diff --git a/atst/models/task_order.py b/atst/models/task_order.py
index b7c25450..6ea523e2 100644
--- a/atst/models/task_order.py
+++ b/atst/models/task_order.py
@@ -1,4 +1,5 @@
 from enum import Enum
+from datetime import date
 
 import pendulum
 from sqlalchemy import Column, Numeric, String, ForeignKey, Date, Integer
@@ -117,6 +118,11 @@ class TaskOrder(Base, mixins.TimestampsMixin):
     def display_status(self):
         return self.status.value
 
+    @property
+    def days_to_expiration(self):
+        if self.end_date:
+            return (self.end_date - date.today()).days
+
     @property
     def budget(self):
         return sum(
diff --git a/atst/routes/portfolios/task_orders.py b/atst/routes/portfolios/task_orders.py
index d5278ec6..70c30a33 100644
--- a/atst/routes/portfolios/task_orders.py
+++ b/atst/routes/portfolios/task_orders.py
@@ -26,6 +26,7 @@ def portfolio_funding(portfolio_id):
             "start_date",
             "end_date",
             "display_status",
+            "days_to_expiration",
             "balance",
         ]
     }
@@ -45,6 +46,7 @@ def portfolio_funding(portfolio_id):
         if active_task_orders
         else None
     )
+    funded = len(active_task_orders) > 1
     total_balance = sum([task_order["balance"] for task_order in active_task_orders])
 
     return render_template(
@@ -54,6 +56,7 @@ def portfolio_funding(portfolio_id):
         active_task_orders=active_task_orders,
         expired_task_orders=task_orders_by_status.get(TaskOrderStatus.EXPIRED, []),
         funding_end_date=funding_end_date,
+        funded=funded,
         total_balance=total_balance,
     )
 
diff --git a/atst/utils/json.py b/atst/utils/json.py
index a489fcaa..4ce7bd8d 100644
--- a/atst/utils/json.py
+++ b/atst/utils/json.py
@@ -1,4 +1,5 @@
 from flask.json import JSONEncoder
+from datetime import date
 from atst.models.attachment import Attachment
 
 
@@ -6,4 +7,6 @@ class CustomJSONEncoder(JSONEncoder):
     def default(self, obj):
         if isinstance(obj, Attachment):
             return obj.filename
+        if isinstance(obj, date):
+            return obj.strftime("%Y-%m-%d")
         return JSONEncoder.default(self, obj)
diff --git a/js/components/tables/task_order_list.js b/js/components/tables/task_order_list.js
index d9cc3a2f..d7353307 100644
--- a/js/components/tables/task_order_list.js
+++ b/js/components/tables/task_order_list.js
@@ -21,6 +21,7 @@ export default {
   props: {
     data: Array,
     expired: Boolean,
+    funded: Boolean,
   },
 
   components: {
@@ -47,6 +48,7 @@ export default {
         attr: 'start_date',
         sortFunc: numericSort,
         width: '50%',
+        class: 'period-of-performance',
       },
       {
         displayName: 'Initial Value',
@@ -72,6 +74,7 @@ export default {
         isAscending: false,
         columns: indexBy(prop('displayName'), columns),
       },
+      days_to_exp_alert_limit: 30,
     }
   },
 
diff --git a/script/seed_sample.py b/script/seed_sample.py
index d7361663..801056e9 100644
--- a/script/seed_sample.py
+++ b/script/seed_sample.py
@@ -1,6 +1,7 @@
 # Add root application dir to the python path
 import os
 import sys
+from datetime import datetime, timedelta, date
 
 parent_dir = os.path.abspath(os.path.join(os.path.dirname(__file__), ".."))
 sys.path.append(parent_dir)
@@ -94,9 +95,12 @@ def seed_db():
 
         users.append(user)
 
+    amanda = Users.get_by_dod_id("2345678901")
+
+    # create Portfolios for all users that have funding and are not expiring soon
     for user in users:
         portfolio = Portfolios.create(
-            user, name="{}'s portfolio".format(user.first_name)
+            user, name="{}'s portfolio (not expiring)".format(user.first_name)
         )
         for portfolio_role in PORTFOLIO_USERS:
             ws_role = Portfolios.create_member(user, portfolio, portfolio_role)
@@ -161,6 +165,92 @@ def seed_db():
             environment_names=["dev", "staging", "prod"],
         )
 
