diff --git a/cmd/server/pactasrv/conv/oapi_to_pacta.go b/cmd/server/pactasrv/conv/oapi_to_pacta.go
index ae6b1b5..193be02 100644
--- a/cmd/server/pactasrv/conv/oapi_to_pacta.go
+++ b/cmd/server/pactasrv/conv/oapi_to_pacta.go
@@ -103,12 +103,12 @@ func AnalysisTypeFromOAPI(at api.AnalysisType) (pacta.AnalysisType, error) {
 	return "", oapierr.BadRequest("analysisTypeFromOAPI: unknown analysis type", zap.String("analysis_type", string(at)))
 }
 
-func HoldingsDateFromOAPI(hd *api.HoldingsDate) (*pacta.HoldingsDate, error) {
-	if hd == nil {
+func HoldingsDateFromOAPI(hd api.HoldingsDate) (*pacta.HoldingsDate, error) {
+	if hd.Time == nil {
 		return nil, nil
 	}
 	return &pacta.HoldingsDate{
-		Time: hd.Time,
+		Time: *hd.Time,
 	}, nil
 }
 
diff --git a/cmd/server/pactasrv/conv/pacta_to_oapi.go b/cmd/server/pactasrv/conv/pacta_to_oapi.go
index 5c1f32a..7a93c88 100644
--- a/cmd/server/pactasrv/conv/pacta_to_oapi.go
+++ b/cmd/server/pactasrv/conv/pacta_to_oapi.go
@@ -177,12 +177,12 @@ func InitiativeUserRelationshipToOAPI(i *pacta.InitiativeUserRelationship) (*api
 	}, nil
 }
 
-func HoldingsDateToOAPI(hd *pacta.HoldingsDate) (*api.HoldingsDate, error) {
+func HoldingsDateToOAPI(hd *pacta.HoldingsDate) (api.HoldingsDate, error) {
 	if hd == nil {
-		return nil, nil
+		return api.HoldingsDate{}, nil
 	}
-	return &api.HoldingsDate{
-		Time: hd.Time,
+	return api.HoldingsDate{
+		Time: &hd.Time,
 	}, nil
 }
 
