diff --git a/.circleci/config.yml b/.circleci/config.yml
index c28b28a7..c1d2d810 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -96,6 +96,7 @@ commands:
             apk del --purge build
       - run:
           name: Login to Azure CLI
+          shell: /bin/sh -o pipefail
           command: |
             az login \
               --service-principal \
diff --git a/.secrets.baseline b/.secrets.baseline
index 45f10336..d2fd7baf 100644
--- a/.secrets.baseline
+++ b/.secrets.baseline
@@ -3,7 +3,7 @@
     "files": "^.secrets.baseline$|^.*pgsslrootcert.yml$",
     "lines": null
   },
-  "generated_at": "2020-02-12T18:51:01Z",
+  "generated_at": "2020-02-17T20:49:33Z",
   "plugins_used": [
     {
       "base64_limit": 4.5,
@@ -82,7 +82,7 @@
         "hashed_secret": "afc848c316af1a89d49826c5ae9d00ed769415f3",
         "is_secret": false,
         "is_verified": false,
-        "line_number": 44,
+        "line_number": 48,
         "type": "Secret Keyword"
       }
     ],
diff --git a/README.md b/README.md
index accecd38..2982ff33 100644
--- a/README.md
+++ b/README.md
@@ -219,6 +219,10 @@ To generate coverage reports for the Javascript tests:
 
 - `ASSETS_URL`: URL to host which serves static assets (such as a CDN).
 - `AZURE_ACCOUNT_NAME`: The name for the Azure blob storage account
+- `AZURE_CALC_CLIENT_ID`: The client id used to generate a token for the Azure pricing calculator
+- `AZURE_CALC_RESOURCE`: The resource URL used to generate a token for the Azure pricing calculator
+- `AZURE_CALC_SECRET`: The secret key used to generate a token for the Azure pricing calculator
+- `AZURE_CALC_URL`: The redirect URL for the Azure pricing calculator
 - `AZURE_LOGIN_URL`: The URL used to login for an Azure instance.
 - `AZURE_STORAGE_KEY`: A valid secret key for the Azure blob storage account
 - `AZURE_TO_BUCKET_NAME`: The Azure blob storage container name for task order uploads
diff --git a/atst/domain/csp/cloud/azure_cloud_provider.py b/atst/domain/csp/cloud/azure_cloud_provider.py
index 679d5cbd..39c2e83a 100644
--- a/atst/domain/csp/cloud/azure_cloud_provider.py
+++ b/atst/domain/csp/cloud/azure_cloud_provider.py
@@ -1738,7 +1738,6 @@ class AzureCloudProvider(CloudProviderInterface):
         cost_mgmt_url = (
             f"/providers/Microsoft.CostManagement/query?api-version=2019-11-01"
         )
-
         try:
             result = self.sdk.requests.post(
                 f"{self.sdk.cloud.endpoints.resource_manager}{payload.invoice_section_id}{cost_mgmt_url}",
@@ -1770,3 +1769,17 @@ class AzureCloudProvider(CloudProviderInterface):
                 result.status_code,
                 f"azure application error getting reporting data. {str(exc)}",
             )
+
+    def _get_calculator_creds(self):
+        authority = f"{self.sdk.cloud.endpoints.active_directory}/{self.tenant_id}"
+        context = self.sdk.adal.AuthenticationContext(authority=authority)
+        response = context.acquire_token_with_client_credentials(
+            self.config.get("AZURE_CALC_RESOURCE"),
+            self.config.get("AZURE_CALC_CLIENT_ID"),
+            self.config.get("AZURE_CALC_SECRET"),
+        )
+        return response.get("accessToken")
+
+    def get_calculator_url(self):
+        calc_access_token = self._get_calculator_creds()
+        return f"{self.config.get('AZURE_CALC_URL')}?access_token={calc_access_token}"
diff --git a/atst/domain/task_orders.py b/atst/domain/task_orders.py
index 44d6b47e..7a538c2d 100644
--- a/atst/domain/task_orders.py
+++ b/atst/domain/task_orders.py
@@ -90,3 +90,13 @@ class TaskOrders(BaseDomainClass):
             )
             .all()
         )
+
+    @classmethod
+    def get_clins_for_create_billing_instructions(cls):
+        return (
+            db.session.query(CLIN)
+            .filter(
+                CLIN.last_sent_at.is_(None), CLIN.start_date < pendulum.now(tz="UTC")
+            )
+            .all()
+        )
diff --git a/atst/forms/portfolio.py b/atst/forms/portfolio.py
index 7c4e6644..74f5330d 100644
--- a/atst/forms/portfolio.py
+++ b/atst/forms/portfolio.py
@@ -33,6 +33,7 @@ class PortfolioForm(BaseForm):
 class PortfolioCreationForm(PortfolioForm):
     defense_component = SelectMultipleField(
         translate("forms.portfolio.defense_component.title"),
+        description=translate("forms.portfolio.defense_component.help_text"),
         choices=SERVICE_BRANCHES,
         widget=ListWidget(prefix_label=False),
         option_widget=CheckboxInput(),
diff --git a/atst/jobs.py b/atst/jobs.py
index 77a8c2f6..855af5b2 100644
--- a/atst/jobs.py
+++ b/atst/jobs.py
@@ -10,6 +10,7 @@ from atst.domain.csp.cloud import CloudProviderInterface
 from atst.domain.csp.cloud.exceptions import GeneralCSPException
 from atst.domain.csp.cloud.models import (
     ApplicationCSPPayload,
+    BillingInstructionCSPPayload,
     EnvironmentCSPPayload,
     UserCSPPayload,
     UserRoleCSPPayload,
@@ -111,6 +112,18 @@ def do_create_user(csp: CloudProviderInterface, application_role_ids=None):
             db.session.add(app_role)
 
         db.session.commit()
+        username = payload.user_principal_name
+        send_mail(
+            recipients=[user.email],
+            subject=translate("email.app_role_created.subject"),
+            body=translate(
+                "email.app_role_created.body",
+                {"url": app.config.get("AZURE_LOGIN_URL"), "username": username},
+            ),
+        )
+        app.logger.info(
+            f"Application role created notification email sent. User id: {user.id}"
+        )
 
 
 def do_create_environment(csp: CloudProviderInterface, environment_id=None):
@@ -280,7 +293,7 @@ def dispatch_create_atat_admin_user(self):
 
