diff --git a/src/course-home/data/api.js b/src/course-home/data/api.js
index 17adeb87..0c1ead2a 100644
--- a/src/course-home/data/api.js
+++ b/src/course-home/data/api.js
@@ -201,6 +201,7 @@ export async function getOutlineTabData(courseId) {
     resumeCourse,
     verifiedMode,
     welcomeMessageHtml,
+    timeOffsetMillis: 0,
   };
 }
 
diff --git a/src/course-home/outline-tab/widgets/UpgradeCard.jsx b/src/course-home/outline-tab/widgets/UpgradeCard.jsx
index fd753fd8..2635e8b3 100644
--- a/src/course-home/outline-tab/widgets/UpgradeCard.jsx
+++ b/src/course-home/outline-tab/widgets/UpgradeCard.jsx
@@ -1,22 +1,223 @@
 import React, { useEffect } from 'react';
 import PropTypes from 'prop-types';
+import { faCheck } from '@fortawesome/free-solid-svg-icons';
+import { FontAwesomeIcon } from '@fortawesome/react-fontawesome';
 
 import { sendTrackEvent, sendTrackingLogEvent } from '@edx/frontend-platform/analytics';
-import { injectIntl, intlShape } from '@edx/frontend-platform/i18n';
-import { Button } from '@edx/paragon';
+import { FormattedDate, FormattedMessage, injectIntl, intlShape } from '@edx/frontend-platform/i18n';
+import { getConfig } from '@edx/frontend-platform';
 
-import messages from '../messages';
 import { useModel } from '../../../generic/model-store';
 import { UpgradeButton } from '../../../generic/upgrade-button';
-import VerifiedCert from '../../../generic/assets/edX_certificate.png';
 