+    # Create Portfolio for Amanda with TO that is expiring soon and does not have another TO
+    unfunded_portfolio = Portfolios.create(
+        amanda, name="{}'s portfolio (expiring and unfunded)".format(amanda.first_name)
+    )
+
+    [past_date_1, past_date_2, past_date_3, future_date] = sorted(
+        [
+            random_past_date(year_max=3, year_min=2),
+            random_past_date(year_max=2, year_min=1),
+            random_past_date(year_max=1, year_min=1),
+            (date.today() + timedelta(days=20)),
+        ]
+    )
+
+    date_ranges = [
+        (past_date_1, past_date_2),
+        (past_date_2, past_date_3),
+        (past_date_3, future_date),
+    ]
+    for (start_date, end_date) in date_ranges:
+        task_order = TaskOrderFactory.build(
+            start_date=start_date,
+            end_date=end_date,
+            number=random_task_order_number(),
+            portfolio=unfunded_portfolio,
+        )
+        db.session.add(task_order)
+
+    db.session.commit()
+
+    Applications.create(
+        amanda,
+        portfolio=unfunded_portfolio,
+        name="First Application",
+        description="This is our first application.",
+        environment_names=["dev", "staging", "prod"],
+    )
+
+    # Create Portfolio for Amanda with TO that is expiring soon and has another TO
+    funded_portfolio = Portfolios.create(
+        amanda, name="{}'s portfolio (expiring and funded)".format(amanda.first_name)
+    )
+
+    [
+        past_date_1,
+        past_date_2,
+        past_date_3,
+        past_date_4,
+        future_date_1,
+        future_date_2,
+    ] = sorted(
+        [
+            random_past_date(year_max=3, year_min=2),
+            random_past_date(year_max=2, year_min=1),
+            random_past_date(year_max=1, year_min=1),
+            random_past_date(year_max=1, year_min=1),
+            (date.today() + timedelta(days=20)),
+            random_future_date(year_min=0, year_max=1),
+        ]
+    )
+
+    date_ranges = [
+        (past_date_1, past_date_2),
+        (past_date_2, past_date_3),
+        (past_date_3, future_date_1),
+        (past_date_4, future_date_2),
+    ]
+    for (start_date, end_date) in date_ranges:
+        task_order = TaskOrderFactory.build(
+            start_date=start_date,
+            end_date=end_date,
+            number=random_task_order_number(),
+            portfolio=funded_portfolio,
+        )
+        db.session.add(task_order)
+
+    db.session.commit()
+
+    Applications.create(
+        amanda,
+        portfolio=funded_portfolio,
+        name="First Application",
+        description="This is our first application.",
+        environment_names=["dev", "staging", "prod"],
+    )
+
 
 if __name__ == "__main__":
     config = make_config({"DISABLE_CRL_CHECK": True})
diff --git a/styles/components/_portfolio_layout.scss b/styles/components/_portfolio_layout.scss
index 6702d67d..e74481a3 100644
--- a/styles/components/_portfolio_layout.scss
+++ b/styles/components/_portfolio_layout.scss
@@ -50,6 +50,13 @@
         @include icon-color($color-green);
       }
     }
+
+    .unfunded {
+      color: $color-red;
+      .icon {
+        @include icon-color($color-red);
+      }
+    }
   }
 
   .pending-task-order {
@@ -82,10 +89,17 @@
 
   .view-task-order-link {
     margin-left: $gap * 2;
+
+    .icon--tiny {
+      @include icon-size(10);
+      margin-left: 1rem;
+    }
   }
 
   .portfolio-total-balance {
     margin-top: -$gap;
+    margin-bottom: 3rem;
+
     .row {
       flex-direction: row-reverse;
       margin: 2 * $gap 0;
@@ -98,8 +112,60 @@
   }
 
