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How Do You Encrypt an Email in Outlook, Gmail, and Office 365

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🔑 Key Takeaways

  • Modern Outlook uses Purview from the Encrypt ribbon. Outlook 2013 and older still route via S/MIME.
  • Personal Gmail has only Confidential Mode. Workspace Enterprise adds hosted S/MIME for true E2E.
  • Attachments inherit message encryption, or lock the file first with Acrobat, Word, or 7-Zip AES-256.
  • Office 365 Encrypt needs Business Standard or higher plus Azure Rights Management on the tenant.
  • A gateway skips per-user certs, works from Gmail or Outlook, and ships a BAA in the base plan.

Encrypting an email is a different set of steps in every mail client. Outlook has a button. Gmail has two paths that look similar but work differently. Outlook 2013 uses an older S/MIME workflow. Attachment encryption is its own separate topic.

This guide covers each of them in order. It also flags the HIPAA implications for practices sending PHI. For a cross-client path that works uniformly, a gateway service delivers encrypted email to any recipient without version dependencies.

Every section stands on its own with the menu paths named directly. Skip to the client and version that matches your setup.

Encrypt an Email in Modern Outlook on Microsoft 365

Modern Outlook on Business Standard and above adds an Encrypt button to the compose window. The service is Microsoft Purview Message Encryption.

Open Outlook. Start a new message. Click the Options tab in the ribbon. Click Encrypt. Choose Encrypt-Only or Do Not Forward from the dropdown.

Write the message and click Send. The recipient receives an email with a link. They authenticate with Microsoft, Google, or a one-time passcode and read the message in a browser.

Business Basic tier and free personal Outlook.com do not have the Encrypt button. Related linked topic: how do you encrypt emails for a broader coverage of alternatives.

Encrypt an Email in Outlook 2013 With S/MIME

Outlook 2013 supports S/MIME natively but has no Purview Encrypt button. The workflow uses the Trust Center and a client-installed certificate.

Install an S/MIME certificate in the Windows personal certificate store. Open Outlook. Go to File, Options, Trust Center, Trust Center Settings, Email Security.

Under Encrypted email, click Settings. Pick your signing certificate and your encryption certificate. Choose whether to sign or encrypt by default. Click OK.

To encrypt a single message, click the encrypt icon in the compose ribbon before sending. Recipients need S/MIME support in their client and a cached copy of your public key. This workflow also applies to Outlook 2016, 2019, and Outlook LTSC 2021 when S/MIME is the chosen path.

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Encrypt an Email in Gmail With Confidential Mode

Gmail confidential mode is available on all Google Workspace tiers and personal Gmail. Click the lock and clock icon at the bottom of the compose window.

Set an expiration date from the dropdown. Choose whether to require a passcode. Passcode by SMS is the higher-security option. Click Save.

Write the message and click Send. The recipient receives a link. They open it in a browser, enter the passcode if required, and read the message in a hosted view.

Confidential mode is not end-to-end encryption. Google holds the keys. The mode prevents forwarding, copying, and printing. It does not seal the content against the provider. For HIPAA-scoped mail, confidential mode alone is not sufficient.

Encrypt an Email in Gmail With Hosted S/MIME

Hosted S/MIME is the Gmail path to true end-to-end encryption. It requires Google Workspace Enterprise Standard, Enterprise Plus, Education Standard, or Education Plus.

The admin uploads root and intermediate CA certificates in the Google Admin console under Apps, Google Workspace, Gmail, User Settings, then S/MIME. Enable S/MIME for the organizational unit.

Each user uploads their personal certificate through Gmail settings under Accounts. Once configured, a lock icon appears next to the recipient field. Green means encryption is possible.

Recipients on personal Gmail, Business Standard, or Business Plus cannot receive hosted S/MIME messages. The encrypted content arrives as an unopenable attachment. See Google Workspace admin help for the current tier list.

Example

A physical therapy clinic on Microsoft 365 Business Premium builds an automatic DLP rule in the Purview compliance portal. The rule matches the US HIPAA template and triggers when outbound messages contain MRN patterns or SSN patterns. Action: apply Do Not Forward automatically. A new hire forgets to click Encrypt when replying to an insurance verifier and pastes a partial MRN into the body. The DLP rule fires server-side, encrypts the message, and creates an audit log entry the compliance officer reviews weekly.

