Install the Microsoft Outlook add-in


The Adobe Sign for Outlook add-in allows a user to configure a new agreement from within their email client by either composing a new email, starting from a blank slate, or by replying to an existing email, importing the recipient list, and automatically attaching any files from the source email.

This document is broken into three parts:

  • Installing/Enabling the add-in on your Outlook account – The one-time process for enabling the add-in from the 365 store. All users should be able to do this without elevated system permissions.
  • Establishing the authenticated connection between Outlook and Adobe Sign – Once the add-in is enabled, a trust relationship between Microsoft and Adobe Sign has to be created. This is done by authenticating to both environments, and only needs to be established one time.
  • Using the add-in – This section explores the features of the add-in and how you can use it to leverage Adobe Sign directly from your email client.

365 Admins can centrally install the add-in at the tenant level, and control access at the user level if desired.

Note: During authentication and use of the add-in, Outlook 365 will prompt an authorization panel when attempting to open a new window. When this happens, click Allow.


Supported products:

  • Exchange Online


  • Outlook 2013 (Windows v15+)
  • Outlook 2016 (Windows v16+)
  • Outlook Online – Using:
    • Chrome v59+
    • Firefox v53+
    • Safari 9+
    • Edge 38+
    • IE 11+
  • Outlook 2016 (Mac v15.35+)

You also need to comply with the basic Microsoft requirements to use Office

  • This add-in is not supported in mobile browsers and mobile apps
  • For the add-in to properly work, cookies must be enabled in the browser.
  • Use of the Desktop application requires that cookies be enabled in Internet Explorer.
  • Private/Incognito browser sessions are not supported.
  • Pop-up blockers must be disabled to use the automatic reply aspect of the Fill and Sign feature.

IE/Edge browsers

For the add-in to work seamlessly in Internet Explorer and Edge browsers, you must trust the below sites in your browser security configuration:

  • https://*
  • https://*
  • https://*
  • https://*
  • https://*
  • https://*
  • https://*
  • https://* (If using a Live account)
  • https://*
  • If using a third-party identity management system, that URL needs to be added as well

Mac High Sierra OS

High Sierra users may encounter an issue while trying to access the add-in from the Outlook desktop app (version 16.11 up) that throws a generic error message from Adobe Sign stating that the cookies are not enabled. 


If this happens:

  • Open the add-in Settings, and Sign Out
  • Re-authenticate to the service by clicking Get Started

If re-authenticating fails to correct the problem, contact customer support.

Enabling the add-in

The Adobe Sign for Outlook add-in can be installed in both the web based and desktop launched applications. Installing the application in one environment enables it in both

Access to the store is slightly different in each environment, and instructions are provided below for both. 

Installing the add-in for OWA (the web-based client)

1. Log in to your 365 Outlook account and select the Mail option

2. Click the gear icon in the upper-right corner of the screen

3. Select the Manage integrations option to load the Add-ins for Outlook page


4. In the top left search box, type Adobe Sign and click the search icon

5. To the right of the Adobe Sign for Outlook option, click the On button enable the integration

  • Once done, you should see Successfully added below the integration
OWA Add in store


6. Close the Add-ins page

To access the add-in, open any email. You will find the Adobe Sign icon in one of two places:

  • New emails – The interface to compose a new email exposes the icon in the lower-right corner of the screen
    • New emails only have the option to Send for Signature
OWA Icon Placment - N


  • Reply emails – When replying to an email, the icon is found in the upper, mid-right corner of the window (depending on how many add-ins you have installed)
OWA Icon - Reply


When you invoke the add-in from a Reply email, a pop-out menu will appear prompting you to select one of three functions (as described in Using the add-in section).

Installing the add-in for the desktop Outlook client

1. Open your desktop Outlook application

2. Navigate to the Home tab, and click the Store icon in the Add-ins section


If the Store button is not visible in your ribbon options, then it is likely that your Office admin has disallowed individual store access.

Contact your Office admin or IT team to allow access, or deploy the add-in to your organization.

3. In the top left search box, type Adobe and click the search icon

4. When you find the Adobe Sign for Outlook option, click the Add button to enable the add-in

  • Once done, you should see Added and a blue check indicating the add-in is available
Install Desktop

After enabling the add-in, you will find a new Adobe Sign section (with three icons) in your ribbon on the Home tab:

Establishing the authenticated relationship

Once the add-in is enabled within the email client, you must create a relationship between your Microsoft account, and your Adobe Sign account. This ensures that you, and only you, are sending agreements through your Adobe Sign user.

The configuration process is quick, and only requires that you know how to authenticate to the two systems. 


