Communication

How do I set up text messaging (sms) for employees and families?

Employees

Under Administrative | Human Resources | Employees, you can open their profile. On the General tab, you first need to enter a cell phone and then select a carrier from the drop-down menu, Choose Carrier. Once you have that done, Update at the bottom.

Families

The contacts within the family will need to be set up for sms messaging. If you go into Back Office | Families and open their profile, go to the contacts tab. If a cell phone is not listed, click on the blue name and add the cell phone and Update. You will need to refresh the page for it to display. Next, click on the phone icon and choose a carrier from the drop-down menu, Choose Carrier. You will have the options to Save, Clear, Test or Close.

Students

For students, you will need to open the student's profile, General tab. Under the Student Information, you will need to put in the Cell and then Choose Carrier. Remember to hit the Update button at the bottom.

In the Recipient tab of a batch email, you have the following categories or groups you can use:

• Employee - Category - these are categories created and populated in Administrative| Human Resources| Categories

• Employee - Notification List - created in Communication| Messaging| Notification List| Employees tab.

• Contacts/ Parents - Category - created and populated in Address Book| Categories. See Email Categories

• Contacts/ Parents - Notification Lists - created in Communication| Messaging| Notification List| parents tab.

• Contacts/ Parents - Grade - select a grade level in order to select all parents who have a student in that grade level.

• Students - Grade - select students by grade level; the students need to have email addresses in their student profile.

• Students - Notification Lists - - created in Communication| Messaging| Notification List| students tab.

If my IMAP account is set up correctly, why do I sometimes get a red error message saying it is not?

Sometimes rather than seeing my Inbox, I see a red error message:

"Your IMAP account doesn't appear to be set up properly.

Go to Email/Accounts and select your account and confirm your settings with your ISP."

The Sycamore IMAP window is making a connection to your email server. That red message screen means we are trying to re-authenticate the connection to your email server and momentarily fail. Our system does not automatically ping the email server site to re-fresh, so if it is inactive for a period of time the connection may fail. You can fix this issue easily by re-freshing your screen (hit the F5 button).

How long does it usually take for emails to process?

Google's algorithm and sending times can be erratic sometimes, and it's not really something we can gauge, unfortunately.

The average is between 5 minutes and 24 hours, depending on the email size. There are factors that none of us can see, like how loaded Google's servers are.

Non-current families are included when pulling notification lists for batch texting/voice messaging.

There are 2 steps you need to complete at the beginning of each school year (it talks about this in Year End| Wrapping up steps):

1. Communication| Reports| Family Messaging, check all and Update to get everyone's messaging turned on.

2. Open Communication| Notification Lists| Parents| All Current count button, check all and Update.

This makes sure that all your current parents are included, and all non-current ones are cleared.

A DNS lookup of our SPF records would be the best way to obtain a complete list of our current IP's used for sending. As our IP's do change occasionally, it would be best to occasionally perform the DNS look-up of our SPF records to see if there are any configuration changes that you'll need to make.

You can perform a lookup of our DNS records at any time to obtain all of our current IP's with three `dig` commands:

Begin by doing a `dig` to find the Mailgun SPF record. For example:

$ dig -t TXT mailgun.org +short"mailru-verification: 78a0a835a374d20b""v=spf1 include:spf1.mailgun.org include:spf2.mailgun.org ~all"

Next, perform a `dig` for the value of each _include_ mechanism. For example:

$ dig -t ANY spf1.mailgun.org +short"v=spf1 ip4:173.193.210.32/27 ip4:50.23.218.192/27 ip4:174.37.226.64/27 ip4:208.43.239.136/30 ip4:50.23.215.176/30 ip4:184.173.105.0/24 ip4:184.173.153.0/24 ~all"$ dig -t ANY spf2.mailgun.org +short"v=spf1 ip4:209.61.151.0/24 ip4:166.78.68.0/22 ip4:198.61.254.0/23 ip4:192.237.158.0/23 ip4:23.253.182.0/24 ip4:23.253.183.0/24 ip4:104.130.96.0/28 ~all"

Alternatively, the website below can help you to obtain the same information. You'll enter the value of "mailgun.org" in the text box to see all the values with _include_ mechanisms. You will then query each value listed by an _include_ mechanism to see the results: http://www.kitterman.com/spf/validate.html

This indicates batch email has not yet been verified or is no longer configured.