Encrypt an Email Attachment for Extra Protection

The attachment inherits the encryption of the message when sent through Outlook Encrypt, S/MIME, or a portal gateway. This is sufficient for most cases.

For extra protection, encrypt the file itself before attaching. This adds a second layer that survives even if the message encryption fails or the recipient forwards the message to an unencrypted inbox.

Common attachment encryption tools:

  • Adobe Acrobat for PDF password protection with AES-256
  • Microsoft Word, Excel, PowerPoint via File, Info, Protect Document, Encrypt with Password
  • 7-Zip for archive password protection with AES-256
  • Apple Preview for basic PDF password protection on macOS

Share the password out of band by phone or text, never in the same email chain. Verify recipient identity before releasing the password. Related linked topic: encrypt an email.

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Encrypt an Email in Office 365 With Automatic DLP Rules

Office 365 supports automatic encryption through Data Loss Prevention rules on Business Premium and Enterprise tiers. This removes the human step of clicking Encrypt.

The admin opens the Microsoft Purview compliance portal. Under Data Loss Prevention, create a new policy. Choose a template for U.S. Health Insurance Act (HIPAA) or a custom policy with SSN, MRN, or ICD patterns.

Configure the action. Apply Do Not Forward, Encrypt-Only, or a custom rights template when a match is found. The policy can also block the send or require justification.

Automatic DLP encryption reduces the risk of staff forgetting to click Encrypt on a sensitive message. It also creates audit trail evidence that the covered entity applied technical safeguards under the HHS Security Rule.

Encrypt an Email With PGP Using FlowCrypt

FlowCrypt is a browser extension that adds PGP support to Gmail. It works on personal Gmail and any Google Workspace tier.

Install the extension from the Chrome or Firefox web store. Create a keypair when prompted. Back up the private key to a hardware token or an encrypted vault.

Send a secure message from the FlowCrypt compose window inside Gmail. The extension encrypts the body with the recipient public key if it is in the FlowCrypt cache. If not, the extension prompts for the recipient key or sends through the FlowCrypt password-protected fallback.

PGP is not native to any major business mail workflow. FlowCrypt fills that gap for teams that want end-to-end encryption without moving to Google Workspace Enterprise. It is not commonly used in regulated healthcare settings.

💡Pro Tip: Automate PHI encryption through DLP rules, never rely on manual clicks

Staff forget to click Encrypt on sensitive messages, especially during busy scheduling windows or shift handoffs. A single missed click is a HIPAA breach. Configure DLP rules in the Microsoft Purview compliance portal or Google Workspace Data Loss Prevention to match SSN, MRN, ICD-10, and custom keyword patterns. Apply Encrypt or Do Not Forward automatically when a match is found. This removes the human factor from compliance and creates audit trail evidence during OCR investigations.

Encrypted Email Options Compared

The table below compares the main paths a business considers.

Method Client Support Recipient Setup End-to-End HIPAA Fit
Outlook Encrypt (Purview) M365 Business Standard+ Passcode or SSO No, portal Yes with BAA
Outlook S/MIME Outlook 2013+ Certificate install Yes Peer traffic
Gmail confidential mode All Workspace Passcode No Not sufficient alone
Gmail hosted S/MIME Workspace Enterprise+ Certificate install Yes Yes
FlowCrypt PGP Gmail via extension PGP key exchange Yes Rare in healthcare
Gateway (Mailhippo) Any provider Passcode Portal-based Yes with base plan BAA

HIPAA Notes on Encrypting Email in Practice

Encryption is one technical safeguard among many. HIPAA requires access controls, audit logging, session timeouts, workforce training, and a signed BAA with each business associate.

Automatic DLP triggers reduce the risk of missed manual encryption. Portal delivery removes the recipient-side certificate requirement. Both are practical for a real HIPAA workflow.

Verify recipient identity before sending PHI. A wrong email address is a HIPAA breach even when the message is encrypted. Document policies and train staff. See related healthcare security features context.

Retention matters. Encrypted mail counts as PHI storage. Retention policies must match state medical board rules and the six-year HIPAA administrative retention requirement.

When a Gateway Is the Better Fit

Managing S/MIME certificates across a small team is meaningful operational work. Certificate expiration, mobile provisioning, and cross-platform trust chains all take time.

A gateway service removes the certificate step. The sender writes in the normal client. A trigger word or plugin button triggers encryption. The recipient reads in a browser.