Once you have established this relationship, you do not need to authenticate again to either system. The authenticated relationship is persistent unless explicitly deleted by signing out of the add-in.


To establish the trust:

1. Click the New Email button as if you were composing a new email

2. Find the Adobe Sign icon in the email page layout and click the Send for Signature option

  • This opens the add-in panel on the right side of the window

3. Click the Get Started button in the add-in panel

  • The Get Free Trial link opens a new window to the Adobe Sign 30-day free trial registration page. If you don’t already have an Adobe Sign account, sign up for the free trial before you continue. No billing information is collected, and there is no commitment to pay anything during or after the trial.

4. You may be prompted to authenticate into the 365 environment. Click the user you intend to use. (The user you are already authenticated as will be at the top of the list)

5. Office 365 then prompts you to grant access to the add-in. Click Accept

A new window opens to capture the authentication for Adobe Sign.

6. Authenticate using your Adobe Sign credentials. 

OWA Auth to AdobeSign

7. After authentication to Adobe Sign, you are asked to confirm the access.  Click Allow Access

OWA Auth Verify to Adobe Sign

Once the Adobe Sign authentication is successful, the add-in panel on the right changes to show the add-in splash page.  Click Got It to open the configuration panel.

The trusted relationship is in place and will remain functional until you sign out of the add-in.

Disabling/uninstalling the add-in does not delete the trusted relationship. 

Using the add-in

With the trust relationship to Adobe Sign established, you can start sending agreements directly from your email client.

In the context of this add-in, Outlook has two modes:

  • Compose – Compose mode is anytime you can type/add to the email. This is generally achieved by clicking the New button, to start a new email, or the Reply button when replying to an existing email thread
    • When in compose mode, only the Send of Signature feature is available

  • Read – Read mode is any time you are viewing an email, but cannot edit/author it
    • Read mode enables three features:

1. Fill and Sign – A feature that allows the sender (and only the sender) to add content to, sign, and optionally send a file to another party as a completed document

2. Send for Signature – Creates an agreement that can have one or multiple recipients other than the sender. The sender may be a recipient, just not the only recipient

3. Agreement status – This option displays a list of the last ten agreements that include the user, including Draft, Out for Signature, Waiting for me to sign, and Signed

Sending from “Compose mode”

When launching the add-in from an email, the add-in seeks to include values from the email itself. Composing a new email (either from clicking the New or Reply button) allows you to configure that email as a template before launching the add-in, making short work of renewals, and other boilerplate transactions.

  • If an attachment is included in the email, the add-in attempts to attach that same file as the agreement document
  • If there are recipients listed in the TO: field (other than the sender), those emails will be imported as the recipient list, in the order they appear in the TO: field
  • If there is content in the Subject line, that literal string will be used as the Agreement Name.
  • If there is content in the body of the email, that content will be imported as the Agreement Message

All fields can be manually added to or edited. Importing values from the email is an optional perk, not a requirement.


At the top of the add-in panel is the Documents section. These are the files that are attached to the agreement, and presented to the recipients for their signature.

  • If you launch the add-in from an email with an attachment on it, that attachment is automatically inserted into the document list
  • If you want to remove a file from the Documents list, click the X on the far right of the document file name

Just to the right of the Documents heading is the + Add Files link that allows you to add files to the agreement.

  • The documents are presented to the recipients in the order they are listed in the add-in panel
  • If you need to add files from your Adobe Sign library, click the More Options link 

Supported file formats:

  • Word (.doc, .docx)
  • PowerPoint (.ppt, .pptx)
  • Excel (.xls, xlsx)
  • PDF
  • HTML
  • RTF


  • BMP
  • GIF
  • PNG

  • Recipients

    Under the Documents list is the Recipients list.

    The order that the recipients are listed in governs the order that the recipients will be asked to sign the agreement (in a sequential workflow).

    • If you launch the add-in from an email that has the TO: field configured, the recipients are imported to the add-in panel in the order they are listed in the TO: field
    • Recipients can be typed directly into the add-in panel
      • The panel will reference your Outlook contact list and attempt to match what you are typing to a known contact
    • All recipients have the role of Signer
      • If you need to set different recipient roles, or send using a parallel/hybrid workflow, click the More Options link
    • All signer verification Email.
      • If you need to use a second factor verification method, click the More Options link

    Agreement Name / Messages

    The Messages section is under the Recipients list.

    There are two fields in this section:

    The Agreement Name is the top field.

    • If you are launching the add-in panel from an existing or configured email, the Subject line is imported as the agreement name
    • If there is no Subject content, the name of the first attached (Document) file is inserted as the agreement name
    • The agreement name can be manually edited at any time

    The second field is the Agreement Message that is included in the Please Sign email.