@@ -208,12 +208,9 @@ func IncompleteUploadToOAPI(iu *pacta.IncompleteUpload) (*api.IncompleteUpload,
 	if err != nil {
 		return nil, oapierr.Internal("incompleteUploadToOAPI: failureCodeToOAPI failed", zap.Error(err))
 	}
-	var hd *api.HoldingsDate
-	if iu.Properties.HoldingsDate != nil {
-		hd, err = HoldingsDateToOAPI(iu.Properties.HoldingsDate)
-		if err != nil {
-			return nil, oapierr.Internal("incompleteUploadToOAPI: holdingsDateToOAPI failed", zap.Error(err))
-		}
+	hd, err := HoldingsDateToOAPI(iu.Properties.HoldingsDate)
+	if err != nil {
+		return nil, oapierr.Internal("incompleteUploadToOAPI: holdingsDateToOAPI failed", zap.Error(err))
 	}
 	return &api.IncompleteUpload{
 		Id:                         string(iu.ID),
@@ -255,12 +252,9 @@ func PortfolioToOAPI(p *pacta.Portfolio) (*api.Portfolio, error) {
 	if err != nil {
 		return nil, oapierr.Internal("initiativeToOAPI: portfolioInitiativeMembershipToOAPIInitiative failed", zap.Error(err))
 	}
-	var hd *api.HoldingsDate
-	if p.Properties.HoldingsDate != nil {
-		hd, err = HoldingsDateToOAPI(p.Properties.HoldingsDate)
-		if err != nil {
-			return nil, oapierr.Internal("portfolioToOAPI: holdingsDateToOAPI failed", zap.Error(err))
-		}
+	hd, err := HoldingsDateToOAPI(p.Properties.HoldingsDate)
+	if err != nil {
+		return nil, oapierr.Internal("portfolioToOAPI: holdingsDateToOAPI failed", zap.Error(err))
 	}
 	return &api.Portfolio{
 		Id:                         string(p.ID),
diff --git a/cmd/server/pactasrv/portfolio.go b/cmd/server/pactasrv/portfolio.go
index 41adde6..594acbd 100644
--- a/cmd/server/pactasrv/portfolio.go
+++ b/cmd/server/pactasrv/portfolio.go
@@ -91,7 +91,7 @@ func (s *Server) UpdatePortfolio(ctx context.Context, request api.UpdatePortfoli
 		mutations = append(mutations, db.SetPortfolioDescription(*request.Body.Description))
 	}
 	if request.Body.PropertyHoldingsDate != nil {
-		hd, err := conv.HoldingsDateFromOAPI(request.Body.PropertyHoldingsDate)
+		hd, err := conv.HoldingsDateFromOAPI(*request.Body.PropertyHoldingsDate)
 		if err != nil {
 			return nil, err
 		}
diff --git a/cmd/server/pactasrv/upload.go b/cmd/server/pactasrv/upload.go
index 2f4a59a..08ee393 100644
--- a/cmd/server/pactasrv/upload.go
+++ b/cmd/server/pactasrv/upload.go
@@ -26,11 +26,9 @@ func (s *Server) StartPortfolioUpload(ctx context.Context, request api.StartPort
 	}
 	owner := &pacta.Owner{ID: actorInfo.OwnerID}
 	properties := pacta.PortfolioProperties{}
-	if request.Body.PropertyHoldingsDate != nil {
-		properties.HoldingsDate, err = conv.HoldingsDateFromOAPI(request.Body.PropertyHoldingsDate)
-		if err != nil {
-			return nil, err
-		}
+	properties.HoldingsDate, err = conv.HoldingsDateFromOAPI(request.Body.PropertyHoldingsDate)
+	if err != nil {
+		return nil, err
 	}
 	properties.ESG = conv.OptionalBoolFromOAPI(request.Body.PropertyESG)
 	properties.External = conv.OptionalBoolFromOAPI(request.Body.PropertyExternal)
diff --git a/frontend/components/analysis/ContextualListView.vue b/frontend/components/analysis/ContextualListView.vue
index 37351c0..755c3e4 100644
--- a/frontend/components/analysis/ContextualListView.vue
+++ b/frontend/components/analysis/ContextualListView.vue
@@ -127,6 +127,7 @@ const reportButtonClasses = computed(() => {
         :portfolio-id="props.portfolioId"
         :portfolio-group-id="props.portfolioGroupId"
         :initiative-id="props.initiativeId"
+        :warn-for-duplicate="hasAnyAudits"
         class="p-button-sm"
         @started="() => emit('refresh')"
       />
@@ -137,6 +138,7 @@ const reportButtonClasses = computed(() => {
         :portfolio-id="props.portfolioId"
         :portfolio-group-id="props.portfolioGroupId"
         :initiative-id="props.initiativeId"
+        :warn-for-duplicate="hasAnyReports"
         class="p-button-sm"
         @started="() => emit('refresh')"
       />
diff --git a/frontend/components/analysis/RunButton.vue b/frontend/components/analysis/RunButton.vue
index 384fb9b..fefd659 100644
--- a/frontend/components/analysis/RunButton.vue
+++ b/frontend/components/analysis/RunButton.vue
@@ -1,6 +1,8 @@
 <script setup lang="ts">
 import { type RunAnalysisReq, type Analysis, type AnalysisType } from '@/openapi/generated/pacta'
+import { useConfirm } from 'primevue/useconfirm'
 
+const { require: confirm } = useConfirm()
 const pactaClient = usePACTA()
 const { loading: { withLoading } } = useModal()
 const localePath = useLocalePath()
@@ -14,6 +16,7 @@ const tt = (key: string) => t(`${prefix}.${key}`)
 interface Props {
   analysisType: AnalysisType
   name: string
+  warnForDuplicate?: boolean
   portfolioGroupId?: string
   portfolioId?: string
   initiativeId?: string
@@ -54,15 +57,36 @@ const request = computed<RunAnalysisReq>(() => {
     throw new Error('No portfolio, portfolio group or initiative ID provided')
   }
 })
-const runAnalysis = () => {
+
+const startRun = () => {
   emit('started')
-  return withLoading(
+  clicked.value = true
+  void withLoading(
     () => pactaClient.runAnalysis(request.value)
       .then((resp) => { analysisId.value = resp.analysisId })
       .then(() => { void refreshAnalysisState() }),
     `${prefix}.runAnalysis`,
   )
 }
+const runAnalysis = () => {
+  if (!props.warnForDuplicate) {
+    startRun()
+    return
+  }
+  confirm({
+    header: tt('ConfirmationHeader'),
+    message: tt('ConfirmationMessage'),
+    icon: 'pi pi-copy',
+    position: 'center',
+    blockScroll: true,
+    reject: () => { clicked.value = false },
+    rejectLabel: tt('Cancel Run'),
+    rejectIcon: 'pi pi-times',
+    acceptLabel: tt('Run Anyway'),
+    accept: startRun,
+    acceptIcon: 'pi pi-check',
+  })
+}
 const refreshAnalysisState = async () => {
   const aid = analysisId.value
   if (!aid) {
diff --git a/frontend/components/inputs/HoldingsDate.vue b/frontend/components/inputs/HoldingsDate.vue
index f212d13..8562159 100644
--- a/frontend/components/inputs/HoldingsDate.vue
+++ b/frontend/components/inputs/HoldingsDate.vue
@@ -13,8 +13,8 @@ interface Emits {
 const emit = defineEmits<Emits>()
 
