diff --git a/frontend/pages/email/new.vue b/frontend/pages/email/new.vue
index 9e66b48..c813582 100644
--- a/frontend/pages/email/new.vue
+++ b/frontend/pages/email/new.vue
@@ -1,6 +1,4 @@
 <script setup>
-const dataStore = useDataStore()
-const profileStore = useProfileStore()
 const route = useRoute()
 const router = useRouter()
 const toast = useToast()
@@ -22,6 +20,10 @@ const loadedDocuments = ref([])
 const loaded = ref(false)
 const noAccountsPresent = ref(false)
 const sourceMessage = ref(null)
+const recipientOptions = ref([])
+const selectedRecipient = ref(null)
+const loadingRecipients = ref(false)
+const preferredCustomerId = ref(null)
 const composeMode = computed(() => {
   const mode = String(route.query.mode || "")
   return ["reply", "replyAll", "forward"].includes(mode) ? mode : "new"
@@ -46,6 +48,160 @@ const formatAddress = (address) => {
 
 const formatAddressList = (addresses = []) => addresses.map(formatAddress).filter(Boolean).join(", ")
 
+const normalizeEmail = (value = "") => {
+  const text = String(value).trim()
+  const bracketMatch = text.match(/<([^<>]+)>/)
+  return String(bracketMatch?.[1] || text.split(/[;,]/)[0] || "").trim().toLowerCase()
+}
+
+const parseInfoData = (value) => {
+  if (!value) return {}
+  if (typeof value === "object") return value
+  try {
+    return JSON.parse(value)
+  } catch {
+    return {}
+  }
+}
+
+const addRecipientOption = (target, option) => {
+  const email = normalizeEmail(option.email)
+  if (!email) return
+
+  const existing = target.find(item => item.email === email)
+  if (existing) {
+    if (option.priority < existing.priority) Object.assign(existing, option, { email })
+    return
+  }
+
+  target.push({ ...option, email })
+}
+
+const syncSelectedRecipient = () => {
+  const currentValue = String(emailData.value.to || "").trim()
+  if (!currentValue) {
+    selectedRecipient.value = null
+    return
+  }
+
+  const currentEmail = normalizeEmail(currentValue)
+  const matchingOption = recipientOptions.value.find(option => option.email === currentEmail)
+  if (matchingOption && (currentValue.match(/@/g) || []).length === 1) {
+    selectedRecipient.value = matchingOption.value
+    return
+  }
+
+  const currentOption = {
+    label: `Aktuelle Empfänger · ${currentValue}`,
+    value: currentValue,
+    email: currentEmail,
+    priority: -2,
+  }
+  recipientOptions.value = [
+    currentOption,
+    ...recipientOptions.value.filter(option => option.value !== currentValue),
+  ]
+  selectedRecipient.value = currentValue
+}
+
+const loadRecipientOptions = async () => {
+  loadingRecipients.value = true
+
+  try {
+    const [customers, contacts] = await Promise.all([
+      useEntities("customers").select("*", "name", true),
+      useEntities("contacts").select("*, customer(id,name)", "fullName", true),
+    ])
+    const options = []
+    const customerNames = new Map(customers.map(customer => [Number(customer.id), customer.name]))
+
+    customers
+        .filter(customer => customer.active !== false)
+        .forEach(customer => {
+          const infoData = parseInfoData(customer.infoData)
+          const isPreferred = Number(customer.id) === Number(preferredCustomerId.value)
+          const priority = isPreferred ? 0 : 20
+
+          addRecipientOption(options, {
+            email: infoData.email,
+            value: infoData.email,
+            label: `${isPreferred ? "Passender Kunde" : "Kunde"} · ${customer.name} · ${infoData.email || ""}`,
+            priority,
+            customerId: Number(customer.id),
+            kind: "customer",
+          })
+          addRecipientOption(options, {
+            email: infoData.invoiceEmail,
+            value: infoData.invoiceEmail,
+            label: `${isPreferred ? "Passender Kunde" : "Kunde"} · ${customer.name} · Rechnung · ${infoData.invoiceEmail || ""}`,
+            priority: priority + 1,
+            customerId: Number(customer.id),
+            kind: "invoice",
+          })
+        })
+
+    contacts
+        .filter(contact => contact.active !== false && contact.email)
+        .forEach(contact => {
+          const customerId = Number(contact.customer?.id || contact.customer || 0)
+          const customerName = contact.customer?.name || customerNames.get(customerId)
+          const contactName = contact.fullName
+              || [contact.firstName, contact.lastName].filter(Boolean).join(" ")
+              || contact.email
+          const isPreferred = customerId && customerId === Number(preferredCustomerId.value)
+
+          addRecipientOption(options, {
+            email: contact.email,
+            value: formatAddress({ name: contactName, address: contact.email }),
+            label: [
+              isPreferred ? "Passender Ansprechpartner" : "Ansprechpartner",
+              contactName,
+              customerName,
+              contact.email,
+            ].filter(Boolean).join(" · "),
+            priority: isPreferred ? 2 : 30,
+            customerId,
+            kind: "contact",
+          })
+        })
+
+    if (!preferredCustomerId.value) {
+      const currentEmail = normalizeEmail(emailData.value.to)
+      preferredCustomerId.value = options.find(option => option.email === currentEmail)?.customerId || null
+    }
+
+    if (preferredCustomerId.value) {
+      options.forEach(option => {
+        if (Number(option.customerId) !== Number(preferredCustomerId.value)) return
+        option.priority = option.kind === "customer" ? 0 : option.kind === "invoice" ? 1 : 2
+        option.label = option.label
+            .replace(/^Kunde ·/, "Passender Kunde ·")
+            .replace(/^Ansprechpartner ·/, "Passender Ansprechpartner ·")
+      })
+    }
+
+    recipientOptions.value = options.sort((first, second) =>
+        first.priority - second.priority || first.label.localeCompare(second.label, "de")
+    )
+    syncSelectedRecipient()
+  } catch (err) {
+    recipientOptions.value = []
+    syncSelectedRecipient()
+    toast.add({
+      title: "Adressbuch konnte nicht geladen werden",
+      description: err?.data?.error || err?.message,
+      color: "warning",
+    })
+  } finally {
+    loadingRecipients.value = false
+  }
+}
+
+const selectRecipient = (value) => {
+  if (!value) return
+  emailData.value.to = value
+}
+
 const prefixedSubject = (prefix, subject = "") => {
   const cleanSubject = String(subject || "")
   return cleanSubject.toLowerCase().startsWith(prefix.toLowerCase()) ? cleanSubject : `${prefix} ${cleanSubject}`.trim()
@@ -124,38 +280,50 @@ const setupPage = async () => {
 