Mailhippo works this way on top of Gmail or Outlook. It includes a BAA in the base plan. It works uniformly on desktop and mobile without version dependencies. See related how to encrypt an email for the broader walkthrough. Practices building a compliant public-facing site can pair this with HIPAA-conscious website design so intake, contact, and email flows stay inside the same compliance boundary.

Frequently Asked Questions

How do you encrypt an email in Outlook? +

On Microsoft 365 Business Standard and above, open a new message and click the Options tab in the ribbon. Click Encrypt. Choose Encrypt-Only or Do Not Forward. Write and Send. The recipient receives a link and authenticates with Microsoft, Google, or a one-time passcode. On older Outlook versions with S/MIME, install a certificate through the Trust Center under Email Security, then click the encrypt icon in the compose window before sending. The two paths produce different recipient experiences.

How do you encrypt an email in Gmail? +

Click the lock and clock icon at the bottom of the compose window for confidential mode. Set expiration and passcode. Write and Send. This is not end-to-end encryption. For true end-to-end on Google Workspace Enterprise, the admin configures hosted S/MIME and each user uploads a personal certificate. A lock icon then appears next to the recipient field. Green means encryption is possible. For personal Gmail, install a plugin like FlowCrypt to add PGP support. Confidential mode alone is not HIPAA-appropriate.

How do you encrypt an email attachment? +

The attachment inherits the encryption of the message when sent through Outlook Encrypt, S/MIME, or a portal gateway. For separate protection, encrypt the file before attaching. Open the PDF in Adobe Acrobat, choose Protect, set a password. Open the docx in Word, choose File, Info, Protect Document, Encrypt with Password. For archives, use 7-Zip with AES-256. Share the password out of band by phone or text, never in the same email chain. Verify recipient identity before releasing the password.

How do you encrypt an email in Office 365? +

Open Outlook on desktop, mobile, or the web. Start a new message. Click Options in the ribbon. Click Encrypt. Choose Encrypt-Only or Do Not Forward. Write and Send. The Encrypt button is available on Business Standard, Business Premium, Enterprise E3, Enterprise E5, and Government plans. Admins configure encryption templates in the Microsoft Purview compliance portal. Automatic encryption through DLP rules is available on Business Premium and Enterprise plans, which triggers Encrypt when messages match sensitive data patterns like SSN or MRN.

How do you encrypt an email in Outlook 2013? +

Outlook 2013 supports S/MIME but not Microsoft Purview Message Encryption. Install an S/MIME certificate in Windows through the personal certificate store. Open Outlook, go to File, Options, Trust Center, Trust Center Settings, Email Security. Under Encrypted email, click Settings, pick your certificate, and choose to sign or encrypt by default. To encrypt a specific message, click the encrypt icon in the compose ribbon before sending. Recipients need S/MIME support in their client and a cached copy of your public key.

How do you use encrypted email in daily workflow? +

Set a policy. Encrypt any message containing PHI, PII, or financial data. Use S/MIME for peer recipients who hold certificates. Use portal encryption or Outlook Encrypt for external recipients on any provider. Verify recipient email address before sending. Confirm identity by phone before releasing any attachment password. Log the send in the practice communication system if required by policy. Train staff on the trigger words that identify sensitive content and the correct encryption path for each recipient type.

Can you encrypt an email to a recipient without setup on their side? +

Yes, with portal-based encryption. Outlook Encrypt, Gmail confidential mode, and third-party gateways all use a portal model where the recipient receives a link, authenticates with a passcode or SSO, and reads the message in a browser. The recipient needs only a modern browser and the passcode. S/MIME and PGP require setup on both sides because the recipient client must decrypt with a private key it holds. Portal delivery is the model to use when the recipient set is variable or non-technical.

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How to Enable Email Encryption in Office 365 for Healthcare Teams

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🔑 Key Takeaways

  • Purview Message Encryption activates on Microsoft 365 E3, E5, Business Premium, or Office 365 E3.
  • The fastest rollout is a mail flow rule that triggers Encrypt-Only on PHI keywords or labels.
  • PowerShell scripts Set-IRMConfiguration and New-TransportRule for reproducible tenant baselines.
  • S/MIME gives cryptographic sender ID but demands certificate distribution to every user device.
  • Pair encryption with MFA, conditional access, DLP, and audit logs for defense-in-depth compliance.

