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Connect-Up for Microsoft Outlook 365
Connect-Up for Microsoft Outlook 365
Angel Horowitz avatar
Written by Angel Horowitz
Updated over a week ago

Connect-Up for Microsoft Outlook 365

Syncing Appointments Between Two Calendars

  • Pricing Tier: All

  • Appointment Version: Single or Multiple Appointments per Time Slot

Connect-Up for Microsoft © Outlook 365 ® is the ideal solution for subscribers of both the DaySmart Appointments scheduling system and the Office 365 productivity suite. This plugin feature enables Staff Members to connect one of their Outlook 365 calendars with their DaySmart Appointments calendar.

Important Notes

  • DaySmart Appointments Events will not sync to Microsoft Outlook 365

  • All access types can use Connect-Up for Microsoft Outlook 365, but only Headquarters Administrators can enable the plugin from the Marketplace.

    • View-only users can view DaySmart Appointments Appointments in their Outlook 365 calendar, but cannot edit or cancel them. Additionally, since they cannot create Reserves, the 2-way sync from Outlook is not supported.

  • Each DaySmart Appointments profile can only sync with one Outlook calendar at a time.

  • Users can only sync to Outlook calendars they own. Outlook calendars shared with the user or with “read only” access cannot be synced.

  • Only items 90 days in the future will sync.

  • Depending on the default calendar increment setting in Outlook, Appointments may not be displayed proportionally for the user.

  • All-day meetings created in Outlook will not sync to your DaySmart Appointments calendar. To mark a day as completely unavailable, set the date as a Day Off for the Staff Member's profile.

Enabling the Plugin

As a Headquarters Administrator, you can enable this feature for your account or Location by visiting The Marketplace. This plugin is located in the Calendar Sync category. If you do not see this plugin in your account, please open a Support Ticket for assistance.

  1. Locate the Connect-Up for Microsoft Outlook 365 plugin.

  2. Click Enable.

  3. On the plugin’s description page, select one or more Locations from the drop-down menu.

  4. Click the Enable button.

Activating the Plugin for Staff Members

Once the plugin is enabled, users with the access type of either Headquarters Administrators or Location Administrators may choose to activate this feature for Staff Members in this account. From the plugin’s Settings tab, click on the Staff Members dropdown and select those users that you want to invite to connect their DaySmart Appointments calendar with their Outlook 365 calendar. Click Update Settings to save the settings.


Following this update, Staff Member profiles that contain an email address in their profile will be sent an email invitation to set up their DaySmart Appointments calendar and Outlook 365 calendar connection. The email will contain a link to complete this setup. They will need to have their DaySmart Appointments login and password handy for the next step.

Disconnect Staff Members

There are two ways for administrators to disconnect Staff Members. The first way Is from the Staff Members section of the application. When viewing the list of Staff Members in a Location, you will see the Connect-Up for Microsoft Outlook 365 column. Users will either be enabled or disabled. Change the setting for the appropriate user and click Update at the bottom of the page.

The second way is from the plugin’s Settings tab. Visit The Marketplace and access the Connect-Up for Microsoft Outlook 365 plugin from the left side. Click the Settings tab and, in the Staff Members tab, uncheck the user(s) who should no longer be able to sync their calendars. Update Settings once you have made appropriate changes. Any information synced between the calendars will then be removed and the connection severed.

Connecting to Microsoft Outlook 365

For users that are not administrators, you can connect and set up your synchronization to your Outlook 365 calendar. There are two ways you can connect your DaySmart Appointments calendar with your Outlook 365 calendar.

Sign In and Connect from Site Administration

If you are the logged-in Staff Member attempting to set up the calendar synchronization for yourself, these are the steps you will follow:

  1. Sign in to your DaySmart Appointments account.

  2. Click the Staff Members tab.

  3. Select your profile from the list.

  4. Click Connect-Up for Microsoft Outlook 365.

  5. If you aren’t currently signed in to Microsoft Office 365, you may be prompted to sign in with your Office 365 username and password.

    1. You may be prompted to enable access to your calendar data. Allow this connection to continue the setup. If you deny this connection, you will not be able to synchronize your calendar entries.


Connect from the Invitation Link

If you are an administrator logged in and managing the profile of a different Staff Member, you will only see the option to send an email invitation to the other Staff Member. This link does not indicate if the user has set up their sync.

Reminder to administrators: Users you activate will automatically be sent an email invitation.

  1. Open your email client and locate the email from the DaySmart Appointmentssystem.

  2. Click the link to join Connect-Up for Microsoft Outlook 365.

  3. If prompted, sign in with your Office 365 username and password.

    1. You may be prompted to enable access to your calendar data. Allow this connection to continue the setup. If you deny this connection, you will not be able to synchronize your calendar entries.

NOTE: Administrators cannot access the sync settings of other users.

Logging In to Connect-Up

The next step is to log in to the Connect-Up system. You will use your DaySmart Appointments credentials. Click Login to continue to the settings page.


Setting Up the Sync

Before starting the sync, you will determine how you want Appointments or Reserves from the DaySmart Appointments system to sync to your Outlook 365 calendar. Additionally, you can decide if and how meetings from Outlook 365 should sync to your DaySmart Appointments calendar.