 
 @celery.task(bind=True)
-def dispatch_send_task_order_files(self):
+def send_task_order_files(self):
     task_orders = TaskOrders.get_for_send_task_order_files()
     recipients = [app.config.get("MICROSOFT_TASK_ORDER_EMAIL_ADDRESS")]
 
@@ -301,7 +314,36 @@ def dispatch_send_task_order_files(self):
             app.logger.exception(err)
             continue
 
-        task_order.pdf_last_sent_at = pendulum.now()
+        task_order.pdf_last_sent_at = pendulum.now(tz="UTC")
         db.session.add(task_order)
 
     db.session.commit()
+
+
+@celery.task(bind=True)
+def create_billing_instruction(self):
+    clins = TaskOrders.get_clins_for_create_billing_instructions()
+    for clin in clins:
+        portfolio = clin.task_order.portfolio
+
+        payload = BillingInstructionCSPPayload(
+            tenant_id=portfolio.csp_data.get("tenant_id"),
+            billing_account_name=portfolio.csp_data.get("billing_account_name"),
+            billing_profile_name=portfolio.csp_data.get("billing_profile_name"),
+            initial_clin_amount=clin.obligated_amount,
+            initial_clin_start_date=str(clin.start_date),
+            initial_clin_end_date=str(clin.end_date),
+            initial_clin_type=clin.number,
+            initial_task_order_id=str(clin.task_order_id),
+        )
+
+        try:
+            app.csp.cloud.create_billing_instruction(payload)
+        except (AzureError) as err:
+            app.logger.exception(err)
+            continue
+
+        clin.last_sent_at = pendulum.now(tz="UTC")
+        db.session.add(clin)
+
+    db.session.commit()
diff --git a/atst/models/clin.py b/atst/models/clin.py
index accab107..a96e907f 100644
--- a/atst/models/clin.py
+++ b/atst/models/clin.py
@@ -66,12 +66,14 @@ class CLIN(Base, mixins.TimestampsMixin):
         )
 
     def to_dictionary(self):
-        return {
+        data = {
             c.name: getattr(self, c.name)
             for c in self.__table__.columns
             if c.name not in ["id"]
         }
 
+        return data
+
     @property
     def is_active(self):
         return (
diff --git a/atst/queue.py b/atst/queue.py
index 10bcb350..dcd123d1 100644
--- a/atst/queue.py
+++ b/atst/queue.py
@@ -27,6 +27,14 @@ def update_celery(celery, app):
             "task": "atst.jobs.dispatch_create_environment_role",
             "schedule": 60,
         },
+        "beat-send_task_order_files": {
+            "task": "atst.jobs.send_task_order_files",
+            "schedule": 60,
+        },
+        "beat-create_billing_instruction": {
+            "task": "atst.jobs.create_billing_instruction",
+            "schedule": 60,
+        },
     }
 
     class ContextTask(celery.Task):
diff --git a/atst/routes/portfolios/index.py b/atst/routes/portfolios/index.py
index 6472fca1..02805480 100644
--- a/atst/routes/portfolios/index.py
+++ b/atst/routes/portfolios/index.py
@@ -50,9 +50,7 @@ def reports(portfolio_id):
         "portfolios/reports/index.html",
         portfolio=portfolio,
         # wrapped in str() because this sum returns a Decimal object
-        total_portfolio_value=str(
-            portfolio.total_obligated_funds + portfolio.upcoming_obligated_funds
-        ),
+        total_portfolio_value=str(portfolio.total_obligated_funds),
         current_obligated_funds=current_obligated_funds,
         expired_task_orders=Reports.expired_task_orders(portfolio),
         retrieved=pendulum.now(),  # mocked datetime of reporting data retrival
diff --git a/config/base.ini b/config/base.ini
index 3aa9ad86..a587c74f 100644
--- a/config/base.ini
+++ b/config/base.ini
@@ -3,6 +3,10 @@ ASSETS_URL
 AZURE_AADP_QTY=5
 AZURE_ACCOUNT_NAME
 AZURE_CLIENT_ID
+AZURE_CALC_CLIENT_ID
+AZURE_CALC_RESOURCE="http://azurecom.onmicrosoft.com/acom-prod/"
+AZURE_CALC_SECRET
+AZURE_CALC_URL="https://azure.microsoft.com/en-us/pricing/calculator/"
 AZURE_GRAPH_RESOURCE="https://graph.microsoft.com/"
 AZURE_LOGIN_URL="https://portal.azure.com/"
 AZURE_POLICY_LOCATION=policies
diff --git a/styles/components/_forms.scss b/styles/components/_forms.scss
index f11af8f8..6921eb01 100644
--- a/styles/components/_forms.scss
+++ b/styles/components/_forms.scss
@@ -2,10 +2,6 @@
 .form-row {
   margin: ($gap * 4) 0;
 