Go to Communication | Batch Email | Drafts - Configuration.

Make sure that either Sparkpost or your school's mail server has been selected.

If you have credentials entered under the area where you are using your own mail server and the blue button 'Verify Account' is disiplaying, then you will want to make sure to get the account verified.

First, make sure that the credentials are correct. Click Update, (Be sure to update before clicking Verify.) Then, click Verify. If the credentials were entered correctly, then a date/timestamp will replace the blue Verify button.

If you get errors, check the following:

Server settings

Email address/Password

In gmail account (logged on directly)| settings (gear icon)| go to tab Forwarding and POP/IMAP, make sure IMAP is enabled

Allow Less secure apps - https://support.google.com/accounts/bin/answer.py?hl=en&answer=6010255

Turn off 2 step verification - https://support.google.com/accounts/answer/1064203?hl=en

Bounce status. This means the remote mail server (of the recipient) permanently rejects message. This may be a setting in place by their email provider. Bounced means that Sparkpost has made several attempts, but the email was not accepted by the provider. These families may need to see about whitelisting your sending domain so that they can receive the email from the school. The service they are using normally has instructions online about whitelisting. Sometimes bounces are because the recipient is on a suppression list, and we can sometimes help with that.

Queued status. This means that Sparkpost is still in the process of sending them. These aren't necessarily undelivered or non-sending. Queued simply means that the messages are waiting in a sending pipeline for the opportunity to send out. SP may have paused sending to that email provider address for spam protection purposes (they only send so many at a time). It could also have to do with the number of messages being sent to certain email providers. Sparkpost will continue to attempt delivery. Queued status will change to sent or bounced, etc. depending on if they get through.

If the emails are marked as Queued, it is actually possible that the emails were sent/delivered, but the server has not yet sent back the message to update the status in Sycamore. It can take 24 to 48 hours for the status to update in Sycamore.

Another reason could be because the number of emails sent out has reached the daily limit in gmail, Gmail does have sending limits.

Check for spaces at the end of the email addresses.

Make sure there are not a comma where a period should be.

Make sure contacts do not have multiple email addresses entered on their profile. There can only be one and that one goes in the first email box.

It will stay as queued if the recipient's email Inbox if full, if mailbox is unavailable, if user doesn't exist or email is over quota.

Make sure you have allowed popups in the browser for app.sycamoreleaf.com.

When clicking to Submit the email, be sure to not leave the batch email area until it is 100% complete. This means not leaving to go to another area of Sycamore or another tab in the browser.

If an email is canceled, it will show is Sparkpost as Campaign Canceled and will stop sending. Copy email and send to the ones that bounced.

If the receiving email address is tied to your school's domain, then you will want to check your Google Admin to see what may be preventing the emails from going through. There may be a rule in place that does not allow emails through that are outside of your domain.

When a school uses their own domain to send out batch email communication, it is tied to an email address and the password for that account. Normally when emails all of a sudden stop sending, it is because a password has been changed.

Go to Communication | Batch Email | Drafts | re-enter the password for the sending email address and Update. Click on the red trash can to delete the old verification and then click on the blue Verify Account button. Once a date and time stamp appear, the account will be re-verified and batch emails should send out again.

Troubleshooting

Here is a list of things you can check if you are getting an SMTP or IMAP error.

1. Does this individual still have an active account in your domain? If so, has there been a password change?

1. Has your domain changed? Your domains in HR and batch email should match. Note: The system doesn't support SMTP on multiple domains.

2. Also, if there has been a domain change in the Google Admin console, you may need to click a few verify buttons in a set-up screen in Google.

