send on behalf” and “send as” rights for a mailbox.
In our example, Oliver had a couple of aliases in his old mail setup.
Because we love our customer, we’ll gladly copy and paste these addresses in the new environment so he can be mailed on e.g. tha-bawz@shortstraw.be
Our third “straw” is John, who luckily doesn’t need extras so he’s good to go with an out-of-the-box setup, which starts him up automatically as john@shortstraw.be
We’re almost done with our basic mailflow configuration.
All that remains from our initial analysis (concerning the shortstraw.be domain name) is the remaining info@shortstraw.be that needed to be seen by both Annie and Oliver.
We’ve already established that a shared mailbox would be the most appropriate solution for this, so let’s configure one !
Go to the “shared” top menu and click the little + icon.
A familiar looking form appears.
You might recognize this from when you just recently created a new mailbox.
The biggest difference is the appearance of the permissions box.
Select the user(s) with permission to view and send from this box and press “Save”.
You’re good to go !
Setting up a shared mailbox is THAT easy.
You’ve got a basic mail configuration up and running.
If you’ve changed the DNS settings for the MX record as discussed in the previous migration post, you should be receiving mail by now.
If you’ve set up this mail config as a placeholder for when the actual migration starts, it’s time to move on to the migration now.
THAT’S RIGHT !! YOU GET TO ACTUALLY MIGRATE AFTER 5 CONSECUTIVE POSTS CLAIMING SO.
All jokes aside, in my humble opinion the prep work is incredibly important in deciding between keeping or losing your customer.
And that’s a decision from both the customer and the IT guy/girl !
First of all, SPF stands for “Sender Policy framework”.
Now you know.
Period.
Just kidding.
An SPF record is used as a “sort of ” security/anti-spam measure in order to protect your outgoing mail from being sent FROM a certain list of sender locations.
You read it right : “from” (not “to“).
It’s in no way a fail-safe antispam solution, but it will decrease the amount of mails sent in your name significantly.
Office 365 even requires this specific record on first setup (although you can skip this step eventually).
Who didn’t configure his Outlook Express in the old days to send mail from as his boss to fake a “you’re fired” mail to your new colleague ? Right ? Right ? N-Nobody ?
Oops. Sorry, Bjorn.
In order to understand how things work, wel’ll start out with a little example from our fake (?) company Shortstraw LLC and their Office 365.
After setting up your O365 subscription, your SPF records looks a bit like this :
Note the “subtle” reference to mxtoolbox.com
I deliberately used the expression “text record” as SPF is nothing more than a TXT record with a specific markup. Most hosting companies have a separate entry box for SPF nowadays, but in the background it’s still a TXT.
Let’s split up everyting in this text record, so we can understand completely what exactly it is that Microsoft wants us to do.
v=spf1 :
All this does is stating the obvious.
This record is “version SPF1”.
To make things confusing, there’s an unrelated spf2.0 record, which stands for “Sender ID”
include:spf.protection.outlook.com :
The include value *drumrolls* includes the values of another SPF record, in this case a large list of IP addresses of Microsoft servers.
The very same website I’ve used in the example above (MX Toolbox) easily provided me with this information. You can see that in itself this record loops through to more SPF values in spfa.protection.outlook.com.
This has to do with the maximum accepted length for a TXT record, which is limited to 255 characters, as explained on this RFC page.
-all The final entry in the record is also the most conclusive one.
The “-all” stands for “disallow all other entries”
Other entries
The above example was just a textbook sample provided by Microsoft to get you started. It should be sufficient for the average O365 setup.
Reality however will often slap you in the face with a more complex situation where you’ll be needing to configure all-in-one printers, old software packages with support for mail over port 25 only, websites sending from something@your_domain_name, …
They all have a couple of specific things to keep in mind when configuring your SPF record.
A handy tool for helping you configuring your SPF record is https://www.spfwizard.net/, which does exactly what the name implies.
Other possible entries you might use in your record :
A:
It’s usually followed by an actual DNS A-record
An example will make things clear.
The classic O365 SPF record was added a:mail.suamae.br, which will allow the IP resolving to this Brazilian mail server name to be able to send mails from shortstraw.be’s domain name as well.
Just adding “A” and not defining anything behind it, will result in all A-records in shortstraw.be being able to send mail from this domain name.
The example above will allow all the mailservers in the domain uwmoeder.com to be able to send mail from shortstraw.be
Double checking on this, it will resolve to redirect.ovh.net in this case.
Just adding “MX” without a domain name, will allow all MX entries in the shortstraw.be domain to send mail.