-  &--bordered {
-    border-bottom: $color-gray-lighter 1px solid;
-  }
-
   .form-col {
     flex-grow: 1;
 
@@ -22,8 +18,9 @@
     }
 
     .usa-input {
-      input {
-        max-width: none;
+      input,
+      textarea {
+        max-width: $max-input-width;
       }
     }
   }
@@ -204,6 +201,10 @@
   }
 }
 
-.form-container__half {
-  max-width: 46rem;
+.form-container {
+  margin-bottom: $action-footer-height + $large-spacing;
+
+  &--narrow {
+    max-width: $max-input-width;
+  }
 }
diff --git a/styles/components/_member_form.scss b/styles/components/_member_form.scss
index 5cbeaf87..3644fce2 100644
--- a/styles/components/_member_form.scss
+++ b/styles/components/_member_form.scss
@@ -5,17 +5,11 @@
     margin-left: 0;
   }
 
-  .input__inline-fields {
-    text-align: left;
-
-    .usa-input__choices label {
-      font-weight: $font-bold;
-    }
-  }
-
   .input__inline-fields {
     padding: $gap * 2;
     border: 1px solid $color-gray-lighter;
+    text-align: left;
+    max-width: 100%;
 
     &.checked {
       border: 1px solid $color-blue;
@@ -33,7 +27,7 @@
 
   .user-info {
     .usa-input {
-      width: 45rem;
+      max-width: $max-input-width;
 
       input,
       label,
@@ -53,8 +47,7 @@
   }
 }
 
-#modal--add-app-mem,
-#modal--add-portfolio-manager {
+.form-content--member-form {
   .modal__body {
     min-width: 75rem;
   }
diff --git a/styles/components/_portfolio_layout.scss b/styles/components/_portfolio_layout.scss
index e9af6d5e..8aae2ca5 100644
--- a/styles/components/_portfolio_layout.scss
+++ b/styles/components/_portfolio_layout.scss
@@ -519,3 +519,15 @@
     }
   }
 }
+
+#portfolio-create {
+  .usa-input__choices {
+    .usa-input__title {
+      font-weight: $font-bold;
+    }
+
+    label {
+      font-size: $base-font-size;
+    }
+  }
+}
diff --git a/styles/core/_util.scss b/styles/core/_util.scss
index 7fd8e152..0790a121 100644
--- a/styles/core/_util.scss
+++ b/styles/core/_util.scss
@@ -98,7 +98,3 @@ hr {
 .usa-section {
   padding: 0;
 }
-
-.form {
-  margin-bottom: $action-footer-height + $large-spacing;
-}
diff --git a/styles/core/_variables.scss b/styles/core/_variables.scss
index 09b838f3..f98a3663 100644
--- a/styles/core/_variables.scss
+++ b/styles/core/_variables.scss
@@ -21,6 +21,7 @@ $home-pg-icon-width: 6rem;
 $large-spacing: 4rem;
 $max-page-width: $max-panel-width + $sidenav-expanded-width + $large-spacing;
 $action-footer-height: 6rem;
+$max-input-width: 46rem;
 
 /*
  * USWDS Variables
diff --git a/styles/elements/_inputs.scss b/styles/elements/_inputs.scss
index c424b723..6bd3acbb 100644
--- a/styles/elements/_inputs.scss
+++ b/styles/elements/_inputs.scss
@@ -58,7 +58,7 @@
 
 .usa-input {
   margin: ($gap * 2) 0;
-  max-width: 75rem;
+  max-width: $max-input-width;
 
   &-label-helper {
     font-size: $small-font-size;
@@ -111,8 +111,7 @@
     @include h5;
 
     font-weight: normal;
-
-    @include line-max;
+    max-width: $max-input-width;
 
     .icon-link {
       padding: 0 ($gap / 2);
@@ -180,6 +179,10 @@
           left: -3rem;
         }
       }
+
+      .usa-input__title {
+        margin-bottom: $gap;
+      }
     }
 
     select {
@@ -372,19 +375,15 @@ select {
 .phone-input {
   display: flex;
   flex-direction: row;
+  justify-content: flex-start;
 
   &__phone {
     margin-right: $gap * 4;
+    flex-grow: 1;
 
     .usa-input {
       margin: 0;
 
-      input,
-      label,
-      .usa-input__message {
-        max-width: 20rem;
-      }
-
       .icon-validation {
         left: 20rem;
       }
@@ -392,7 +391,8 @@ select {
   }
 
   &__extension {
-    margin-left: $gap * 4;
+    margin-right: $gap * 4;
+    flex-grow: 0;
 
     .usa-input {
       margin: 0;
diff --git a/styles/sections/_task_order.scss b/styles/sections/_task_order.scss
index 79f391e0..1edc5b66 100644
--- a/styles/sections/_task_order.scss
+++ b/styles/sections/_task_order.scss
@@ -140,6 +140,10 @@
   &__confirmation {
     margin-left: $gap * 8;
   }
+
+  .usa-input {
+    max-width: 100%;
+  }
 }
 
 .task-order__modal-cancel {
diff --git a/templates/applications/fragments/members.html b/templates/applications/fragments/members.html
index f60fcba8..5fbecd35 100644
--- a/templates/applications/fragments/members.html
+++ b/templates/applications/fragments/members.html
@@ -36,7 +36,7 @@
       {% set invite_expired = member.role_status == 'invite_expired' %}
       {%- if user_can(permissions.EDIT_APPLICATION_MEMBER) %}
         {% set modal_name = "edit_member-{}".format(loop.index) %}
-        {% call Modal(modal_name, classes="form-content--app-mem") %}
+        {% call Modal(modal_name, classes="form-content--member-form") %}
           <div class="modal__form--header">
             <h1>{{ Icon('avatar') }} {{ "portfolios.applications.members.form.edit_access_header" | translate({ "user": member.user_name }) }}</h1>
           </div>
@@ -56,7 +56,7 @@
 