  1. Select one Outlook 365 calendar from the drop-down menu with which you would like to sync.

  2. Review and, if needed, update the Contact Email address to which sync notification alerts should be sent.

    1. This will initially display the address associated with your DaySmart Appointments Staff Member profile. You may change this to any other email address you desire.

    2. It is recommended that this be the email address you check most frequently.

  3. Choose the following automated notifications:

    1. Notify when a resync is completed.

    2. Notify when an Appointment/Reserve cannot be updated from Outlook 365.

      1. When you receive this notification, it means that the Appointment or Reserve could not be moved due to another Appointment, Reserve, or Outlook meeting existing in the same time slot.

      2. The preference for overbooking DaySmart Appointments Appointments is supported in Single Appointments per Time Slot accounts only.

    3. Determine what items to sync between calendars:

      1. Sync DaySmart Appointments Reserves to Outlook 365

      2. Sync Outlook meetings to your DaySmart Appointments calendar

      3. Sync Outlook meeting details to your DaySmart Appointments calendar

        1. Note: This only applies to the body or description of the meeting. The title will still sync to the user's DaySmart Appointments calendar.

      4. Choose the Outlook meeting Show As options to sync to your DaySmart Appointments calendar:

        1. By default, Busy and Out of Office are selected.

        2. Any status selected will sync and block time on your DaySmart Appointments calendar as a Reserve.

      5. Click Start Sync.

        1. Note: After initial setup, if you return to this page, you’ll see a Resync button.


Changing the Sync Settings

From your DaySmart Appointments profile, click on the Connect-Up for Microsoft Outlook 365. Using your DaySmart Appointments account credentials, log in to view the current settings. To change settings:

  1. Click Disconnect Calendar.

  2. Confirm you wish to disconnect the calendars, which will remove items previously synched between the two calendars.

  3. After disconnecting, you will return to the setup page.

  4. Make the changes you need and Start Sync.

Syncing Appointment Details to Outlook

Once the two calendars are connected, you will be able to open and view DaySmart Appointments Appointments from your Outlook 365 calendar. When viewing the calendar item, any fields that contain information for the Appointment will display in the body of the Outlook meeting window. The calendar item will identify the entry as coming from the DaySmart Appointments (DA) system and display the Customer and Service name as the meeting title.

Handling Private Outlook Meetings

Outlook meetings set to Private will not sync the title or description to your DaySmart Appointments calendar. The title will default to Reserved. If an existing meeting that was previously synced to your DaySmart Appointments calendar is updated to private, the title and description will be removed.

Disconnecting from Outlook 365

Users can individually disconnect from the plugin at any time by clicking the Disconnect Calendar option in the Connect-Up for Microsoft Outlook 365 settings page. This will remove all Outlook meetings from your DaySmart Appointments calendar and all Appointments and Reserves from your Outlook calendar.


Note: Administrators may also disconnect calendars by removing Staff Members in the Settings tab of the plugin.

Resend Invite Email

At any time, Administrators have the ability to resend invitations to join Connect-up for Microsoft Outlook 365 to other users from the user’s staff profile. The email notification is sent to the email address associated with the user’s DaySmart Appointments profile. To resend the invitation:

  1. Sign in to your DaySmart Appointments account

  2. Click Staff Members

  3. Search for and locate the specific Staff Member. Click the link to access their profile.

  4. Once in the user’s profile, click Email invitation to join Connect-Up for Microsoft Outlook 365.

Note: The amount of time that the link is valid is based on your DaySmart Appointments account setting to automatically logout an idle user (Settings > General > Preference 10).

Disabling the Plugin

If you decide that you no longer want to use this feature, you can return to the Marketplace and remove the plugin from any or all Locations.

  1. Click Marketplace.

  2. In the left-hand column, find the plugin.

  3. On the plugin’s first tab, click the Locations drop-down field.

  4. Uncheck individual Locations or click None.

  5. Click Update.

Troubleshooting issues

How do I check which email address/calendar is set up to sync with my DaySmart Appointments calendar?

  • To verify the calendar address with which you are syncing, visit You may already be logged in and end up on the sync settings page. If so, locate the email address in the upper left corner of the application. This is the Microsoft account that is syncing with your DaySmart Appointments calendar.

Why is the email address in the Contact Email field different?

  • The Contact Email field in the main body of the Connect-Up settings page identified the email address at which you will receive notifications related to sync activity, like when a resync is completed or if an Appointment or Reserve cannot be moved by changing the date or time in your Outlook 365 calendar.

  • This may be different than the Microsoft account that is connected to for syncing. This Contact Email is simply the email address you check most frequently so that you are able to receive notifications from the sync system in a timely manner.

Why do Appointments on one calendar appear to be at a different time on the other calendar?

  • Check your timezone settings in your Outlook and DaySmart Appointments accounts. If both systems are not set to the same timezone, synced items may not show at the correct start time.

How do I sync Appointments from multiple DaySmart Appointments schedules to a single Outlook calendar?

  • Users cannot sync multiple DaySmart Appointments schedules to a single Outlook calendar. The error message: "There is another account already using this Outlook calendar. Please select another Outlook calendar." will show when attempting to add the same Outlook calendar to multiple DaySmart Appointments schedules.

What happens if my calendars are disconnected?

  • If your calendars become disconnected, you will receive an email at the email address set in step #2 with this status change. To reconnect and resync, follow the directions in this email message.

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