-function UpgradeCard({ courseId, intl, onLearnMore }) {
+function UpsellNoFBECardContent(){
+  return (
+    <ul className="fa-ul">
+      <li>
+      <span className="fa-li"><FontAwesomeIcon icon={faCheck} /></span>
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.verifiedCertLink"
+          defaultMessage="Earn a {verifiedCertLink} of completion to showcase on your resume"
+          values={{
+            verifiedCertLink: (
+              <a className="inline-link-underline" rel="noopener noreferrer" target="_blank" href={`${getConfig().MARKETING_SITE_BASE_URL}/verified-certificate`}>verified certificate</a>
+            ),
+          }}
+        />
+      </li>
+      <li>
+        <span className="fa-li"><FontAwesomeIcon icon={faCheck} /></span> 
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.nonProfitMission"
+          defaultMessage="Support our {nonProfitMission} at edX"
+          values={{
+            nonProfitMission: (
+              <span className="font-weight-bold">non-profit mission</span>
+            ),
+          }}
+        />
+      </li>
+    </ul>
+  );
+}
+
+function UpsellFBEFarAwayCardContent() {
+  return (
+    <ul className="fa-ul">
+      <li>
+        <span className="fa-li"><FontAwesomeIcon icon={faCheck} /></span>
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.verifiedCertLink"
+          defaultMessage="Earn a {verifiedCertLink} of completion to showcase on your resume"
+          values={{
+            verifiedCertLink: (
+              <a className="inline-link-underline" rel="noopener noreferrer" target="_blank" href={`${getConfig().MARKETING_SITE_BASE_URL}/verified-certificate`}>verified certificate</a>
+            ),
+          }}
+        />
+      </li>
+      <li>
+        <span className="fa-li"><FontAwesomeIcon icon={faCheck} /></span> 
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.unlock-graded"
+          defaultMessage="Unlock your access to all course activities, including {gradedAssignments}"
+          values={{
+            gradedAssignments: (
+            <span className="font-weight-bold">graded assignments</span>
+            ),
+          }}
+        />
+      </li>
+      <li>
+        <span className="fa-li"><FontAwesomeIcon icon={faCheck} /></span> 
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.fullAccess"
+          defaultMessage="{fullAccess} to course content and materials, even after the course ends"
+          values={{
+            fullAccess: (
+              <span className="font-weight-bold">Full access</span>
+            ),
+          }}
+        />
+      </li>
+      <li>
+        <span className="fa-li"><FontAwesomeIcon icon={faCheck} /></span> 
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.nonProfitMission"
+          defaultMessage="Support our {nonProfitMission} at edX"
+          values={{
+            nonProfitMission: (
+              <span className="font-weight-bold">non-profit mission</span>
+            ),
+          }}
+        />
+      </li>
+    </ul>
+  );
+}
+
+function UpsellFBESoonCardContent({accessExpirationDate, timezoneFormatArgs}) {
+  return (
+    <div>
+      <p>
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.expirationAccessLoss"
+          defaultMessage="You will lose all access to this course, {includingAnyProgress}, on {date}."
+          values={{
+            includingAnyProgress: (<span className="font-weight-bold">including any progress</span>),
+            date: (<FormattedDate
+                key="accessDate"
+                day="numeric"
+                month="long"
+                value={new Date(accessExpirationDate)}
+                {...timezoneFormatArgs}
+              />),
+          }}
+        />
+      </p>
+      <p>
+        <FormattedMessage
+          id="learning.outline.alert.upgradecard.expirationVerifiedCert"
+          defaultMessage="Upgrading your course enables you to pursue a verified certificate and unlocks numerous features. Learn more about the {benefitsOfUpgrading}."
+          values={{
+            benefitsOfUpgrading: ( <a className="inline-link-underline" rel="noopener noreferrer" target="_blank" href="https://support.edx.org/hc/en-us/articles/360013426573-What-are-the-differences-between-audit-free-and-verified-paid-courses-">benefits of upgrading</a>),
+          }}
+        />
+      </p>
+    </div>
+  );
+}
+
+UpsellFBESoonCardContent.propTypes = {
+  accessExpirationDate: PropTypes.PropTypes.instanceOf(Date).isRequired,
+  timezoneFormatArgs: PropTypes.shape({
+    timeZone: PropTypes.string,
+  })
+};
+
+function ExpirationCountdown({hoursToExpiration}){
+  let expirationText;
+  console.log(hoursToExpiration)
+
+  if(hoursToExpiration >= 24){
+    expirationText =<FormattedMessage
+        id="learning.outline.alert.upgradecard.expiration.days"
+        defaultMessage={`{dayCount, number} {dayCount, plural, 
+          one {day}
+          other {days}} left`}
+        values={{
+          dayCount: (Math.floor(hoursToExpiration/24)),
+        }}
+      />
+  } else if (hoursToExpiration >= 1){
+    expirationText= <FormattedMessage
+    id="learning.outline.alert.upgradecard.expiration.hours"
+    defaultMessage={`{hourCount, number} {hourCount, plural,
+      one {hour}
+      other {hours}} left`}
+    values={{
+      hourCount: (hoursToExpiration),
+    }}
+  />
+  } else {
+    expirationText =<FormattedMessage
+    id="learning.outline.alert.upgradecard.expiration.minutes"
+    defaultMessage="Less than 1 hour left"
+  />
+  }
+  return(<div className="p-3 upsell-warning">{expirationText}</div>)
+}
+
+ExpirationCountdown.propTypes = {
+  hoursToExpiration: PropTypes.number.isRequired,
+};
+
+function AccessExpirationDateBanner({accessExpirationDate, timezoneFormatArgs}){
+  return (
+    <div className="p-3 upsell-warning-light">
+      <FormattedMessage
+        id="learning.outline.alert.upgradecard.expirationr"
+        defaultMessage="Course access will expire {date}"
+        values={{
+          date: (<FormattedDate
+              key="accessExpireDate"
+              day="numeric"
+              month="long"
+              value={accessExpirationDate}
+              {...timezoneFormatArgs}
+            />),
+        }}
+      />
+    </div>
+  );
+}
+
+AccessExpirationDateBanner.propTypes = {
+  accessExpirationDate: PropTypes.PropTypes.instanceOf(Date).isRequired,
+  timezoneFormatArgs: PropTypes.shape({
+    timeZone: PropTypes.string,
+  })
+};
+
+function UpgradeCard({ courseId }) {
   const { org } = useModel('courseHomeMeta', courseId);
   const {
     offer,
     verifiedMode,
+    accessExpiration,
+    datesBannerInfo: {
+      contentTypeGatingEnabled,
+    },
+    datesWidget: {
+      userTimezone,
+    },
+    timeOffsetMillis,
   } = useModel('outline', courseId);
 
+  const timezoneFormatArgs = userTimezone ? { timeZone: userTimezone } : {};
+  const correctedTime = new Date(Date.now() + timeOffsetMillis);
+
+
   if (!verifiedMode) {
     return null;
   }
@@ -55,41 +256,90 @@ function UpgradeCard({ courseId, intl, onLearnMore }) {
     });
   };
 