    • When the agreement is launched from an existing email, the body content of the email is inserted into the message field
    • If there is no content in the email body, a default message is entered: Please review and complete this document.
    • The Message field as a 1000-character limit
    • In the top right corner of the Message section is a Clear Message link that will remove all the content from the Message window
    • If you use Message Templates or Private Messages, use the More Options link

    Preview & Send

    The Preview & Send checkbox invokes the Adobe Sign authoring environment once the Next button is clicked.

    • Checking the Preview & Send checkbox changes the text of the Send button to “Continue”
      • Unchecking the Preview & Send checkbox reverts the Continue button back to Send

    Send / Continue

    This button commits the agreement to the next step, either starting the signature cycle, or opening the authoring environment, depending on how the add-in panel is configured.

    The text of the button tells you what to expect:

    • Send – The Send button ends the configuration stage, and launches the agreement, notifying the first recipient.
    • Continue – When the Preview & Send checkbox is checked, the button text changes to Continue
      • Clicking the Continue button opens the Adobe Sign authoring environment where you can review the document order, and place form/signature fields as needed
      • After reviewing the document and/or placing any fields, the agreement is launched to the first recipient by clicking Send on the authoring page. You are not returned to the add-in to launch this agreement.

    More Options

    Adobe Sign offers a wider set of options than can reasonably be installed into an add-in. Features like recipient roles and private messages over complicate the relatively small footprint that the add-in occupies. But for many, those options are critical to the business process.

    The More Options link, just under the Send/Continue button, opens a windowed instance of the Adobe Sign Send page, complete with all options available to your account.

    All the configured elements in the add-in panel are imported to the Send page, in the order they exist, and they are fully editable if you need to make adjustments.

    Once the agreement is sent, the add-in panel presents a success notification.

    Two options are available in the post-send panel:

    • View Agreement – Opens a windowed view of the agreement that was just sent
    • Adobe Sign Menu – This option changes the panel to show the add-in feature options 
      • Send for Signature

    Additionally, a banner is added to the email body, indicating that the agreement is available to sign in a separate email.

    This is provided in the event that the sender wants to send a follow-up email to the one auto-generated by the Adobe Sign system.

    Post send email banner

    Sending from “Read mode”

    When reading an existing email thread, you have three feature options:

    • Fill and Sign – Used when you, and only you, need to fill in a document and apply a signature. No other signers are involved. If you get a request to “Fill this out, sign it and send it back to me”, this is the option you are looking for.
    • Send for Signature – The standard sending process for an agreement where the sender is not the sole signer
    • Agreement Status – Shows the status of the last ten agreements involving the user
    WA Icon - Reply

    Fill and Sign

    When the Fill and Sign option is selected, the attachment on the email (if any) is automatically attached to the agreement definition being built in the add-in panel on the right side of the window.

    Fill and Sign Start


    Just to the right of the Document heading is the + Add Files link that allows you to add more files to the agreement. Adding agreements works just like the web application. The documents are presented to the signer in the order they are listed in the add-in panel

    Fill and Sign add file


    Once all the files are attached, click the Continue button to launch the Fill and Sign window


    The Fill and Sign window allows you to:

    1. Type in text by clicking anywhere on the form and typing

    2. Place checks or solid dots (for check boxes)

    3. Apply your signature

    4. Apply your initials

    For more information on the Fill and Sign properties, check out this guide.

    When the document is completed, click the Done button in the upper-right corner.


    The document will process for a moment, and then open a Reply email with the signed copy of the document already attached.

    Fill and Sign post send

    The add-in panel will show a success message that you have signed the document, and present you with three options:

    • View Signed PDF – Opens a view of the signed PDF
    • Save a Copy – Downloads a copy of the signed PDF to your local system
    • Adobe Sign Menu – This option changes the panel to show the add-in feature options 
      • Fill and Sign
      • Send for Signature
      • Agreement Status

    Send for Signature

    1. When starting an agreement from an email with an attachment, notice that at top of the panel is the list of Document files currently “attached”.

    By default, any file that is attached to the email when the Send for Signature icon is clicked, is automatically attached.

    • Deleting that default file is perfectly fine.
    • Adding additional files is also permitted via the Add Files link


    2. Just below the Documents section, the Recipients are listed. Recipients are not imported from the email in Read mode.

    Click into the white field under the Recipients heading, and start typing either a name or email address. The add-in shows contacts from your 365 account that match the string you have typed in, helping to find the right recipient.

    The order that the recipients are entered dictate the signature order of the agreement (in a sequential signing process).

