diff --git a/js/components/upload_input.js b/js/components/upload_input.js
index 6a1db083..a7ef694e 100644
--- a/js/components/upload_input.js
+++ b/js/components/upload_input.js
@@ -46,9 +46,9 @@ export default {
     return {
       hasInitialData: !!this.initialData,
       attachment: this.initialData || null,
-      showErrors: this.initialErrors,
       changed: false,
-      uploadError: null,
+      uploadError: false,
+      sizeError: false,
     }
   },
 
@@ -63,15 +63,22 @@ export default {
 
   methods: {
     addAttachment: async function(e) {
+      this.clearErrors()
+
       const file = e.target.files[0]
+      if (file.size > 64000000) {
+        this.sizeError = true
+        return
+      }
+
       const response = await this.uploader.upload(file, this.objectName)
+
       if (response.ok) {
         this.attachment = e.target.value
         this.$refs.attachmentFilename.value = file.name
         this.$refs.attachmentObjectName.value = this.objectName
         this.$refs.attachmentInput.disabled = true
       } else {
-        this.showErrors = true
         this.uploadError = true
       }
 
@@ -91,8 +98,7 @@ export default {
         this.$refs.attachmentInput.value = null
         this.$refs.attachmentInput.disabled = false
       }
-      this.showErrors = false
-      this.uploadError = false
+      this.clearErrors()
       this.changed = true
 
       emitEvent('field-change', this, {
@@ -101,6 +107,10 @@ export default {
         watch: this.watch,
       })
     },
+    clearErrors: function() {
+      this.uploadError = false
+      this.sizeError = false
+    }
   },
 
   computed: {
@@ -115,5 +125,8 @@ export default {
     hideInput: function() {
       return this.hasInitialData && !this.changed
     },
+    showErrors: function() {
+      return (!this.changed && this.initialErrors) || this.uploadError || this.sizeError
+    }
   },
 }
diff --git a/templates/components/upload_input.html b/templates/components/upload_input.html
index a56cb0bf..a261ea21 100644
--- a/templates/components/upload_input.html
+++ b/templates/components/upload_input.html
@@ -46,6 +46,9 @@
       <template v-if="uploadError">
         <span class="usa-input__message">{{ "forms.task_order.upload_error" | translate }}</span>
       </template>
+      <template v-if="sizeError">
+        <span class="usa-input__message">{{ "forms.task_order.size_error" | translate }}</span>
+      </template>
       {% for error, error_messages in field.errors.items() %}
         <span class="usa-input__message">{{error_messages[0]}}</span>
       {% endfor %}
diff --git a/translations.yaml b/translations.yaml
index 1e13a8f9..7937bb96 100644
--- a/translations.yaml
+++ b/translations.yaml
@@ -156,6 +156,7 @@ forms:
       length_error: Filename may be no longer than 100 characters.
   task_order:
     upload_error: There was an error uploading your file. Please try again. If you encounter repeated problems uploading this file, please contact CCPO.
+    size_error: The file you have selected is too large. Please choose a file no larger than 64MB.
     app_migration:
       both: 'Yes, migrating from both an on-premise data center <strong>and</strong> another cloud provider'
       cloud: 'Yes, migrating from another cloud provider'