Healthcare teams running Microsoft 365 already own most of the tools they need to send encrypted email. The Encrypt button in Outlook, mail flow rules in Exchange, and rights management services in Azure combine into a working encryption stack that meets HIPAA transmission requirements.

The gap is configuration. Most practices discover that the default Office 365 tenant does not enable email encryption until an administrator turns it on, assigns the right licenses, and writes a mail flow rule. Teams that want a simpler path often pair Microsoft 365 with a dedicated encrypted email service to skip the per-user setup work.

This guide walks through the exact steps to enable email encryption in Office 365 from the admin center, PowerShell, and Outlook. It also covers S/MIME setup, mail flow rules, DLP policies, and the license checks that trip up first-time deployments.

Confirm your Office 365 license includes encryption

License verification comes first. Microsoft Purview Message Encryption ships with Microsoft 365 E3, E5, A3, A5, G3, G5, Business Premium, and Office 365 E3 and E5 plans.

Business Basic and Business Standard do not include Purview by default. Administrators on those plans add Azure Information Protection Premium P1 as an add-on license, upgrade the tenant, or route encryption through a third-party service.

To check coverage, sign in to the Microsoft 365 admin center, open Billing, then Licenses. Confirm that assigned licenses include Azure Rights Management Service and Microsoft Purview Message Encryption entitlements.

Users without the correct license see the Encrypt button greyed out in Outlook. Fixing that means assigning the license, waiting for the tenant to provision, then having the user sign out and back in to refresh the token.

Activate Azure Rights Management in the admin center

Azure Rights Management is the underlying service that Purview Message Encryption depends on. New tenants have it enabled by default, but tenants created before 2018 or tenants that were manually disabled need activation.

Open the Microsoft 365 admin center. Go to Settings, then Org settings, then Services. Find Microsoft Azure Information Protection and select it. Click Manage Microsoft Azure Information Protection settings, then Activate.

The activation runs in the background. After a few minutes, the service shows as Activated and the tenant is ready for message encryption policies.

Administrators who prefer to script this step run Enable-AadrmService or the newer Set-IRMConfiguration cmdlet through Exchange Online PowerShell. Both approaches produce the same result and are documented in Microsoft Purview Message Encryption setup guides at learn.microsoft.com.

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Create a mail flow rule to trigger encryption automatically

Manual encryption depends on staff clicking the Encrypt button on every sensitive message. Mail flow rules remove that dependency by triggering encryption based on message content, sender, recipient, or attached sensitivity labels.

Open the Exchange admin center. Go to Mail flow, then Rules. Click the plus icon and select Apply Office 365 Message Encryption and rights protection to messages.

Set the condition to match the trigger you want. Common conditions include the subject or body containing terms like PHI, patient, or diagnosis, or messages sent to external recipients from clinical users.

Choose the RMS template. Encrypt-Only lets recipients forward, while Do Not Forward blocks reply-all, forwarding, and printing. Save the rule and send a test message to confirm the recipient portal loads as expected.

Enable email encryption in Office 365 with PowerShell

PowerShell is the fastest path for IT teams managing multiple tenants or scripted deployments. Install the Exchange Online Management module, then connect with the appropriate global admin credentials.

Run Install-Module with the name ExchangeOnlineManagement once per machine. Then connect with Connect-ExchangeOnline and the global admin user principal name.

Enable the service with Set-IRMConfiguration and the AutomaticServiceUpdateEnabled parameter set to true. Verify state with Get-IRMConfiguration. The output should show ServiceLocation, LicensingLocation, and InternalLicensingEnabled populated with valid values.

Create mail flow rules with New-TransportRule. Bulk operations save hours when standing up encryption across acquired practices, new subsidiaries, or lab environments where a repeatable baseline matters more than a one-time click-through.

Example

An orthopedic group in Cleveland with 22 users on Microsoft 365 Business Premium needed automatic encryption for outbound referral letters. The IT contractor scripted the rollout through PowerShell, enabling IRM with Set-IRMConfiguration and creating a mail flow rule that triggered on subject keywords like referral, MRI, and X-ray. A second DLP policy caught patterns like ICD-10 codes and insurance member IDs. Total configuration ran 45 minutes. The first test message from a licensed mailbox to a personal Gmail address delivered a Microsoft portal link within seven seconds.