 const model = computed<Date | undefined>({
-  get: () => props.value ? new Date(props.value.time) : undefined,
-  set: (value: Date | undefined) => { emit('update:value', value ? ({ time: value.toISOString() }) : undefined) },
+  get: () => props.value?.time ? new Date(props.value.time) : undefined,
+  set: (value: Date | undefined) => { emit('update:value', value ? ({ time: value.toISOString() }) : ({ time: undefined })) },
 })
 </script>
 
diff --git a/frontend/components/modal/Group.vue b/frontend/components/modal/Group.vue
index ebee878..d1e1f94 100644
--- a/frontend/components/modal/Group.vue
+++ b/frontend/components/modal/Group.vue
@@ -9,5 +9,9 @@
     <!-- TODO(grady) Remove This in Production Environments -->
     <ModalMissingTranslations />
     <PVToast />
+    <PVConfirmDialog
+      class="w-30rem"
+      style="max-width: calc(100vw - 1rem);"
+    />
   </div>
 </template>
diff --git a/frontend/lang/en.json b/frontend/lang/en.json
index 477d065..f6c2586 100644
--- a/frontend/lang/en.json
+++ b/frontend/lang/en.json
@@ -220,7 +220,11 @@
   "components/analysis/RunButton": {
     "Run": "Run",
     "AnalysisTypeAUDIT": "Audit",
-    "AnalysisTypeREPORT": "Report"
+    "AnalysisTypeREPORT": "Report",
+    "ConfirmationHeader": "Run Duplicate Analysis?",
+    "ConfirmationMessage": "It looks like there is already a run for this analysis - if you have changed the settings or underlying data for this analysis, a new run may be warranted, but otherwise this will just return the same analysis as above.",
+    "Run Anyway": "Run Anyway",
+    "Cancel Run": "Nevermind"
   },
   "components/portfolio/group/ListView": {
     "Created At": "Created At",
diff --git a/frontend/openapi/generated/pacta/models/HoldingsDate.ts b/frontend/openapi/generated/pacta/models/HoldingsDate.ts
index 11c37ae..37c9d35 100644
--- a/frontend/openapi/generated/pacta/models/HoldingsDate.ts
+++ b/frontend/openapi/generated/pacta/models/HoldingsDate.ts
@@ -7,6 +7,6 @@ export type HoldingsDate = {
     /**
      * The time at which the holdings are represented at
      */
-    time: string;
+    time?: string;
 };
 
diff --git a/frontend/openapi/generated/pacta/models/IncompleteUpload.ts b/frontend/openapi/generated/pacta/models/IncompleteUpload.ts
index d02ba35..9e5146c 100644
--- a/frontend/openapi/generated/pacta/models/IncompleteUpload.ts
+++ b/frontend/openapi/generated/pacta/models/IncompleteUpload.ts
@@ -20,7 +20,7 @@ export type IncompleteUpload = {
      * Description of the upload
      */
     description: string;
-    propertyHoldingsDate?: HoldingsDate;
+    propertyHoldingsDate: HoldingsDate;
     /**
      * If set, this portfolio represents ESG data
      */
diff --git a/frontend/openapi/generated/pacta/models/Portfolio.ts b/frontend/openapi/generated/pacta/models/Portfolio.ts
index 729d843..2240c63 100644
--- a/frontend/openapi/generated/pacta/models/Portfolio.ts
+++ b/frontend/openapi/generated/pacta/models/Portfolio.ts
@@ -41,7 +41,7 @@ export type Portfolio = {
      * The list of initiatives that this portfolio is a member of
      */
     initiatives?: Array<PortfolioInitiativeMembershipInitiative>;
-    propertyHoldingsDate?: HoldingsDate;
+    propertyHoldingsDate: HoldingsDate;
     /**
      * If set, this portfolio represents ESG data
      */
diff --git a/frontend/openapi/generated/pacta/models/StartPortfolioUploadReq.ts b/frontend/openapi/generated/pacta/models/StartPortfolioUploadReq.ts
index ce128a1..8489ed3 100644
--- a/frontend/openapi/generated/pacta/models/StartPortfolioUploadReq.ts
+++ b/frontend/openapi/generated/pacta/models/StartPortfolioUploadReq.ts
@@ -9,7 +9,10 @@ import type { StartPortfolioUploadReqItem } from './StartPortfolioUploadReqItem'
 
 export type StartPortfolioUploadReq = {
     items: Array<StartPortfolioUploadReqItem>;
-    propertyHoldingsDate?: HoldingsDate;
+    /**
+     * The holdings date of the portfolio, if set
+     */
+    propertyHoldingsDate: HoldingsDate;
     /**
      * If set, this portfolio represents ESG data
      */
diff --git a/frontend/pages/upload.vue b/frontend/pages/upload.vue
index 07b3d49..5a73cf0 100644
--- a/frontend/pages/upload.vue
+++ b/frontend/pages/upload.vue
@@ -39,7 +39,7 @@ interface FileStateDetail extends FileState {
   effectiveError?: string | undefined
 }
 