         {%- if invite_pending or invite_expired %}
           {% set resend_invite_modal = "resend_invite-{}".format(member.role_id) %}
-          {% call Modal(resend_invite_modal, classes="form-content--app-mem") %}
+          {% call Modal(resend_invite_modal, classes="form-content--member-form") %}
             <div class="modal__form--header">
               <h1>{{ "portfolios.applications.members.new.verify" | translate }}</h1>
             </div>
@@ -183,6 +183,7 @@
             modal=new_member_modal_name,
           )
         ],
+        classes="form-content--member-form",
       ) }}
   {% endif %}
   </div>
diff --git a/templates/applications/new/step_1.html b/templates/applications/new/step_1.html
index 39656257..688aa5a3 100644
--- a/templates/applications/new/step_1.html
+++ b/templates/applications/new/step_1.html
@@ -22,7 +22,7 @@
   {% include "fragments/flash.html" %}
 
   <base-form inline-template :enable-save="true">
-    <form method="POST" action="{{ action }}" v-on:submit="handleSubmit" class="form">
+    <form method="POST" action="{{ action }}" v-on:submit="handleSubmit" class="form-container">
       {{ form.csrf_token }}
       <div class="form-row">
         <div class="form-col">
diff --git a/templates/applications/new/step_2.html b/templates/applications/new/step_2.html
index fe07b44d..5fa6be34 100644
--- a/templates/applications/new/step_2.html
+++ b/templates/applications/new/step_2.html
@@ -21,7 +21,7 @@
   </p>
   <hr>
   <application-environments inline-template v-bind:initial-data='{{ form.data|tojson }}'>
-    <form method="POST" action="{{ url_for('applications.update_new_application_step_2', portfolio_id=portfolio.id, application_id=application.id) }}" v-on:submit="handleSubmit" class="form">
+    <form method="POST" action="{{ url_for('applications.update_new_application_step_2', portfolio_id=portfolio.id, application_id=application.id) }}" v-on:submit="handleSubmit" class="form-container">
       <div class="subheading">{{ 'portfolios.applications.environments_heading' | translate }}</div>
       <div class="panel">
         <div class="panel__content">
diff --git a/templates/applications/settings.html b/templates/applications/settings.html
index 1ec7be37..9fc42a17 100644
--- a/templates/applications/settings.html
+++ b/templates/applications/settings.html
@@ -20,7 +20,7 @@
 
   {% if user_can(permissions.EDIT_APPLICATION) %}
     <base-form inline-template>
-      <form method="POST" action="{{ url_for('applications.update', application_id=application.id) }}" class="col col--half">
+      <form method="POST" action="{{ url_for('applications.update', application_id=application.id) }}" class="form-container--narrow">
         {{ application_form.csrf_token }}
         {{ TextInput(application_form.name, validation="applicationName", optional=False) }}
         {{ TextInput(application_form.description, validation="defaultTextAreaField", paragraph=True, optional=True, showOptional=False) }}
diff --git a/templates/components/multi_step_modal_form.html b/templates/components/multi_step_modal_form.html
index a7f71edf..d3c9b520 100644
--- a/templates/components/multi_step_modal_form.html
+++ b/templates/components/multi_step_modal_form.html
@@ -25,10 +25,10 @@
   </div>
 {% endmacro %}
 
-{% macro MultiStepModalForm(name, form, form_action, steps, dismissable=False) -%}
+{% macro MultiStepModalForm(name, form, form_action, steps, dismissable=False, classes="") -%}
   {% set step_count = steps|length %}
   <multi-step-modal-form inline-template :steps={{ step_count }}>
-    {% call Modal(name=name, dismissable=dismissable) %}
+    {% call Modal(name=name, dismissable=dismissable, classes=classes) %}
       <form id="{{ name }}" action="{{ form_action }}" method="POST" v-on:submit="handleSubmit">
         {{ form.csrf_token }}
         <div v-if="$root.activeModal === '{{ name }}'">
diff --git a/templates/portfolios/admin.html b/templates/portfolios/admin.html
index 40721c0d..6e0e795d 100644
--- a/templates/portfolios/admin.html
+++ b/templates/portfolios/admin.html
@@ -13,7 +13,7 @@
   <div v-cloak class="portfolio-admin">
     {% include "fragments/flash.html" %}
     <!-- max width of this section is 460px -->
-    <section class="form-container__half">
+    <section class="form-container--narrow">
       <h3>Portfolio name and component</h3>
       {% if user_can(permissions.EDIT_PORTFOLIO_NAME) %}
         <base-form inline-template>
diff --git a/templates/portfolios/fragments/portfolio_members.html b/templates/portfolios/fragments/portfolio_members.html
index 91e99d24..6e9c4be2 100644
--- a/templates/portfolios/fragments/portfolio_members.html
+++ b/templates/portfolios/fragments/portfolio_members.html
@@ -14,7 +14,7 @@
       {% set invite_expired = member.status == 'invite_expired' %}
 
       {% set modal_name = "edit_member-{}".format(loop.index) %}
-      {% call Modal(modal_name, classes="form-content--app-mem") %}
+      {% call Modal(modal_name, classes="form-content--member-form") %}
         <div class="modal__form--header">
           <h1>{{ Icon('avatar') }} {{ "portfolios.applications.members.form.edit_access_header" | translate({ "user": member.user_name }) }}</h1>
         </div>
@@ -34,7 +34,7 @@
 