    Note: If you are accustomed to setting recipient roles, be aware that all recipients are considered Signers when configured in the add-in. If other roles are required, click the More Options link under the Send / Continue button.

    3. Under the Recipients list is the Message section, consisting of two fields.

    The top field is the Name of the agreement. By default, this field adopts the name value of the first file attached to the agreement. It can be manually changed to any value desired.

    The second field is the Message text. A default value is entered and can be edited freely.


    4. Just under the Message field is the optional Preview & Send checkbox. Checking this box opens a windowed version of the authoring page, exposing all the standard fields and tools for creating forms.

     The authoring page does not open until the Continue button is clicked.


    5. The Send / Continue button sends the agreement as currently configured.  If the Preview & Send check box is checked, the authoring page opens, allowing fields to be placed on the document.  Once all fields are placed, click the Send button at the bottom-right of the authoring page.


    6. Under the Send / Continue button is the More Options link. Clicking this link opens a windowed version of the Send page in the web application, exposing all the standard options that you would see in the application. Any configuration done in the add-in panel populates to the Send window, and is fully editable.

    All fields and options are available just as like the Send page in the web application, and any changes to the recipient or file list are included in the agreement.

    Scroll to the bottom of the window and click Next to enter authoring, or uncheck the Preview & Add Signature Fields box and click Send


    Once the agreement is sent, the add-in panel presents a success notification.

    Two options are available in the post-send panel:

    • View Agreement – Opens a windowed view of the agreement that was just sent
    • Adobe Sign Menu – This option changes the panel to show the add-in feature options 
      • Fill and Sign
      • Send for Signature
      • Agreement Status

    Agreement Status

    The Agreement Status option displays the last ten agreements (based on last update date) that are still open and waiting for some action. This includes drafts that are waiting for authoring, agreements waiting for your signature, and agreements waiting for some other recipient.


    Each listed agreement can be expanded to expose the most recent event posted for that agreement, indicating where in the signature process the agreement is.

    • The three most recent events logged against the agreement are listed (Created, Viewed, Signed, etc.), with the most recent on top
    • Clicking the View Agreement link within the agreement information opens a new window showing the document in its current state
    • Documents waiting for your signature display a Sign Agreement link that opens a new window containing the document ready to sign

    At the bottom of the events list is a Track All Agreements link that opens a windowed instance of the Manage page from the application. From the Manage page, the whole history of the account is available.

    Add-in Settings

    At the very bottom of the add-in panel, to the right of Adobe Document Cloud, is a gear icon that opens the add-in settings:

    Upgrade - Trial accounts only

    This link opens a new window to the Adobe Sign Upgrade process where you can purchase access to Adobe Sign on a monthly subscription.

    Sign Out – Breaking the authenticated relationship

    The relationship between your Outlook and Adobe Sign user accounts is “remembered” by the add-in, and this is why you don’t have to authenticate every time you use the add-in.

    However, it’s not uncommon for some users to send agreements from multiple Adobe Sign accounts.  This necessitates, that the user use the Sign out function to break the existing trusted relationship, and then establish a new relationship using the new Adobe Sign user account.

    To break the relationship, click the gear icon at the bottom-right of the add-in panel. A pop-up menu appears and the Sign Out option is at the top of that menu.


    A link to this guide and any additional built content regarding the add-in


    This will prompt a small pop-up that gives information regarding the add-in you are using.

    Privacy Policy

    This is a link to the Adobe privacy policy

    Installing at the Tenant level

    Installing at the tenant level allows the admin to expose the add-in by default, saving the users the installation steps, and ensuring that all users have access without issue.


    The below process enables the add-in at the tenant level for the whole user base. Check here if you would like more granular control over the deployment.

    The enablement is quick and easy, taking only about 5 minutes:

    1. Log in as the Tenant admin, and navigate to the Admin panel

    2. Go to the Exchange admin center

    3. Click the add-ins link

    4. Click the plus (+) to add a new add-in, and select Add from the Office Store option in the menu

    • The add-in installs as Disabled by default

    5. Configure the add-in

    • Assign Users
      • Everyone - Applies the deployment method to all users in the Tenant
      • Specific users/groups - Applies the deployment method to only the selected users or groups
      • Just me - Applies the deployment method to just the user (admin) doing the configuration
    • Deployment Method
      • Fixed (Default) - The add-in is automatically deployed to the assigned users and they are not allowed to remove it from their ribbon
      • Available -Users can install the add-in by clicking the Get More add-ins button on the home ribbon in Outlook
      • Optional - The add-in is automatically deployed to the assigned users, but they retain the option to remove it from their ribbon

    6. Click Save after selecting your enablement options

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