 
     if(route.query.loadDocuments) {
-      console.log(JSON.parse(route.query.loadDocuments))
       const data = await useFiles().selectSomeDocuments(JSON.parse(route.query.loadDocuments))
-      console.log(data)
 
       if(data) loadedDocuments.value = data
 
       loadedDocuments.value = await Promise.all(loadedDocuments.value.map(async doc => {
 
         const document = await useEntities("createddocuments").selectSingle(doc.createddocument)
-        console.log(document)
         return {
           ...doc,
           createddocument: document
         }}))
 
-      //console.log(loadedDocuments.value)
-
       if(loadedDocuments.value.length > 0) {
-        console.log(loadedDocuments.value[0])
-        emailData.value.subject = `${loadedDocuments.value[0].createddocument.title} von ${auth.activeTenantData.businessInfo.name}`
+        const createdDocument = loadedDocuments.value[0].createddocument
+        const customerId = Number(createdDocument.customer?.id || createdDocument.customer || 0) || null
+        const contactId = Number(createdDocument.contact?.id || createdDocument.contact || 0) || null
+        const customer = createdDocument.customer && typeof createdDocument.customer === "object"
+            ? createdDocument.customer
+            : customerId
+                ? await useEntities("customers").selectSingle(customerId)
+                : null
+        const contact = createdDocument.contact && typeof createdDocument.contact === "object"
+            ? createdDocument.contact
+            : contactId
+                ? await useEntities("contacts").selectSingle(contactId)
+                : null
 
-        if(loadedDocuments.value[0].createddocument.contact && loadedDocuments.value[0].createddocument.contact.email) {
-          console.log("Contact")
-          emailData.value.to = loadedDocuments.value[0].createddocument.contact.email
-        } else if(loadedDocuments.value[0].createddocument.customer && loadedDocuments.value[0].createddocument.customer.infoData.invoiceEmail) {
-          emailData.value.to = loadedDocuments.value[0].createddocument.customer.infoData.invoiceEmail
-        } else if(loadedDocuments.value[0].createddocument.customer && loadedDocuments.value[0].createddocument.customer.infoData.email) {
-          emailData.value.to = loadedDocuments.value[0].createddocument.customer.infoData.email
+        preferredCustomerId.value = customerId || Number(contact?.customer?.id || contact?.customer || 0) || null
+        emailData.value.subject = `${createdDocument.title} von ${auth.activeTenantData.businessInfo.name}`
+
+        if(contact?.email) {
+          emailData.value.to = formatAddress({
+            name: contact.fullName,
+            address: contact.email,
+          })
+        } else if(parseInfoData(customer?.infoData).invoiceEmail) {
+          emailData.value.to = parseInfoData(customer.infoData).invoiceEmail
+        } else if(parseInfoData(customer?.infoData).email) {
+          emailData.value.to = parseInfoData(customer.infoData).email
         }
       }
     }
 
+    await loadRecipientOptions()
     loaded.value = true
   }
 
@@ -311,10 +479,28 @@ const sendEmail = async () => {
           <UFormField
               label="Empfänger"
           >
-            <UInput
-                class="w-full my-1"
-                v-model="emailData.to"
-            />
+            <div class="grid gap-2 md:grid-cols-[minmax(260px,0.9fr)_minmax(320px,1.1fr)]">
+              <USelectMenu
+                  v-model="selectedRecipient"
+                  :items="recipientOptions"
+                  value-key="value"
+                  label-key="label"
+                  :loading="loadingRecipients"
+                  :search-input="{ placeholder: 'Kunde, Ansprechpartner oder E-Mail suchen' }"
+                  placeholder="Aus Kunden und Ansprechpartnern wählen"
+                  class="w-full"
+                  @update:model-value="selectRecipient"
+              />
+              <UInput
+                  class="w-full"
+                  v-model="emailData.to"
+                  placeholder="E-Mail-Adresse oder mehrere Adressen"
+                  @update:model-value="selectedRecipient = null"
+              />
+            </div>
+            <p class="mt-1 text-xs text-dimmed">
+              Passende Adressen zum vorausgefüllten Kunden werden zuerst angezeigt. Freie Eingaben bleiben möglich.
+            </p>
           </UFormField>
           <UFormField
               label="Kopie"