3. If there are multiple email accounts under Email | Accounts that are marked as Primary, then ideally you should remove one and only have one as primary.

4. If the verification date/time stamp hasn't been updated lately, you may want to update it. To do this, click on the red trash can to remove the verification. Provided the username and password are correct, click on the blue Verify button. If all goes well, a new date/time stamp should appear.

5. Make sure the email address being used has not been de-activated.

6. If your email server times out when sending, which it will if you click Send Now again before your connection with the email server is established, you will get an SMTP error message.

More Common Issues:

1. Make sure the password entered in the Account profile is the correct one. It should be the same one that lets you log into Gmail directly.

2. In Gmail account (logged on directly)| Settings (gear icon)| go to tab Forwarding and POP/IMAP, make sure IMAP is enabled. (don't forget to scroll to bottom to select Save)

3. In Gmail account, click on the icon at top right (With pic or Letter, might say g-suite) , click on Manage your Google Account| then on the left click Security | In the "Less Secure Apps" Section, make sure this is set "Allow less secure apps" to ON.
   NOTE: If in the "Signing into Google" section, 2-step verification is ON you will need to create an App specific password to use in Step 1 above. See this help article: https://support.google.com/accounts/answer/185833?hl=en

4. Visit http://www.google.com/accounts/DisplayUnlockCaptcha and sign in with your Gmail username and password. If asked, enter the letters in the distorted picture. At the "Allow Access to your Google Account" window, click Continue.

5. If the account was set up in Sycamore before IMAP was allowed, fully remove the Email Account in Sycamore and create it again.
   

Also, if you are the Admin person for Google, you can make sure IMAP is turned on for all, and that the Less Secure Apps is turned on for all. Here are help pages for that:

Less secure for all staff:

https://support.google.com/a/answer/6260879?hl=en

Allow users to allow less secure apps

IMAP for all staff:

https://support.google.com/a/answer/105694?hl=en

If your school has a new subdomain, you will want to be sure that the setup has been completed in the Google Admin console (click verify buttons in a set up screen in Google to see green check marks in the Google Admin screen.)

Updating a contact's cell phone number on their contact profile will not automatically update on the Notification List(s).

Follow these steps to get the notification list(s) updated:

1. Go to Communication | Reports - Employee Messaging/Family Messaging.

2. Check off contact's name.

3. Click Enable.

You can also select the cell phone number under the Messaging button of the family profile | Contacts. However, this may cause the contact to not list alphabetically on the Notification List.

If you are using SMS text messaging, you will need to go under the Messaging button to select the cell phone # and carrier in order for the SMS email to be updated.

For Batch Email, we automatically ask for a read receipt. Those read receipts that come back will change the status on the Recipient list from a closed to opened envelope. But again, the fact that the envelope is closed does not mean that parents haven't opened and read the email. It just means their isp or email server rejected the receipt request and didn't send anything back to confirm.

For the IMAP email, when composing an email, in the Gear icon drop down menu there is a Return receipt: checkbox. However, many ISP and email clients (including Outlook) give users the ability to block all read receipts/requests, so that ends up not being a very useful tool.

Microsoft Word appears the way it does because of all kinds of proprierary html code that is specific to Word. So when you try to bring that into a more basic editor, like what is in Sycamore, what you see is likely not what you get. If you were to have the the email open in Sycamore and go to Tools| Source Code, you will see a lot of MS specific html code.

Because of this, if you have to create a document/email outside of Sycamore, you will want to copy and paste it into a plain text editor like Notepad, then do the editing in the text once it is in Sycamore.

SMS Text Messages are converted to an email address, which consist of the cell phone number and the cell phone provider (e.g. Verizon 9999999999@vtext.com). These emails are sent out in batches just like a regular batch email. These are not instant because between Sparkpost and the parents' cell and email providers, the process has to go in small packets, so that it won't get marked as spam. With a true text service, such as Twilio, the messages will be almost instant, since it isn't having to send the message as an email, but rather, it is an actual phone text message (phone to phone).