   table {
+    th{
+      .icon {
+        margin-left: 1rem;
+      }
+
+      &.period-of-performance {
+        color: $color-blue;
+
+        .icon {
+          @include icon-color($color-primary)
+        }
+      }
+    }
+
     td.unused-balance {
       color: $color-red;
     }
+
+    .label--expired {
+      background-color: $color-gray-light;
+    }
+
+    .to-performance-period {
+      &.to-expiring-soon {
+
+        .to-expiration-alert {
+          font-weight: $font-bold;
+          font-size: 1.5rem;
+          margin-left: $gap;
+        }
+
+        &.funded .to-expiration-alert {
+          color: $color-blue;
+
+
+          .icon {
+            @include icon-color($color-blue);
+          }
+        }
+
+        &.unfunded {
+          .to-expiration-alert {
+            color: $color-red;
+          }
+
+          .icon {
+            @include icon-color($color-red);
+          }
+
+          .to-end-date {
+            color: $color-red;
+          }
+        }
+      }
+    }
   }
 }
diff --git a/templates/portfolios/task_orders/index.html b/templates/portfolios/task_orders/index.html
index 783c676d..18653ab1 100644
--- a/templates/portfolios/task_orders/index.html
+++ b/templates/portfolios/task_orders/index.html
@@ -8,15 +8,16 @@
 {% macro ViewLink(task_order) %}
   <a href="{{ url_for('portfolios.view_task_order', portfolio_id=portfolio.id, task_order_id=task_order.id) }}" class="icon-link view-task-order-link">
     <span>View</span>
-    {{ Icon("caret_right") }}
+    {{ Icon("caret_right", classes="icon--tiny") }}
   </a>
 {% endmacro %}
 
-{% macro TaskOrderList(task_orders, label='success', expired=False) %}
+{% macro TaskOrderList(task_orders, label='success', expired=False, funded=False) %}
   <task-order-list
     inline-template
     v-bind:data='{{ task_orders | tojson }}'
     v-bind:expired='{{ 'true' if expired else 'false' }}'
+    v-bind:funded='{{'true' if funded else 'false' }}'
     v-cloak
     >
     <div class='responsive-table-wrapper'>
@@ -27,10 +28,10 @@
               !{ col.displayName }
               <template v-if="col.sortFunc">
                 <span class="sorting-direction" v-if="col.displayName === sortInfo.columnName && sortInfo.isAscending">
-                  {{ Icon("caret_down") }}
+                  {{ Icon("caret_down", classes="icon--tiny") }}
                 </span>
                 <span class="sorting-direction" v-if="col.displayName === sortInfo.columnName && !sortInfo.isAscending">
-                  {{ Icon("caret_up") }}
+                  {{ Icon("caret_up", classes="icon--tiny") }}
                 </span>
               </template>
             </th>
@@ -43,16 +44,29 @@
               <span class='label label--{{ label }}'>!{ taskOrder.display_status }</span>
             </td>
             <td class='table-cell--grow'>
-              <span>
-              <local-datetime
-                v-bind:timestamp="taskOrder.start_date"
-                format="M/D/YYYY">
-                </local-datetime>
-                -
-              <local-datetime
-                v-bind:timestamp="taskOrder.end_date"
-                format="M/D/YYYY">
+              <span :class="{ 'to-performance-period': true, 'to-expiring-soon': (taskOrder.days_to_expiration > 0 && taskOrder.days_to_expiration <= days_to_exp_alert_limit), 'funded': funded && taskOrder.display_status === 'Active', 'unfunded': !funded && taskOrder.display_status === 'Active' }">
+                <local-datetime
+                  v-bind:timestamp="taskOrder.start_date"
+                  format="M/D/YYYY">
+                  </local-datetime>
+                  -
+                <local-datetime
+                  v-bind:timestamp="taskOrder.end_date"
+                  format="M/D/YYYY"
+                  class="to-end-date"
+                  >
                 </local-datetime>
+                <span
+                  v-if="taskOrder.days_to_expiration > 0 && taskOrder.days_to_expiration <= days_to_exp_alert_limit && funded"
+                  class="to-expiration-alert">
+                    {{ Icon('ok') }} Period ending in !{ taskOrder.days_to_expiration } days, but new period funded
+                </span>
+                <span
+                  v-if="taskOrder.days_to_expiration > 0 && taskOrder.days_to_expiration <= days_to_exp_alert_limit && !funded"
+                  class="to-expiration-alert">
+                  {{ Icon('alert') }} Period ends in !{ taskOrder.days_to_expiration } days, submit a new task order<br>
+                </span>
+              </span>
             </td>
             <td class="table-cell--align-right">
               <span v-html='formatDollars(taskOrder.budget)'></span>
@@ -63,7 +77,7 @@
             <td>
               <a v-bind:href="taskOrder.url" class="icon-link view-task-order-link">
                 <span>View</span>
-                {{ Icon("caret_right") }}
+                {{ Icon("caret_right", classes="icon--tiny") }}
               </a>
             </td>
           </tr>
@@ -78,15 +92,22 @@
   <div class='panel'>
     <div class='panel__content portfolio-funding__header row'>
       <h3>Portfolio Funding</h3>
-      <div class='portfolio-funding__header--funded-through {{ "funded" if funding_end_date is not none }}'>
-        {% if funding_end_date %}
+      <div class='portfolio-funding__header--funded-through {{ "funded" if funding_end_date is not none and funded else "unfunded"}}'>
+        {% if funding_end_date and funded %}
           {{ Icon('ok') }}
           Funded through
           <local-datetime
-            timestamp="{{ funding_end_date }}"
+            timestamp='{{ funding_end_date }}'
             format="M/D/YYYY">
-            </local-datetime>
-          {% endif %}
+          </local-datetime>
+        {% elif funding_end_date and not funded %}
+          {{ Icon('alert') }}
+          Funded period ends
+          <local-datetime
+            timestamp='{{ funding_end_date }}'
+            format="M/D/YYYY">
+          </local-datetime>
+        {% endif %}
       </div>
       <a href="{{ url_for("task_orders.new", screen=1, portfolio_id=portfolio.id) }}" class="usa-button">Start a New Task Order</a>
     </div>
@@ -125,7 +146,7 @@
   {% endif %}
 