-const holdingsDate = useState<HoldingsDate | undefined>(`${prefix}.holdingsDate`, () => undefined)
+const holdingsDate = useState<HoldingsDate>(`${prefix}.holdingsDate`, () => ({ time: undefined }))
 const esg = useState<OptionalBoolean>(`${prefix}.esg`, () => OptionalBoolean.OPTIONAL_BOOLEAN_UNSET)
 const external = useState<OptionalBoolean>(`${prefix}.external`, () => OptionalBoolean.OPTIONAL_BOOLEAN_UNSET)
 const engagementStrategy = useState<OptionalBoolean>(`${prefix}.engagementStrategy`, () => OptionalBoolean.OPTIONAL_BOOLEAN_UNSET)
@@ -50,7 +50,7 @@ const isProcessing = useState<boolean>(`${prefix}.isProcessing`, () => false)
 const fileStates = useState<FileState[]>(`${prefix}.fileState`, () => [])
 
 const reset = () => {
-  holdingsDate.value = undefined
+  holdingsDate.value = { time: undefined }
   esg.value = OptionalBoolean.OPTIONAL_BOOLEAN_UNSET
   external.value = OptionalBoolean.OPTIONAL_BOOLEAN_UNSET
   engagementStrategy.value = OptionalBoolean.OPTIONAL_BOOLEAN_UNSET
diff --git a/frontend/plugins/primevue.ts b/frontend/plugins/primevue.ts
index 1034938..e80e3ee 100644
--- a/frontend/plugins/primevue.ts
+++ b/frontend/plugins/primevue.ts
@@ -9,6 +9,8 @@ import Calendar from 'primevue/calendar'
 import Card from 'primevue/card'
 import Chips from 'primevue/chips'
 import Column from 'primevue/column'
+import ConfirmDialog from 'primevue/confirmdialog'
+import ConfirmationService from 'primevue/confirmationservice'
 import DataTable from 'primevue/datatable'
 import Dialog from 'primevue/dialog'
 import Dropdown from 'primevue/dropdown'
@@ -42,6 +44,7 @@ export default defineNuxtPlugin(({ vueApp }) => {
   vueApp.component('PVCard', Card)
   vueApp.component('PVChips', Chips)
   vueApp.component('PVColumn', Column)
+  vueApp.component('PVConfirmDialog', ConfirmDialog)
   vueApp.component('PVDataTable', DataTable)
   vueApp.component('PVDialog', Dialog)
   vueApp.component('PVDropdown', Dropdown)
@@ -62,4 +65,5 @@ export default defineNuxtPlugin(({ vueApp }) => {
   vueApp.component('PVTriStateCheckbox', TriStateCheckbox)
 
   vueApp.directive('tooltip', Tooltip)
+  vueApp.use(ConfirmationService)
 })
diff --git a/openapi/pacta.yaml b/openapi/pacta.yaml
index a1d8501..a703956 100644
--- a/openapi/pacta.yaml
+++ b/openapi/pacta.yaml
@@ -1508,6 +1508,7 @@ components:
       type: object
       required:
         - items
+        - propertyHoldingsDate
         - propertyESG
         - propertyExternal
         - propertyEngagementStrategy
@@ -1517,6 +1518,7 @@ components:
           items:
             $ref: '#/components/schemas/StartPortfolioUploadReqItem'
         propertyHoldingsDate:
+          description: The holdings date of the portfolio, if set
           $ref: '#/components/schemas/HoldingsDate'
         propertyESG:
           description: If set, this portfolio represents ESG data
@@ -1626,8 +1628,6 @@ components:
           description: The time at which the signed URL will expire. 
     HoldingsDate:
       type: object
-      required:
-        - time
       properties:
         time: 
           type: string 
@@ -1641,6 +1641,7 @@ components:
         - description
         - createdAt
         - adminDebugEnabled
+        - propertyHoldingsDate
         - propertyESG
         - propertyExternal
         - propertyEngagementStrategy
@@ -1708,6 +1709,7 @@ components:
         - createdAt
         - adminDebugEnabled
         - numberOfRows
+        - propertyHoldingsDate
         - propertyESG
         - propertyExternal
         - propertyEngagementStrategy