-  return (
-    <section className="mb-4 p-3 outline-sidebar-upgrade-card">
-      <h2 className="h4" id="outline-sidebar-upgrade-header">{intl.formatMessage(messages.upgradeTitle)}</h2>
-      <div className="row w-100 m-0">
-        <div className="col-6 col-md-12 col-lg-3 col-xl-4 p-0 text-md-center text-lg-left">
-          <img
-            alt={intl.formatMessage(messages.certAlt)}
-            className="w-100"
-            src={VerifiedCert}
-            style={{ maxWidth: '10rem' }}
+  
+  /* 
+  There are 4 parts that change in the upgrade card: 
+    upgradeCardHeaderText
+    expirationBanner
+    upsellMessage
+    offerCode
+  */
+  let upgradeCardHeaderText;
+  let expirationBanner;
+  let upsellMessage;
+  let offerCode;
+
+  if(!!accessExpiration && !!contentTypeGatingEnabled){
+    if(!!offer){ // if there's a first purchase discount, show it
+
+      const hoursToDiscountExpiration = Math.floor((new Date(offer.expirationDate) - correctedTime) /1000/ 60 /60)
+      
+      upgradeCardHeaderText = <FormattedMessage
+          id="learning.outline.alert.upgradecard.firstTimeLearnerDiscount"
+          defaultMessage="{percentage}% First-Time Learner Discount"
+          values={{
+            percentage: (offer.percentage),
+          }}
+        />
+      
+      expirationBanner = <ExpirationCountdown hoursToExpiration={hoursToDiscountExpiration}/>
+      upsellMessage = <UpsellFBEFarAwayCardContent />
+      offerCode = <div className="bg-light p-3 text-center discount-info">
+      <FormattedMessage
+        id="learning.outline.alert.upgradecard.code"
+        defaultMessage="Use code {code} at checkout"
+        values={{
+          code: (<span className="font-weight-bold">{offer.code}</span>),
+        }}
+      />
+    </div>
+
+    } else {
+      const accessExpirationDate = new Date(accessExpiration.expirationDate)
+      const hoursToAccessExpiration = Math.floor((accessExpirationDate - correctedTime) /1000/ 60 /60)
+
+      if(hoursToAccessExpiration >= (7*24)) {
+          upgradeCardHeaderText = <FormattedMessage
+            id="learning.outline.alert.upgradecard.accessExpiration"
+            defaultMessage="Upgrade your course today"
           />
-        </div>
-        <div className="col-6 col-md-12 col-lg-9 col-xl-8 p-0 pl-lg-2 text-center mt-md-2 mt-lg-0">
-          <div className="row w-100 m-0 justify-content-center">
-            <UpgradeButton
-              offer={offer}
-              onClick={logClick}
-              verifiedMode={verifiedMode}
-            />
-            {onLearnMore && (
-              <div className="col-12">
-                <Button
-                  variant="link"
-                  size="sm"
-                  className="pb-0"
-                  onClick={onLearnMore}
-                  aria-labelledby="outline-sidebar-upgrade-header"
-                >
-                  {intl.formatMessage(messages.learnMore)}
-                </Button>
-              </div>
-            )}
-          </div>
-        </div>
+          expirationBanner = <AccessExpirationDateBanner accessExpirationDate={accessExpirationDate} timezoneFormatArgs={timezoneFormatArgs} />
+          upsellMessage = <UpsellFBEFarAwayCardContent />
+        } else { // more urgent messaging if there's less than 7 days left
+          upgradeCardHeaderText = <FormattedMessage
+            id="learning.outline.alert.upgradecard.accessExpirationUrgent"
+            defaultMessage="Course Access Expiration"
+          />
+          expirationBanner = <ExpirationCountdown hoursToExpiration={hoursToAccessExpiration}/>
+          upsellMessage = <UpsellFBESoonCardContent accessExpirationDate={accessExpirationDate} timezoneFormatArgs={timezoneFormatArgs} />
+        }
+      }
+  } else { //FBE is turned off
+    upgradeCardHeaderText = <FormattedMessage
+        id="learning.outline.alert.upgradecard.pursueAverifiedCertificate"
+        defaultMessage="Pursue a verified certificate"
+      />
+    upsellMessage = <UpsellNoFBECardContent />
+  }
+
+
+
+  return (
+    <section className="mb-4 card">
+      <h2 className="h5 m-3" id="outline-sidebar-upgrade-header">
+        {upgradeCardHeaderText}
+      </h2>
+      {expirationBanner}
+      <div className="p-3">
+        {upsellMessage}
       </div>
+      <UpgradeButton
+        offer={offer}
+        onClick={logClick}
+        verifiedMode={verifiedMode}
+        className="ml-3 mr-3 mb-3"
+      />
+      {offerCode}
     </section>
   );
 }
diff --git a/src/course-home/outline-tab/widgets/UpgradeCard.scss b/src/course-home/outline-tab/widgets/UpgradeCard.scss
index 5f369519..2fa28631 100644
--- a/src/course-home/outline-tab/widgets/UpgradeCard.scss
+++ b/src/course-home/outline-tab/widgets/UpgradeCard.scss
@@ -2,3 +2,19 @@
   border: 1px solid $dark-500;
   border-top: 5px solid $dark-500;
 }
+
+.upsell-warning{
+  background-color: #FCF1F4;
+}
+
+.upsell-warning-light{
+  background-color: #FFFAED;;
+}
+
+.discount-info {
+  border-top: 1px solid rgba(0, 0, 0, 0.125);
+}
+
+.inline-link-underline {
+  text-decoration: underline;
+}
\ No newline at end of file