       {% if invite_pending or invite_expired -%}
         {% set resend_invite_modal = "resend_invite-{}".format(member.role_id) %}
-        {% call Modal(resend_invite_modal, classes="form-content--app-mem") %}
+        {% call Modal(resend_invite_modal, classes="form-content--member-form") %}
           <div class="modal__form--header">
             <h1>{{ "portfolios.applications.members.new.verify" | translate }}</h1>
           </div>
@@ -182,6 +182,7 @@
           modal=new_manager_modal,
         )
       ],
+      classes="form-content--member-form",
     ) }}
   {% endif %}
 </div>
diff --git a/templates/portfolios/new/step_1.html b/templates/portfolios/new/step_1.html
index d7d4f522..0173d031 100644
--- a/templates/portfolios/new/step_1.html
+++ b/templates/portfolios/new/step_1.html
@@ -19,24 +19,25 @@
   {{ StickyCTA(text="portfolios.new.cta_step_1"|translate, context=("portfolios.new.sticky_header_context"|translate({"step": "1"}) )) }}
   <base-form inline-template>
     <div class="row">
-      <form id="portfolio-create" class="col form" action="{{ url_for('portfolios.create_portfolio') }}" method="POST">
+      <form id="portfolio-create" class="col form-container" action="{{ url_for('portfolios.create_portfolio') }}" method="POST">
         {{ form.csrf_token }}
-        <div class="form-row form-row--bordered">
+        <div class="form-row">
           <div class="form-col">
             {{ TextInput(form.name, validation="portfolioName", optional=False, classes="form-col") }}
             {{"forms.portfolio.name.help_text" | translate | safe }}
           </div>
         </div>
-        <div class="form-row form-row--bordered">
+        <hr>
+        <div class="form-row">
           <div class="form-col">
             {{ TextInput(form.description, validation="defaultTextAreaField", paragraph=True) }}
             {{"forms.portfolio.description.help_text" | translate | safe }}
           </div>
         </div>
+        <hr>
         <div class="form-row">
           <div class="form-col">
             {{ MultiCheckboxInput(form.defense_component, optional=False) }}
-            {{ "forms.portfolio.defense_component.help_text" | translate | safe }}
           </div>
         </div>
         <div
diff --git a/templates/task_orders/builder_base.html b/templates/task_orders/builder_base.html
index 41c253f6..7ee402fb 100644
--- a/templates/task_orders/builder_base.html
+++ b/templates/task_orders/builder_base.html
@@ -28,7 +28,7 @@
 
       {% include "fragments/flash.html" %}
 
-      <div class="task-order form">
+      <div class="task-order form-container">
         {% block to_builder_form_field %}{% endblock %}
       </div>
       <div
diff --git a/tests/domain/cloud/test_azure_csp.py b/tests/domain/cloud/test_azure_csp.py
index b6a71501..5deddc63 100644
--- a/tests/domain/cloud/test_azure_csp.py
+++ b/tests/domain/cloud/test_azure_csp.py
@@ -1523,3 +1523,23 @@ def test_update_tenant_creds(mock_azure: AzureCloudProvider):
         assert updated_secret == KeyVaultCredentials(
             **{**existing_secrets, **MOCK_CREDS}
         )
+
+
+def test_get_calculator_creds(mock_azure: AzureCloudProvider):
+    mock_azure.sdk.adal.AuthenticationContext.return_value.acquire_token_with_client_credentials.return_value = {
+        "accessToken": "TOKEN"
+    }
+    assert mock_azure._get_calculator_creds() == "TOKEN"
+
+
+def test_get_calculator_url(mock_azure: AzureCloudProvider):
+    with patch.object(
+        AzureCloudProvider,
+        "_get_calculator_creds",
+        wraps=mock_azure._get_calculator_creds,
+    ) as _get_calculator_creds:
+        _get_calculator_creds.return_value = "TOKEN"
+        assert (
+            mock_azure.get_calculator_url()
+            == f"{mock_azure.config.get('AZURE_CALC_URL')}?access_token=TOKEN"
+        )
diff --git a/tests/domain/test_task_orders.py b/tests/domain/test_task_orders.py
index 5999677a..4b56b030 100644
--- a/tests/domain/test_task_orders.py
+++ b/tests/domain/test_task_orders.py
@@ -9,6 +9,27 @@ from atst.models.task_order import TaskOrder, SORT_ORDERING, Status
 from tests.factories import TaskOrderFactory, CLINFactory, PortfolioFactory
 
 
+@pytest.fixture
+def new_task_order():
+    return TaskOrderFactory.create(create_clins=[{}])
+
+
+@pytest.fixture
+def updated_task_order():
+    return TaskOrderFactory.create(
+        create_clins=[{"last_sent_at": pendulum.date(2020, 2, 1)}],
+        pdf_last_sent_at=pendulum.date(2020, 1, 1),
+    )
+
+
+@pytest.fixture
+def sent_task_order():
+    return TaskOrderFactory.create(
+        create_clins=[{"last_sent_at": pendulum.date(2020, 1, 1)}],
+        pdf_last_sent_at=pendulum.date(2020, 1, 1),
+    )
+
+
 def test_create_adds_clins():
     portfolio = PortfolioFactory.create()
     clins = [
@@ -181,19 +202,18 @@ def test_allows_alphanumeric_number():
         assert TaskOrders.create(portfolio.id, number, [], None)
 