Per Sparkpost:

"School domains can be particularly tricky, as they are often older, and have very specific anti-spam/virus software. Thus, they may be waiting to accept your emails. We always try to deliver for up to 72 hours. However, it is up to the recipient's email server as to if or when they want to accept them. As well, if you're sending on their behalf, that can look suspiciously like spamming, since their own domain appears to be coming from elsewhere. If that is the case, I recommend asking them to whitelist sparkpostmail.com, as well."

We also recommend whitelisting spmailtechnol.com.

Do we need to setup an SPF record since some users are not getting our Batch Emails, Notifications or SMS Text Messages?

Yes, you should setup an SPF record: Here is what an SPF record is and the addresses you need to use.

Sender Policy Framework (SPF) is an email validation system designed to prevent email spam by detecting email spoofing, a common vulnerability, by verifying sender IP addresses. SPF allows administrators to specify which hosts are allowed to send mail from a given domain by creating a specific SPF record (or TXT record) in the Domain Name System (DNS). Mail exchangers use the DNS to check that mail from a given domain is being sent by a host sanctioned by that domain's administrators.

In Layman's terms, if an email is sent from Sycamore, when not using your configuration in batch email but ours, then it is being sent by servers other than your mail server. So these emails can be determined as SPAM or Spoofed messages. Wherever your domain is registered, (Network Solutions, Tucows, SimpleURL, BulkRegister, or GoDaddy are some examples), you will need to create an SPF record for your domain with the IP's and domains listed below. At the bottom of this FAQ are some tools you can use and some examples of the text needed for the SPF record.

By creating an SPF record you are authorizing these IP addresses / domains below as legitimate senders of emails from your school.

sycamoreleaf.com

sender1.sycamoreleaf.com

198.101.162.34

166.78.78.159

23.253.198.96

198.61.244.55

23.253.198.97

23.253.198.100

23.253.198.98

23.253.198.99

198.101.162.36

Here is a good tool you can use to check your SPF record, as well as a tool to validate your text you will be entering in your SPF record. //www.kitterman.com/spf/validate.html

In the Host (Domain) section, enter your domain: yourdomain.com

If TTL(Seconds) 86400

Type IN TXT

Text: Text will look similar to this:v=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:198.101.162.38 ip4:198.101.162.39 ip4:198.101.164.68 ip4:198.101.164.69 ip4:198.101.164.70 ip4:198.101.164.175 ip4:198.101.162.36 ip4:198.61.244.52 -all

Validate: SPF (important)

When you verify the text with the above tool you should get something like this:

Input accepted, querying now...evaluatingv=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

SPF record passed validation test with pySPF (Python SPF library)!

When you verify your domain, you should get something like this:

SPF records are primarily published in DNS as TXT records.

The TXT records found for your domain are:v=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

SPF records should also be published in DNS as type SPF records.

No type SPF records found.

Checking to see if there is a valid SPF record.

Found v=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

evaluating...SPF record passed validation test with pySPF (Python SPF library)!

If there is a problem you may see this:

SPF records are primarily published in DNS as TXT records.

The TXT records found for your domain are:

v=spf1 include:_spf.google.com ~all

v=spf1 ip4:198.101.162.34

SPF records should also be published in DNS as type SPF records.

No type SPF records found.

Checking to see if there is a valid SPF record.

Results - Permanent Error Two or more type TXT spf records found.

No valid SPF record found of either type TXT or type SPF.

Lastly, if no SPF record is setup, you should see something like this:

SPF records are published in DNS as TXT records. No TXT records found for your domain.

SPF records should also be published in DNS as type SPF records.

No type SPF records found.

Some Additional Tools:

This tool can help you build your SPF record Text //www.mtgsy.net/dns/spfwizard.php

Fill Out This Section: Include IP addresses of any other hosts that send email for your domain.

Enter the IP addresses listed above.

Check Yes to this question: Does the above describe all the hosts that send mail for your domain?