Use the Encrypt button in Outlook desktop and web

Once the tenant is configured, individual senders trigger encryption from Outlook without additional setup. In Outlook desktop, open a new message, click the Options tab, then click Encrypt.

Choose the protection template from the drop-down. Encrypt applies default protection, Do Not Forward blocks reply-all and forwarding, and any custom labels created by the tenant appear alongside the built-in options.

In Outlook on the web, the Encrypt button lives at the top of the new message pane. The behavior is identical to the desktop version, and messages appear in the recipient portal with the same experience.

Mobile users on the Outlook iOS and Android apps get the same Encrypt option under the three-dot menu when composing a message. Recipients open the encrypted message through a portal link and sign in with Microsoft, Google, or a one-time passcode.

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Configure S/MIME for regulated communications

S/MIME provides cryptographic identity verification on top of encryption. It requires certificate distribution to every user and device, which raises the operational cost but delivers sender authentication for compliance-critical exchanges.

Deploy a certificate authority or use a public CA. Push user certificates through Group Policy, Intune, or manual import into the personal certificate store. Confirm the store shows the certificate under Trusted Publishers.

In Outlook 2007 and later, open File, Options, Trust Center, Trust Center Settings, Email Security. Under Encrypted Email, select the S/MIME certificate. Check the boxes to sign outgoing messages and encrypt content and attachments.

S/MIME becomes practical for teams with an existing PKI. Small practices without one usually get better outcomes from Purview Message Encryption or a third-party secure email service that handles keys behind the scenes.

Layer DLP policies on top of encryption rules

Data loss prevention policies inspect messages for regulated content patterns. When a match hits, the policy applies encryption automatically or blocks the message and notifies the sender.

Open the Microsoft Purview compliance portal. Go to Data loss prevention, then Policies. Click Create policy and choose the U.S. Health Insurance Act (HIPAA) template as a starting point.

The template detects patterns like Social Security numbers, ICD-10 codes, DEA numbers, and insurance member IDs. Set the action to apply Purview Message Encryption when the policy matches an outbound message.

Tune the policy over the first two weeks. Review the DLP alert dashboard, adjust match confidence thresholds, and add exceptions for internal training data or test accounts. A tuned policy catches PHI leaks without blocking legitimate clinical email.

💡Pro Tip: Script the tenant baseline with PowerShell for reuse

Save the Set-IRMConfiguration, Enable-OrganizationCustomization, and New-TransportRule commands in a single .ps1 file with comments naming each step. When a mailbox migration, tenant reset, or license upgrade happens, the same script rebuilds the encryption baseline in under 10 minutes. Manual UI clicks are the leading cause of drift between what the risk register says is configured and what the tenant actually has active. A checked-in script also serves as evidence of consistent policy enforcement during an OCR audit.

Test the encryption workflow end to end

Testing catches misconfigured rules before staff sends real PHI through a broken flow. Set up two accounts. Use one licensed Office 365 mailbox as the sender and one external Gmail or Yahoo account as the recipient.

Send a test message with the word PHI in the subject line to trigger the mail flow rule. The external recipient should receive a wrapper message with a link to view the encrypted content.

Open the portal link. Sign in with a Microsoft account, a Google account, or request a one-time passcode. Confirm the message body renders correctly, and reply from the portal to test round-trip encryption.

Document each step with screenshots. Save the DLP report, the mail flow rule configuration, and the PowerShell output. This documentation becomes evidence during HIPAA audits, business associate reviews, and internal security assessments.

Match encryption with the HIPAA Security Rule

The HIPAA Security Rule addresses transmission security under 45 CFR 164.312(e). Encryption is an addressable standard, which means covered entities either implement it or document a reasonable alternative.

Office 365 encryption meets the transmission standard when configured with the mail flow rules and DLP policies described above. Practices should also enable multi-factor authentication, conditional access, and audit logging to satisfy access control and integrity standards.

The HHS Security Rule guidance outlines the full set of technical safeguards. Encryption alone does not satisfy the rule, but it addresses one of the more visible controls that auditors ask about first.

Healthcare organizations also need a signed business associate agreement (BAA) with Microsoft. The BAA is available through the Microsoft Service Trust Portal and covers Office 365, Exchange Online, and Purview Message Encryption when configured for HIPAA workloads. Compliance also depends on healthcare website security features that protect the public-facing side of the practice.