   {% if active_task_orders %}
-    {{ TaskOrderList(active_task_orders, label='success') }}
+    {{ TaskOrderList(active_task_orders, label='success', funded=funded) }}
     <div class='panel portfolio-total-balance'>
       <div class='panel__content row'>
         <span>{{ total_balance | dollars }}</span>
@@ -135,7 +156,7 @@
   {% endif %}
 
   {% if expired_task_orders %}
-    {{ TaskOrderList(expired_task_orders, label='', expired=True) }}
+    {{ TaskOrderList(expired_task_orders, label='expired', expired=True) }}
   {% endif %}
 </div>
 
diff --git a/tests/routes/portfolios/test_task_orders.py b/tests/routes/portfolios/test_task_orders.py
index 0501d9a6..6bb44b5e 100644
--- a/tests/routes/portfolios/test_task_orders.py
+++ b/tests/routes/portfolios/test_task_orders.py
@@ -1,5 +1,6 @@
 from flask import url_for
 import pytest
+from datetime import timedelta, date
 
 from atst.domain.roles import Roles
 from atst.domain.task_orders import TaskOrders
@@ -17,7 +18,7 @@ from tests.utils import captured_templates
 
 
 class TestPortfolioFunding:
-    def test_unfunded_portfolio(self, app, user_session):
+    def test_portfolio_with_no_task_orders(self, app, user_session):
         portfolio = PortfolioFactory.create()
         user_session(portfolio.owner)
 
@@ -67,6 +68,54 @@ class TestPortfolioFunding:
             assert context["funding_end_date"] is end_date
             assert context["total_balance"] == active_to1.budget + active_to2.budget
 
+    def test_expiring_and_funded_portfolio(self, app, user_session):
+        portfolio = PortfolioFactory.create()
+        user_session(portfolio.owner)
+
+        expiring_to = TaskOrderFactory.create(
+            portfolio=portfolio,
+            start_date=random_past_date(),
+            end_date=(date.today() + timedelta(days=10)),
+            number="42",
+        )
+        active_to = TaskOrderFactory.create(
+            portfolio=portfolio,
+            start_date=random_past_date(),
+            end_date=random_future_date(year_min=1, year_max=2),
+            number="43",
+        )
+
+        with captured_templates(app) as templates:
+            response = app.test_client().get(
+                url_for("portfolios.portfolio_funding", portfolio_id=portfolio.id)
+            )
+
+            assert response.status_code == 200
+            _, context = templates[0]
+            assert context["funding_end_date"] is active_to.end_date
+            assert context["funded"] == True
+
+    def test_expiring_and_unfunded_portfolio(self, app, user_session):
+        portfolio = PortfolioFactory.create()
+        user_session(portfolio.owner)
+
+        expiring_to = TaskOrderFactory.create(
+            portfolio=portfolio,
+            start_date=random_past_date(),
+            end_date=(date.today() + timedelta(days=10)),
+            number="42",
+        )
+
+        with captured_templates(app) as templates:
+            response = app.test_client().get(
+                url_for("portfolios.portfolio_funding", portfolio_id=portfolio.id)
+            )
+
+            assert response.status_code == 200
+            _, context = templates[0]
+            assert context["funding_end_date"] is expiring_to.end_date
+            assert context["funded"] == False
+
 
 class TestTaskOrderInvitations:
     def setup(self):