 
-def test_get_for_send_task_order_files():
-    new_to = TaskOrderFactory.create(create_clins=[{}])
-    updated_to = TaskOrderFactory.create(
-        create_clins=[{"last_sent_at": pendulum.datetime(2020, 2, 1)}],
-        pdf_last_sent_at=pendulum.datetime(2020, 1, 1),
-    )
-    sent_to = TaskOrderFactory.create(
-        create_clins=[{"last_sent_at": pendulum.datetime(2020, 1, 1)}],
-        pdf_last_sent_at=pendulum.datetime(2020, 1, 1),
-    )
-
+def test_get_for_send_task_order_files(
+    new_task_order, updated_task_order, sent_task_order
+):
     updated_and_new_task_orders = TaskOrders.get_for_send_task_order_files()
     assert len(updated_and_new_task_orders) == 2
-    assert sent_to not in updated_and_new_task_orders
-    assert updated_to in updated_and_new_task_orders
-    assert new_to in updated_and_new_task_orders
+    assert sent_task_order not in updated_and_new_task_orders
+    assert updated_task_order in updated_and_new_task_orders
+    assert new_task_order in updated_and_new_task_orders
+
+
+def test_get_clins_for_create_billing_instructions(new_task_order, sent_task_order):
+    new_clins = TaskOrders.get_clins_for_create_billing_instructions()
+    assert len(new_clins) == 1
+    assert new_task_order.clins[0] in new_clins
+    assert sent_task_order.clins[0] not in new_clins
diff --git a/tests/mock_azure.py b/tests/mock_azure.py
index 2ca2a547..e89f6094 100644
--- a/tests/mock_azure.py
+++ b/tests/mock_azure.py
@@ -4,6 +4,9 @@ from unittest.mock import Mock
 from atst.domain.csp.cloud import AzureCloudProvider
 
 AZURE_CONFIG = {
+    "AZURE_CALC_CLIENT_ID": "MOCK",
+    "AZURE_CALC_SECRET": "MOCK",  # pragma: allowlist secret
+    "AZURE_CALC_RESOURCE": "http://calc",
     "AZURE_CLIENT_ID": "MOCK",
     "AZURE_SECRET_KEY": "MOCK",
     "AZURE_TENANT_ID": "MOCK",
diff --git a/tests/test_jobs.py b/tests/test_jobs.py
index 9df83264..eba01f9b 100644
--- a/tests/test_jobs.py
+++ b/tests/test_jobs.py
@@ -6,7 +6,8 @@ from smtplib import SMTPException
 from azure.core.exceptions import AzureError
 
 from atst.domain.csp.cloud import MockCloudProvider
-from atst.domain.csp.cloud.models import UserRoleCSPResult
+from atst.domain.csp.cloud.models import BillingInstructionCSPPayload, UserRoleCSPResult
+from atst.domain.portfolios import Portfolios
 from atst.models import ApplicationRoleStatus, Portfolio, FSMStates
 
 from atst.jobs import (
@@ -16,7 +17,7 @@ from atst.jobs import (
     dispatch_create_user,
     dispatch_create_environment_role,
     dispatch_provision_portfolio,
-    dispatch_send_task_order_files,
+    create_billing_instruction,
     create_environment,
     do_create_user,
     do_provision_portfolio,
@@ -24,10 +25,12 @@ from atst.jobs import (
     do_create_environment_role,
     do_create_application,
     send_PPOC_email,
+    send_task_order_files,
 )
 from tests.factories import (
     ApplicationFactory,
     ApplicationRoleFactory,
+    CLINFactory,
     EnvironmentFactory,
     EnvironmentRoleFactory,
     PortfolioFactory,
@@ -135,28 +138,63 @@ def test_create_application_job_is_idempotent(csp):
     csp.create_application.assert_not_called()
 
 
-def test_create_user_job(session, csp, app):
-    portfolio = PortfolioFactory.create(
-        csp_data={
-            "tenant_id": str(uuid4()),
-            "domain_name": f"rebelalliance.{app.config.get('OFFICE_365_DOMAIN')}",
-        }
-    )
-    application = ApplicationFactory.create(portfolio=portfolio, cloud_id="321")
-    user = UserFactory.create(
-        first_name="Han", last_name="Solo", email="han@example.com"
-    )
-    app_role = ApplicationRoleFactory.create(
-        application=application,
-        user=user,
-        status=ApplicationRoleStatus.ACTIVE,
-        cloud_id=None,
-    )
+class TestCreateUserJob:
+    @pytest.fixture
+    def portfolio(self, app):
+        return PortfolioFactory.create(
+            csp_data={
+                "tenant_id": str(uuid4()),
+                "domain_name": f"rebelalliance.{app.config.get('OFFICE_365_DOMAIN')}",
+            }
+        )
 
-    do_create_user(csp, [app_role.id])
-    session.refresh(app_role)
+    @pytest.fixture
+    def app_1(self, portfolio):
+        return ApplicationFactory.create(portfolio=portfolio, cloud_id="321")
 
-    assert app_role.cloud_id
+    @pytest.fixture
+    def app_2(self, portfolio):
+        return ApplicationFactory.create(portfolio=portfolio, cloud_id="123")
+
+    @pytest.fixture
+    def user(self):
+        return UserFactory.create(
+            first_name="Han", last_name="Solo", email="han@example.com"
+        )
+
+    @pytest.fixture
+    def app_role_1(self, app_1, user):
+        return ApplicationRoleFactory.create(
+            application=app_1,
+            user=user,
+            status=ApplicationRoleStatus.ACTIVE,
+            cloud_id=None,
+        )
+
+    @pytest.fixture
+    def app_role_2(self, app_2, user):
+        return ApplicationRoleFactory.create(
+            application=app_2,
+            user=user,
+            status=ApplicationRoleStatus.ACTIVE,
+            cloud_id=None,
+        )
+
+    def test_create_user_job(self, session, csp, app_role_1):
+        assert not app_role_1.cloud_id
+
+        session.begin_nested()
+        do_create_user(csp, [app_role_1.id])
+        session.rollback()
+
+        assert app_role_1.cloud_id
+
+    def test_create_user_sends_email(self, monkeypatch, csp, app_role_1, app_role_2):
+        mock = Mock()
+        monkeypatch.setattr("atst.jobs.send_mail", mock)
+
+        do_create_user(csp, [app_role_1.id, app_role_2.id])
+        assert mock.call_count == 1
 
 
 def test_dispatch_create_environment(session, monkeypatch):
@@ -380,82 +418,152 @@ def test_create_environment_role():
     assert env_role.cloud_id == "a-cloud-id"
 