IP4: You may enter one specific IPv4 address or a group of IP addresses in the typical “slash” notation (it’s called “CIDR format” in big-boy-language).
Note the omission of the letter “v” in ip4. Pay attention to this common typo.
Received-SPF: softfail (google.com: domain of transitioning mail@example.com does not designate 203.0.113.2 as permitted sender) client-ip=203.0.113.2;
+all
Stating the “+all” addendum, ignores everything you just added in the previous part of the SPF record.
Your mails might (or might not, depending on the server) be tagged with an extra header that says something in the likes of “this mail is probably not OK, but it doesn’t matter anyway”.
?all
Almost the same as “+all”, with the exception that your mails will not be flagged.
?all stands for “No policy statement” and simply does not hold the SPF record in account.
Often used when trying to delete an SPF record without actually deleting it.
Now how does this REALLY work ?
Every self-respectable and up-to-date mail server will do an SPF checkup, when receiving mail.
That’s right, even Exchange Server 2003 can do this, updated to Service Pack 2. (not sure how it’s implemented in an Exchange 2000, though – I’ve seen software by GFI that used to be able to do this, but if you’ve come to this page looking for an antispam solution for your Exchange 2000, you can probably guess what I’m thinking right now…)
In a side-note, this function is usually referred to as “Sender ID” in an Exchange environment.
It’s usually a hard-coded feature with nothing much to tweak, except for turning it on or off.
A basic representation of SPF functionality (picture shamelessly stolen from this site)
One simple image explains how it works.
Mail server A sends mail from a certain domain.
Mail server B receives mail from this domain and does a quick DNS lookup looking for any TXT records containing “v=spf1” after which he interprets the information like I’ve explained about one page up.
That’s it !
You now know how an SPF record works !
More information
I’ve taken the liberty of compiling a small list of handy websites should you want to read more on the subject.
Mxtoolbox.
Your trustworthy website on troubleshooting DNS and mail related stuff. https://www.mxtoolbox.com
Microsoft Message Header Analyzer.
Not mentioned in this page yet, but a great tool nevertheless.
If reading a wall of text is too hard, copy your mail headers in this website and it will provide you with readable text. Huzzah ! https://testconnectivity.microsoft.com/?tabid=mha
Remember Oliver’s company (Shortstraw LLC) mail profile in one of our previous posts ? Refresh your memory if you stumble upon this website and have forgotten / not read the previous one.
I will base this actual setup on our findings in that post.
The hardware and operating system upgrading procedures, that I spoke about, will not be handled here.
Preparing the environment
Since we’ve established our to-do list, we can now start the procedure in which the customer will experience the least downtime.
Depending on the expectations of the customer, you can either perform all these actions on-the-fly or prepare yourself thoroughly. In this case we’ll take the long(er) road.
After having created the 30-day trial (or go ahead and buy one instantly through Microsoft or a Cloud Solutions Partner)
At least, we’re welcome
You’ll be greeted with something similar to the screenshot above.
Clicking the upper left square icon will get you into the apps menu.
Depending on the user rights and licenses, you’ll see less or more icons, representing the programs and apps you’re allowed to use.
One important icon you’ll see, is the “Admin“.
Users that have administrator rights will be provided with this option.
In this example, our admin user has a fully working E3 license (you get 25 of these buggers in an O365 trial), which is something that’s “not done” in a real life situation.
Were you to upgrade this 30 day trial to a full tenant, I strongly suggest stripping the admin account of all his licenses. It’s bad practice to use your O365 admin account for anything else than … well… admin purposes.
We’ll get into licensing later.
The admin menu
Click on “Admin” and a specific administrative portal opens.
You can take a short tour of everything by clicking “Start the tour” if you want or read onward and click “Skip”.
On the left side of the admin page you’ll notice the admin menu (which is deliberately placed as a screenshot on the right side of this page, just to confuse you)
First thing you’ll be wanting to do is to create the situation with the correct internal mailflow, user rights etc.
Remember : as long as you don’t change the MX record in the customer’s DNS settings, NOTHING will happen to the existing setup.
You can safely mess around until you’ve got the flow up and running to your own standards.
Remembering our previous conclusion, we’ll start creating our users’ mailboxes first.
If you want to get this right at first try, you’ll want to include the domain first as an “inbound” domain into your O365 tenant. This will allow you to create user names ending in @yourdomain.com instead of @yourdomain-com.onmicrosoft.com.
Again, including the domain name will not change your current mail flow.
DON’T PANIC !!!
Open the Setup menu and click “Domains”
One domain will be listed by default.
This is you tenant name (in my example “shortstraw.onmicrosoft.com”) and cannot be removed.
Click “Add Domain” and fill in the desired domain name, after which you click “Next”.
In order for Microsoft’s servers to verify your identity and double checking if you’re actually the owner or admin for your added domain, you’ll be given the choice of either adding a TXT record or adding a fake MX record into your own DNS management software at your hosting company’s admin package.
In my case, the lovely French hosting company “OVH” will be my location to turn to.
A line of TXT in OVH’s DNS management
Eventually, practically every DNS hosting company allows you to manage your settings through some form of admin portal for easy setup purposes.
Once the record has been added, you can click the “Verify” button to let Microsoft doucble check the creation of the record.
Troubleshooting :
If the TXT record is not yet found, according to the O365 domain verification wizard, you can always start your troubleshooting on a global level by surfing to https://dnschecker.org/DNS Checker creates a worldwide DNS lookup, using all sorts of DNS servers to see if your DNS record has propagated already to all locations.
Usually DNS propagation for a brand new domain record will probably not take a lot of time. It’s those record changes that tend to take longer.
Successful verification will get you to this screen
From this point on, you’ll be able to pick your domain name already in the user creation wizard.
Should you choose to continue, more DNS records will be added.
Skip forward to user creation. (link not yet implemented, because too lazy)
The screenshot above will give you a sneaky Microsoft question, with the default option set to “Set up my online services for me”.
Though Microsoft might say “Recommended”, I strongly disagree here.
“Why’s that”, you say ?
In case you decide to stop your O365 adventures and want to move on to a new platform for mail, you’re going to have to go through a lot of hassle to set this straight again.
Always choose to manage your own DNS records and click “Next”. Unless you’re REALLY pissed about your current DNS provider. In that case, I still suggest just finding another one. BUT NOT MICROSOFT FOR THE LOVE OF GOD.
Choose what you need (or select all)
A step that has been neatly added in the onboarding wizard, since Q4 of 2017 is the “Choose your Online Services” wizard.
This narrows down the amount of DNS records for you to add, according to the active checkmarks.
I’m going to select all of them, because I know my end-customer Oliver Shortstraw will need toe Exchange parts as well as the Mobile Device Management.
He’s also a somebody that changes his mind in the blink of an eye, so just to be sure we won’t have to setup anything else later, I also picked “Skype for Business”.
A somewhat huge list of DNS records will appear, for you to fill into your favorite DNS hoster *cough* OVH *cough*
A wild list appears. You crit it for 9000. It was super effective
Now in order to fully understand what’s going on here, I’ll explain in detail the actual stuff that’s going on. Teach a man to fish etc.
FINAL WARNING (I won’t repeat it again) DO NOT CHANGE THE MX RECORD JUST YET (unless this is a brand new setup for a brand new domain, then go ahead and have fun)
CNAME : autodiscover > autodiscover.outlook.com
This record basically tells your Outlook client to read a pre-made config file on a Microsoft server.
Thus allowing you to just enter your e-mail address and password in the Outlook setup wizard, instead of having to go through the hassle of manually setting up your O365 config.
CNAME : sip > sipdir.online.lync.com Refers to the actual SIP server for using Skype for Business/Lync/Teams. Your communication client will connect to this server and this server will in place patch you through to the geographically most redundant SIP server.
CNAME : lyncdiscover > webdir.online.lync.com
This server uses the same Autodiscover protocol as the Outlook one.
It patches you through to the correct Microsoft server cluster where your tenant is hosted, as well as other various kinky background processes. Dragons be here.
CNAME : enterpriseregistration > enterpriseregistration.windows.net
Basically serves as a registration server (duh), so the Microsoft servers know what mobile device was added to the tenant for so-called “conditional access”
CNAME : enterpriseenrollment > enterpriseenrollment.manage.microsoft.com
Enrolling (again, duh) Windows mobile devices and managing them through Microsoft Intune, requires these servers.
TXT : v=spf1 …
Specifies the server(s) that may send mail, originating from your domain name.
More on SPF records in an other post.
For now, follow the suggested entry, which – shortly explained – allows a group of servers that are defined in the name spf.protection.outlook.all to send mail from your domain. All others are denied.
SRV : _SIP
Together with the sipfederationtls entry, these are usually the more tricky ones to enter, depending on the DNS management tool. [An example from the one.com hosting panel].
This specific entry provides the security layer.
SRV : _SIPFEDERATIONTLS
This entry states the TCP port 5061 is being used for everything federation-related in communicating over SIP. A Classic SIP port uses port 5060. Microsoft likes to do things in their own special way…
MX : xxxx-yy.mail.protection.outlook.com
An automatically generated server name, based on your domain name and domain extension.
MX is short for Mail Exchanger and tells other mailservers in the world where to go dump its mail for your specific domain name.
The second you change this record in your DNS management (and it gets propagated world wide, bla bla) your mail will be directed to the server(s) in this record.
<lazy mode> Let’s assume for the time being, that our test company does not care much for just a little downtime and let’s change all these records in our DNS management tool </lazy mode>
Clicking the “Verify” button at the bottom of the wizard page will get Microsoft’s O365 server to check all your entries. Depending on the DNS management tool and the hosting company, this might take a couple of seconds up to a couple of hours.
After a successful verification of all entered services, let’s move on to creating new users in the next post.
For now, pat yourself on the back for a job well done and have a refreshing beverage.
Antique software ? No TLS/SSL support for outgoing mail ?
No problem !
If you stumble upon this article through a Google search (who uses Bing, anyway…), you’re probably wondering how to solve the following issue (or something similar) :
It’s all about the Pentiums, baby !
You have this old invoicing software that doesn’t get updates anymore ever since 2008 and relies on port 25 – unauthenticated – to send mails through your ISP’s outgoing mail server.
You happen to have this beautiful product called ‘Office 365’ and use its mail functionality for your own domain name. This domain name is used as outgoing mail domain in your software.
Luckily, you still have a Windows Server randomly lying about (hopefully 2008 R2 or higher, but this trick works with older stuff as well – also : this works on a Windows 7/8/10 , even though the IIS install method will be different)
Installing SMTP in IIS
2012 R2 Server Install Internet Information Services (IIS)
In Server Manager, select Add Roles.
On the Before you begin page in the Add Roles Wizard, select Next.
On the Select Installation Type page, select Role-based or Feature-based installation.
On the Select destination server page, choose Select a server from the server pool, and select the server that will be running SMTP services. Select Next.
On the Select Server Roles page, select Web Server (IIS), and then select Next. If a page that requests additional features is displayed, select Add Features and then select Next.
On the Select Role Services page, make sure that Basic Authentication under Security is selected, and then select Next.
On the Confirm Installation Steps page, select Install.
Install SMTP
Open Server Manager and select Add Roles and Features.
Select Server Selection and make sure that the server that will be running the SMTP server is selected and then select Features.
On the Select Features screen, choose SMTP Server. You may be prompted to install additional components. If that’s the case, select Add Required Features and select Next.
Select Install. After the installation is finished, you may have to start the SMTP service by using the Services snap-in for the Microsoft Management Console (MMC).
2008 R2 Server Install Internet Information Services (IIS)
In Server Manager, select Add Roles.
On the Before you begin page in the Add Roles Wizard, select Next.
On the Select Server Roles page, select Web Server (IIS) and select Install.
Select Next until you get to the Select Role Services page.
In addition to what is already selected, make sure that ODBC Logging, IIS Metabase Compatibility, and IIS 6 Management Console are selected and then select Next.
When you’re prompted to install IIS, select Install. You may need to restart the server after the installation is finished.Install SMTP
Open Server Manager and select Add Roles and Features.
On the Select Features screen, choose SMTP Server. You may be prompted to install additional components. If that’s the case, select Add Required Features and select Next.
Select Install. After the installation is finished, you may have to start the SMTP service by using the Services snap-in for the Microsoft Management Console (MMC).
Select Start > Administrative Tools > Internet Information Services (IIS) 6.0.
Expand the current server, right-click the SMTP Virtual Server, and then select Properties.
On the General tab, select Advanced > Add.
In the IP Address box, specify the address of the server that’s hosting the SMTP server.
In the Port box, enter 587 and select OK.
On the Access tab, do the following:
Select Authentication and make sure that Anonymous Access is selected.
Select Connection > Only the List Below, and then specify the IP addresses of the devices that will be connecting to the SMTP server, such as printers.
Select Relay > Only the List Below, and then specify the IP address of the devices relaying through this SMTP server
On the Delivery tab, select Outbound Security, and then do the following:
Select Basic Authentication.
Enter the credentials of the Office 365 user who you want to use to relay SMTP mail.
Select TLS Encryption.
Select Outbound Connections and in the TCP Port box, enter 587 and select OK.
Select Advanced and specify SMTP.office365.com as the Smart Host.
/!\ Restart the IIS service and the SMTP service. /!\
Actually testing, before applying
You can test SMTP relay services without using your software that needed it in the first place.
To test SMTP relay services, use the following steps.
Create a text file using Notepad or another text editor. The file should contain the following code. Replace the source and destination email addresses with the addresses you will use to relay SMTP.
FROM: <source email address>
TO: <destination email address>
SUBJECT: Test email
This is a test email sent from my SMTP server
Save the text file as Email.txt.
Copy the Email.txt file into the following folder: C:\InetPub\MailRoot\Pickup.
Try to copy it instead of just moving it. The mail file will disappear.
After a short time, the file should automatically be moved to the C:\InetPub\MailRoot\Queue folder. When the SMTP server delivers the mail, the file is automatically deleted from the local folder.
Warning: If the SMTP server can’t deliver the message, a non-delivery report (NDR) is created in the C:\InetPub\MailRoot\BadMail folder. You can use this NDR to diagnose delivery issues.
Troubleshooting
This is where most guides fall short.
Read the mails, that appear in the Badmail folder.Usually there will be a reason for refusal or non-delivery explained in these files.
If you have ‘show file extensions’ turned on, they will appear as .BAD files.
Open with Notepad or a similar pogram to see something like this :
Self-explanatory, I guess.
If mails were to actually arrive at their destinaton, but marked as “phishing” or appear in the spam folder of your recipient, chances are pretty high, your software package is still sending out through the wrong outgoing mailserver.
Seeing as I’m not a psychic, I can’t know how to configure outgoing mail in every piece of software.Press F1
An other reason for your mails being marked as “phising” (and I deliberately left this near the end of this article), is also related to the above (still sending out through your ISP’s SMTP server using an Office 365 mail address). HOWEVER…
When the mail arrives – even though its marked as spam – this means your ISP was able to actually deliver it. In Office 365 cases, this usually means that your ISP is not allowed to send out as your O365-linked domain name.
I’ll provide a detailed how-to on interpreting mail headers in a later post, but for the purpose of this exercise, let’s presume the mails are being marked because of the above.
In this case, just adding/editing an SPF record that relates to your ISP will be enough.
The somewhat attentive reader might be asking himself ‘if I could just add an SPF record using the records for my ISP, then why did I even bother reading this article ?
I’ll keep the answer very simple : EVERY user of this ISP will have the ability to send mail as your domain name, without passing some form of verification in this case.
AAaaaaand we’re back to the 80’s/90’s , where it was common fun and games to change your mail address in Outlook Express or other old mail software.
Random : Did you know that Outlook Express’ executable file msimn.exe was named, because it’s short for MicroSoft Internet Mail and News ?
Mail does not arrive and the NDR gives an authentication error :
Did you change your O365 password for the account that you use to authenticate for the SMTP connection ?
Yes you did. (or you just made a typo)
Mail does not arrive and the NDR gives a ‘does not permit to send as’ error :
Most often, this occurs when not sending as the account that is the SMTP relayer.
Your fancy 80’s software probably sends as (e.g., which is latin for exempli gratiā and is often translated as example given – just sayin’) invoicing@shortstraw.be, while your SMTP’er is oliver@shortstraw.be.
To solve this, either change your outgoing mail address in your 80’s software, change the authenticating O365 in your SMTP relay server OR…. *drumrolls* add ‘send as’ permissions to the invoicing mailbox for Oliver’s account.
What’s that ? invoicing@shortstraw.be does not exist in your O365 tenant ?
Yeah… I figured as much…
Add is as an alias to Oliver’s box or create a new box. Choice is yours.
Oh, and in a footnote : you will not find the mails sent through your relay’er in the resp. mailbox’ Sent Items.
Handy for troubleshooting… NOT
Before we start, I’d like to add a little disclaimer here, saying you can seriously mess up your mail folders if you just fiddle around without knowing what you’re doing in the software we’ll be using.
You didn’t think I was going to let you start a migration process without making you read the detailed “how and why”, did you ?
Once you’ve gotten hold of the PST files, there’s a couple of ways to get them in Office 365, but seeing as I already advised to stop your users from using their email for a while, you get to strike while the iron is still hot.
Windows users : Open Control Panel, go to Mail (32 bits or no reference to the number of bits, depending on the version).
Contacts icons)
If you’re born before 1990 (and if you’re in IT), you probably grew up with self-signed certificates.
Beautifully explained on 
The Exchange Admin Center is actually the way to go when you want to configure your mail environment in more detail.
In our example, Oliver had a couple of aliases in his old mail setup.
The above example was just a textbook sample provided by Microsoft to get you started. It should be sufficient for the average O365 setup.
One important icon you’ll see, is the “Admin“.
Open the Setup menu and click “Domains”
Install Internet Information Services (IIS)
Install Internet Information Services (IIS)