Generate SPF record

This tool validates the code verses the policy: //www.vamsoft.com/spfvalidator.asp

Example:

v=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

If Staff with school domain email addresses are not receiving the batch emails:

You may have to change your domain settings to allow those emails to go through. Here is Microsoft FAQ to help with this:

https://technet.microsoft.com/en-us/library/dn198251%28v=exchg.150%29.aspx

For Office 365, go to Outlook Web App (http://mail.office365.com/owa), click Settings > click Options > Click Block or allow.

We have Exchange 2010 and 2007, we can't authenticate using our SMTP for batch email, help?

Here's the recipe for Exchange 2010 to work with Sycamore. It should also work with Exchange 2007. THESE SHOULD BE RUN BY YOUR EXCHANGE ADMINISTRATOR. These are power shell commands; the gui is very convoluted; these four commands should get you running. This creates an authenticated relay connector that only the Batch Email configuration email address (e.g. "sycamore@yourdomain.com") user can use. No other account can send via this relay; outside of the organization. The blessed Sycamore user can send as anyone to anyone from anyone.

The basics are:

1) Run 4 commands in the Exchange 2010 power shell.

2) Forward a port on your firewall

3) Restrict the port if you like to sycamore address at either the firewall or the exchange server.

4) In Exchange create an email user called "sycamore@yourdomain.com" and give it a password. NOTE - It is a good practice to use a general address such as Sycamore@yourdomain.com so that this process won't affect any individual's email account. This is the same email address with credentials you will use in Communication| Batch Email | Configuration.

Variables

RED values should be correct ones for your server.

BLUE is optional if you want to enforce TLS. It does requires a real SSL certificate "not-self signed".

GREEN is the custom port number you want to use.

ORANGE leave as is to allow any IP address to connect; or common separate list of sycamore sending servers.

You should use a port number other than 25. If you want to use 25 then you must restrict Orange -RemoteIP Ranges or the connector will not be unique and it will not be created.

Powershell commands:

[PS] C:>New-ReceiveConnector -Name SycamoreRelay -usage Custom -Bindings '0.0.0.0:61025' -fqdn YOUR-EXTERNAL-MAIL-SERVER-DNS-NAME -RemoteIPRanges '0.0.0.0-255.255.255.255' -AuthMechanism TLS,BasicAuth,BasicAuthRequireTLS -server NAME-OF-YOUR-SERVER-INTERNALLY -permissiongroups ExchangeUsers

[PS] C:>Get-ReceiveConnector SycamoreRelay | Add-ADPermission -User "sycamore@yourdomain.com" -ExtendedRights "ms-Exch-SMTP-Accept-Any-Recipient"

[PS] C:>Get-ReceiveConnector SycamoreRelay | Add-ADPermission -User "sycamore@yourdomain.com" -ExtendedRights "ms-Exch-SMTP-Accept-Authoritative-Domain-Sender"

[PS] C:>Get-ReceiveConnector SycamoreRelay | Add-ADPermission -User "sycamore@yourdomain.com" -ExtendedRights "ms-Exch-SMTP-Accept-Any-Sender"

Since there are specific domains that aren't getting our email, should I create an SPF record?

Yes, you should setup an SPF record: Here is what an SPF record is and the addresses you need to use?

Sender Policy Framework (SPF) is an email validation system designed to prevent email spam by detecting email spoofing, a common vulnerability, by verifying sender IP addresses. SPF allows administrators to specify which hosts are allowed to send mail from a given domain by creating a specific SPF record (or TXT record) in the Domain Name System (DNS). Mail exchangers use the DNS to check that mail from a given domain is being sent by a host sanctioned by that domain's administrators.

In Layman's terms, if an email is sent from Sycamore, when not using your configuration in batch email but ours, then it is being sent by servers other than your mail server. So these emails can be determined as SPAM or Spoofed messages. Wherever your domain is registered, (Network Solutions, Tucows, SimpleURL, BulkRegister, or GoDaddy are some examples), you will need to create an SPF record for your domain with the IP's and domains listed below. At the bottom of this FAQ are some tools you can use and some examples of the text needed for the SPF record.