 
-# TODO: Refactor the tests related to dispatch_send_task_order_files() into a class
-# and separate the success test into two tests
-def test_dispatch_send_task_order_files(monkeypatch, app):
-    mock = Mock()
-    monkeypatch.setattr("atst.jobs.send_mail", mock)
+class TestSendTaskOrderFiles:
+    @pytest.fixture(scope="function")
+    def send_mail(self, monkeypatch):
+        mock = Mock()
+        monkeypatch.setattr("atst.jobs.send_mail", mock)
+        return mock
 
-    def _download_task_order(MockFileService, object_name):
-        return {"name": object_name}
+    @pytest.fixture(scope="function")
+    def download_task_order(self, monkeypatch):
+        def _download_task_order(MockFileService, object_name):
+            return {"name": object_name}
 
-    monkeypatch.setattr(
-        "atst.domain.csp.files.MockFileService.download_task_order",
-        _download_task_order,
-    )
+        monkeypatch.setattr(
+            "atst.domain.csp.files.MockFileService.download_task_order",
+            _download_task_order,
+        )
 
-    # Create 3 new Task Orders
-    for i in range(3):
-        TaskOrderFactory.create(create_clins=[{"number": "0001"}])
+    def test_sends_multiple_emails(self, send_mail, download_task_order):
+        # Create 3 Task Orders
+        for i in range(3):
+            TaskOrderFactory.create(create_clins=[{"number": "0001"}])
 
-    dispatch_send_task_order_files.run()
+        send_task_order_files.run()
 
-    # Check that send_with_attachment was called once for each task order
-    assert mock.call_count == 3
-    mock.reset_mock()
+        # Check that send_with_attachment was called once for each task order
+        assert send_mail.call_count == 3
 
-    # Create new TO
-    task_order = TaskOrderFactory.create(create_clins=[{"number": "0001"}])
-    assert not task_order.pdf_last_sent_at
+    def test_kwargs(self, send_mail, download_task_order, app):
+        task_order = TaskOrderFactory.create(create_clins=[{"number": "0001"}])
+        send_task_order_files.run()
 
-    dispatch_send_task_order_files.run()
+        # Check that send_with_attachment was called with correct kwargs
+        send_mail.assert_called_once_with(
+            recipients=[app.config.get("MICROSOFT_TASK_ORDER_EMAIL_ADDRESS")],
+            subject=translate(
+                "email.task_order_sent.subject", {"to_number": task_order.number}
+            ),
+            body=translate(
+                "email.task_order_sent.body", {"to_number": task_order.number}
+            ),
+            attachments=[
+                {
+                    "name": task_order.pdf.object_name,
+                    "maintype": "application",
+                    "subtype": "pdf",
+                }
+            ],
+        )
+        assert task_order.pdf_last_sent_at
 
-    # Check that send_with_attachment was called with correct kwargs
-    mock.assert_called_once_with(
-        recipients=[app.config.get("MICROSOFT_TASK_ORDER_EMAIL_ADDRESS")],
-        subject=translate(
-            "email.task_order_sent.subject", {"to_number": task_order.number}
-        ),
-        body=translate("email.task_order_sent.body", {"to_number": task_order.number}),
-        attachments=[
-            {
-                "name": task_order.pdf.object_name,
-                "maintype": "application",
-                "subtype": "pdf",
-            }
-        ],
-    )
+    def test_send_failure(self, monkeypatch):
+        def _raise_smtp_exception(**kwargs):
+            raise SMTPException
 
-    assert task_order.pdf_last_sent_at
+        monkeypatch.setattr("atst.jobs.send_mail", _raise_smtp_exception)
+        task_order = TaskOrderFactory.create(create_clins=[{"number": "0001"}])
+        send_task_order_files.run()
+
+        # Check that pdf_last_sent_at has not been updated
+        assert not task_order.pdf_last_sent_at
+
+    def test_download_failure(self, send_mail, monkeypatch):
+        def _download_task_order(MockFileService, object_name):
+            raise AzureError("something went wrong")
+
+        monkeypatch.setattr(
+            "atst.domain.csp.files.MockFileService.download_task_order",
+            _download_task_order,
+        )
+        task_order = TaskOrderFactory.create(create_clins=[{"number": "0002"}])
+        send_task_order_files.run()
+
+        # Check that pdf_last_sent_at has not been updated
+        assert not task_order.pdf_last_sent_at
 
 
-def test_dispatch_send_task_order_files_send_failure(monkeypatch):
-    def _raise_smtp_exception(**kwargs):
-        raise SMTPException
+class TestCreateBillingInstructions:
+    @pytest.fixture
+    def unsent_clin(self):
+        start_date = pendulum.now().subtract(days=1)
+        portfolio = PortfolioFactory.create(
+            csp_data={
+                "tenant_id": str(uuid4()),
+                "billing_account_name": "fake",
+                "billing_profile_name": "fake",
+            },
+            task_orders=[{"create_clins": [{"start_date": start_date}]}],
+        )
+        return portfolio.task_orders[0].clins[0]
 