Choose between native encryption and a dedicated service

Native Office 365 encryption works well for organizations that already run on Microsoft 365 E3 or Business Premium and have IT staff to manage mail flow rules, license assignments, and Purview policies.

Small practices without dedicated IT often find the setup and ongoing maintenance costly. Every license change, tenant migration, or Outlook update creates a potential point of failure that a solo IT contractor needs to troubleshoot.

Mailhippo works alongside existing Gmail or Outlook accounts as a HIPAA-compliant secure email service. The base plan includes a business associate agreement and applies TLS with client-side encryption without requiring PGP keys or separate client software. Recipients open messages with one click.

Teams building the workflow further may want to look at enable office 365 email encryption, review outlook 365 enable encryption email options, or benchmark against email encryption office 365 business premium to confirm the plan level covers the needed features.

  • Confirm license coverage before touching mail flow rules.
  • Activate Azure Rights Management once per tenant.
  • Script repeat deployments with PowerShell instead of the admin UI.
  • Layer DLP policies on top of manual encryption for PHI patterns.
  • Document the full configuration for HIPAA audit evidence.

Frequently Asked Questions

Which Office 365 plans include email encryption? +

Microsoft 365 E3, E5, A3, A5, G3, G5, Business Premium, and Office 365 E3 and E5 include Microsoft Purview Message Encryption at no extra cost. Business Basic and Business Standard plans do not include Purview Message Encryption in the base license. Practices on lower-tier plans need to add Azure Information Protection Premium P1, upgrade the tenant, or use a third-party secure email service. Verifying license coverage before enabling encryption avoids failed mail flow rules and confused end users.

How long does it take to enable email encryption in Office 365? +

A single-tenant configuration with existing Purview Message Encryption licensing takes about 30 to 60 minutes. That includes activating Azure Rights Management, creating a mail flow rule, testing an outbound message, and documenting the setup. Multi-tenant rollouts, custom branding, and DLP policy tuning add several hours. Practices adding licenses first should expect provisioning delays of up to 24 hours before the Encrypt button appears in Outlook for newly licensed users.

Do external recipients need an Office 365 account to read encrypted mail? +

No. External recipients receive a notification message with a link to a secure portal hosted by Microsoft. They sign in with a Microsoft account, a Google account, or request a one-time passcode delivered to the recipient email address. The message opens in the browser, and replies stay inside the encrypted thread. Recipients on mobile see the same experience through the Office mobile app or a standard web browser.

Can I enable email encryption in Office 365 with PowerShell? +

Yes. Connect to Exchange Online PowerShell using Connect-ExchangeOnline, then run Set-IRMConfiguration with the AutomaticServiceUpdateEnabled parameter set to true and enable the rights management service with Enable-OrganizationCustomization. Verify the state with Get-IRMConfiguration and Test-IRMConfiguration against a licensed mailbox. PowerShell also handles bulk mail flow rule creation through New-TransportRule, which is faster than the admin center for tenants with dozens of rules or repeated deployment across labs, subsidiaries, and clinics.

How does S/MIME differ from Microsoft Purview Message Encryption? +

S/MIME uses digital certificates issued to individual users. Each sender signs and encrypts the message with keys bound to a verified identity, and each recipient needs a matching certificate to read the message. Microsoft Purview Message Encryption uses a policy-based approach that does not require recipient certificates. S/MIME provides stronger identity assurance for regulated communications with fixed partners. Purview scales better for healthcare teams sending to patients, insurers, and referral partners who do not manage certificates.

Is Office 365 email encryption enough for HIPAA compliance? +

Encryption satisfies the transmission security standard under the HIPAA Security Rule, but compliance requires additional controls. Practices need multi-factor authentication, access controls, audit logs, workforce training, a signed business associate agreement with Microsoft, and documented policies. Encryption without those supporting controls fails an OCR audit even when messages themselves are secured. Treat encryption as one layer inside a broader compliance program rather than the finish line for HIPAA readiness.

What if the Encrypt button does not appear in Outlook after licensing? +

Check three items in order. First, confirm the user license includes Purview Message Encryption in the Microsoft 365 admin center. Second, verify Azure Rights Management is active by running Get-IRMConfiguration and checking that RMSOnlineActivated returns True. Third, sign the user out of Outlook and back in to refresh the license token. If the button still does not appear, restart Outlook in safe mode and clear the Office credentials cache under Windows Credential Manager.