By creating an SPF record you are authorizing these IP addresses / domains below as legitimate senders of emails from your school.

sycamoreleaf.com

sender1.sycamoreleaf.com

198.101.162.34

166.78.78.159

23.253.198.96

198.61.244.55

23.253.198.97

23.253.198.100

23.253.198.98

23.253.198.99

198.101.162.36

Here is a good tool you can use to check your SPF record, as well as a tool to validate your text you will be entering in your SPF record. //www.kitterman.com/spf/validate.html

In the Host (Domain) section, enter your domain: yourdomain.com

If TTL(Seconds) 86400

Type IN TXT

Text: Text will look similar to this:v=spf1 a mx ptr a:sender1.sycamoreleaf.comip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

Validate: SPF (important)

When you verify the text with the above tool you should get something like this:

Input accepted, querying now...evaluatingv=spf1 a mx ptr a:sender1.sycamoreleaf.comip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

SPF record passed validation test with pySPF (Python SPF library)!

When you verify your domain, you should get something like this:

SPF records are primarily published in DNS as TXT records.

The TXT records found for your domain are:v=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

SPF records should also be published in DNS as type SPF records.

No type SPF records found.

Checking to see if there is a valid SPF record.

Found v=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

evaluating...SPF record passed validation test with pySPF (Python SPF library)!

If there is a problem you may see this:

SPF records are primarily published in DNS as TXT records.

The TXT records found for your domain are:

v=spf1 include:_spf.google.com ~all

v=spf1 ip4:198.101.162.34

SPF records should also be published in DNS as type SPF records.

No type SPF records found.

Checking to see if there is a valid SPF record.

Results - Permanent Error Two or more type TXT spf records found.

No valid SPF record found of either type TXT or type SPF.

Lastly, if no SPF record is setup, you should see something like this:

SPF records are published in DNS as TXT records. No TXT records found for your domain.

SPF records should also be published in DNS as type SPF records.

No type SPF records found.

Some Additional Tools:

This tool can help you build your SPF record Text //www.mtgsy.net/dns/spfwizard.php

Fill Out This Section: Include IP addresses of any other hosts that send email for your domain.

Enter the IP addresses listed above.

Check Yes to this question: Does the above describe all the hosts that send mail for your domain?

Generate SPF record

This tool validates the code verses the policy: //www.vamsoft.com/spfvalidator.asp

Example:

v=spf1 a mx ptr a:sender1.sycamoreleaf.com ip4:198.101.162.34 ip4:166.78.78.159 ip4:23.253.198.96 ip4:198.61.244.55 ip4:23.253.198.97 ip4:23.253.198.100 ip4:23.253.198.98 ip4:23.253.198.99 ip4:198.101.162.36 -all

When sending a batch email, how do I send to a specific group of contacts?

First you need to set up a category for the group you want. Go to Address Book>Categories>New Category button. Give your category a name and Add (Groups are used to organize your list of categories).

There are 2 ways of adding people to the category.

1. In the Address Book>Categories click on the blue link (name) to open it. There will be a blue rectangular button with a "0" in it (next to "Count"). Click on it and a new window will open. Check the families you want to include in the category.

2. Go to Administrative>Back Office>Reports>Parent Categorizer. Select Current or All families; choose the category you want to apply; Choose the parent group you want to add it to (may need to do this for more than one group); Use the blue check mark to select all of the contacts; Click on the Add to Category button.

Once all the people are added to a category, you can then go to Administrative>Communication>Batch Email. In a new batch email there is a drop-down menu after Send To "Select Contact Category" where you can choose the category you created.

You will want to make sure that the user has been enabled for messaging. This can be done from the student, employee and family profiles.

You can also use the Family Messaging and Employee Messaging reports under Communication | Reports to enable messaging.

Once this is done, you can go to the Notification List to check off the user's name. Then Update.