-    monkeypatch.setattr("atst.jobs.send_mail", _raise_smtp_exception)
+    def test_update_clin_last_sent_at(self, session, unsent_clin):
+        assert not unsent_clin.last_sent_at
 
-    task_order = TaskOrderFactory.create(create_clins=[{"number": "0001"}])
-    dispatch_send_task_order_files.run()
+        # The session needs to be nested to prevent detached SQLAlchemy instance
+        session.begin_nested()
+        create_billing_instruction()
 
-    # Check that pdf_last_sent_at has not been updated
-    assert not task_order.pdf_last_sent_at
+        # check that last_sent_at has been updated
+        assert unsent_clin.last_sent_at
+        session.rollback()
 
+    def test_failure(self, monkeypatch, session, unsent_clin):
+        def _create_billing_instruction(MockCloudProvider, object_name):
+            raise AzureError("something went wrong")
 
-def test_dispatch_send_task_order_files_download_failure(monkeypatch):
-    mock = Mock()
-    monkeypatch.setattr("atst.jobs.send_mail", mock)
+        monkeypatch.setattr(
+            "atst.domain.csp.cloud.MockCloudProvider.create_billing_instruction",
+            _create_billing_instruction,
+        )
 
-    def _download_task_order(MockFileService, object_name):
-        raise AzureError("something went wrong")
+        # The session needs to be nested to prevent detached SQLAlchemy instance
+        session.begin_nested()
+        create_billing_instruction()
 
-    monkeypatch.setattr(
-        "atst.domain.csp.files.MockFileService.download_task_order",
-        _download_task_order,
-    )
+        # check that last_sent_at has not been updated
+        assert not unsent_clin.last_sent_at
+        session.rollback()
 
-    task_order = TaskOrderFactory.create(create_clins=[{"number": "0002"}])
-    dispatch_send_task_order_files.run()
+    def test_task_order_with_multiple_clins(self, session):
+        start_date = pendulum.now(tz="UTC").subtract(days=1)
+        portfolio = PortfolioFactory.create(
+            csp_data={
+                "tenant_id": str(uuid4()),
+                "billing_account_name": "fake",
+                "billing_profile_name": "fake",
+            },
+            task_orders=[
+                {
+                    "create_clins": [
+                        {"start_date": start_date, "last_sent_at": start_date}
+                    ]
+                }
+            ],
+        )
+        task_order = portfolio.task_orders[0]
+        sent_clin = task_order.clins[0]
 
-    # Check that pdf_last_sent_at has not been updated
-    assert not task_order.pdf_last_sent_at
+        # Add new CLIN to the Task Order
+        new_clin = CLINFactory.create(task_order=task_order)
+        assert not new_clin.last_sent_at
+
+        session.begin_nested()
+        create_billing_instruction()
+        session.add(sent_clin)
+
+        # check that last_sent_at has been update for the new clin only
+        assert new_clin.last_sent_at
+        assert sent_clin.last_sent_at != new_clin.last_sent_at
+        session.rollback()
diff --git a/translations.yaml b/translations.yaml
index 4bb463cc..bc4e1479 100644
--- a/translations.yaml
+++ b/translations.yaml
@@ -83,7 +83,10 @@ errors:
   not_found_sub: This page does not exist.
 email:
   application_invite: "{inviter_name} has invited you to a JEDI cloud application"
-  portfolio_invite: "{inviter_name} has invited you to a JEDI cloud portfolio"
+  app_role_created:
+    subject: Application Role Created
+    body: "Your application role has been created.\nVisit {url}, and use your username, {username}, to log in."
+  portfolio_invite: "{inviter_name} has invited you to a JEDI cloud portfolio."
   portfolio_ready:
     subject: Portfolio Provisioned
     body: "Your portfolio has been provisioned.\nVisit {password_reset_address}, and use your username, {username}, to create a password."
@@ -268,7 +271,7 @@ forms:
       label: Portfolio Name
       length_validation_message: Portfolio names can be between 4-100 characters
       help_text: |
-        <div>
+        <div class="usa-input__help">
           <p>
             Naming can be difficult. Choose a name that is descriptive enough for users to identify the Portfolio. You may consider naming based on your organization.
           </p>
@@ -282,7 +285,7 @@ forms:
     description:
       label: Portfolio Description
       help_text: |
-        <div>
+        <div class="usa-input__help">
           <p>
             Add a brief one to two sentence description of your Portfolio. Consider this your statement of work.
           </p>
@@ -307,11 +310,9 @@ forms:
       title: Select DoD component(s) funding your Portfolio
       validation_message: You must select at least one defense component.
       help_text: |
-        <p>
           Select the DOD component(s) that will fund all Applications within this Portfolio.
           In JEDI, multiple DoD organizations can fund the same Portfolio.<br/>
-          Select all that apply.<br/>
-        </p>
+          Select all that apply.
   attachment:
     object_name:
       length_error: Object name may be no longer than 40 characters.
@@ -515,7 +516,7 @@ portfolios:
     estimate_warning: Reports displayed in JEDI are estimates and not a system of record. To manage your costs, go to Azure by selecting the Login to Azure button above.
     total_value:
       header: Total Portfolio Value
-      tooltip: Total portfolio value is all obligated funds for current and upcoming task orders in this portfolio.
+      tooltip: Total portfolio value is all obligated funds for active task orders in this portfolio.
 task_orders:
   add_new_button: Add New Task Order
   review: