diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/api/SendsApi.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/api/SendsApi.kt
index eed47da82..102ff6a5e 100644
--- a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/api/SendsApi.kt
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/api/SendsApi.kt
@@ -1,7 +1,7 @@
 package com.x8bit.bitwarden.data.vault.datasource.network.api
 
 import androidx.annotation.Keep
-import com.x8bit.bitwarden.data.vault.datasource.network.model.SendFileResponseJson
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SendJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SyncResponseJson
 import okhttp3.MultipartBody
@@ -28,7 +28,7 @@ interface SendsApi {
      * Create a file send.
      */
     @POST("sends/file/v2")
-    suspend fun createFileSend(@Body body: SendJsonRequest): Result<SendFileResponseJson>
+    suspend fun createFileSend(@Body body: SendJsonRequest): Result<CreateFileSendResponseJson>
 
     /**
      * Updates a send.
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateFileSendResponse.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateFileSendResponse.kt
new file mode 100644
index 000000000..e37b4c1be
--- /dev/null
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateFileSendResponse.kt
@@ -0,0 +1,36 @@
+package com.x8bit.bitwarden.data.vault.datasource.network.model
+
+import kotlinx.serialization.SerialName
+import kotlinx.serialization.Serializable
+
+/**
+ * Represents a response from create file send.
+ */
+sealed class CreateFileSendResponse {
+
+    /**
+     * Represents the response from a successful create file send request.
+     *
+     * @property createFileJsonResponse Response JSON received from create file send request.
+     */
+    data class Success(
+        val createFileJsonResponse: CreateFileSendResponseJson,
+    ) : CreateFileSendResponse()
+
+    /**
+     * Represents the json body of an invalid create request.
+     *
+     * @property message A general, user-displayable error message.
+     * @property validationErrors a map where each value is a list of error messages for each
+     * key. The values in the array should be used for display to the user, since the keys tend
+     * to come back as nonsense. (eg: empty string key)
+     */
+    @Serializable
+    data class Invalid(
+        @SerialName("message")
+        override val message: String,
+
+        @SerialName("validationErrors")
+        override val validationErrors: Map<String, List<String>>?,
+    ) : CreateFileSendResponse(), InvalidJsonResponse
+}
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/SendFileResponseJson.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateFileSendResponseJson.kt
similarity index 91%
rename from app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/SendFileResponseJson.kt
rename to app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateFileSendResponseJson.kt
index 0d6f1d90c..2baa66602 100644
--- a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/SendFileResponseJson.kt
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateFileSendResponseJson.kt
@@ -7,7 +7,7 @@ import kotlinx.serialization.Serializable
  * Represents the JSON response from creating a new file send.
  */
 @Serializable
-data class SendFileResponseJson(
+data class CreateFileSendResponseJson(
     @SerialName("url")
     val url: String,
 
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateSendJsonResponse.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateSendJsonResponse.kt
new file mode 100644
index 000000000..b686967e9
--- /dev/null
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/CreateSendJsonResponse.kt
@@ -0,0 +1,34 @@
+package com.x8bit.bitwarden.data.vault.datasource.network.model
+
+import kotlinx.serialization.SerialName
+import kotlinx.serialization.Serializable
+
+/**
+ * Models a response from either "create text send" or "create file send" requests.
+ */
+sealed class CreateSendJsonResponse {
+    /**
+     * Represents a successful response from either "create text send" or "create file send"
+     * request.
+     *
+     * @property send The created send object.
+     */
+    data class Success(val send: SyncResponseJson.Send) : CreateSendJsonResponse()
+
+    /**
+     * Represents the json body of an invalid create request.
+     *
+     * @property message A general, user-displayable error message.
+     * @property validationErrors a map where each value is a list of error messages for each
+     * key. The values in the array should be used for display to the user, since the keys tend
+     * to come back as nonsense. (eg: empty string key)
+     */
+    @Serializable
+    data class Invalid(
+        @SerialName("message")
+        override val message: String,
+
+        @SerialName("validationErrors")
+        override val validationErrors: Map<String, List<String>>?,
+    ) : CreateSendJsonResponse(), InvalidJsonResponse
+}
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/InvalidJsonResponse.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/InvalidJsonResponse.kt
new file mode 100644
index 000000000..61451923e
--- /dev/null
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/model/InvalidJsonResponse.kt
@@ -0,0 +1,28 @@
+package com.x8bit.bitwarden.data.vault.datasource.network.model
+
+/**
+ * Represents the json body of an invalid send json request.
+ */
+sealed interface InvalidJsonResponse {
+
+    /**
+     * A general, user-displayable error message.
+     */
+    val message: String
+
+    /**
+     * a map where each value is a list of error messages for each key.
+     * The values in the array should be used for display to the user, since the keys tend to come
+     * back as nonsense. (eg: empty string key)
+     */
+    val validationErrors: Map<String, List<String>>?
+
+    /**
+     * Returns the first error message found in [validationErrors], or [message] if there are no
+     * [validationErrors] present.
+     */
+    val firstValidationErrorMessage: String?
+        get() = validationErrors
+            ?.flatMap { it.value }
+            ?.first()
+}
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsService.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsService.kt
index 7382d5ea3..990217308 100644
--- a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsService.kt
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsService.kt
@@ -1,6 +1,8 @@
 package com.x8bit.bitwarden.data.vault.datasource.network.service
 
-import com.x8bit.bitwarden.data.vault.datasource.network.model.SendFileResponseJson
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponse
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponseJson
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateSendJsonResponse
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SendJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SyncResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.UpdateSendResponseJson
@@ -14,20 +16,20 @@ interface SendsService {
      */
     suspend fun createTextSend(
         body: SendJsonRequest,
-    ): Result<SyncResponseJson.Send>
+    ): Result<CreateSendJsonResponse>
 
     /**
      * Attempt to create a file send.
      */
     suspend fun createFileSend(
         body: SendJsonRequest,
-    ): Result<SendFileResponseJson>
+    ): Result<CreateFileSendResponse>
 
     /**
      * Attempt to upload the given [encryptedFile] associated with the [sendFileResponse].
      */
     suspend fun uploadFile(
-        sendFileResponse: SendFileResponseJson,
+        sendFileResponse: CreateFileSendResponseJson,
         encryptedFile: ByteArray,
     ): Result<SyncResponseJson.Send>
 
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceImpl.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceImpl.kt
index 2a6b97ec4..5e6091b15 100644
--- a/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceImpl.kt
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceImpl.kt
@@ -5,8 +5,10 @@ import com.x8bit.bitwarden.data.platform.datasource.network.model.toBitwardenErr
 import com.x8bit.bitwarden.data.platform.datasource.network.util.parseErrorBodyOrNull
 import com.x8bit.bitwarden.data.vault.datasource.network.api.AzureApi
 import com.x8bit.bitwarden.data.vault.datasource.network.api.SendsApi
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponse
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponseJson
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateSendJsonResponse
 import com.x8bit.bitwarden.data.vault.datasource.network.model.FileUploadType
-import com.x8bit.bitwarden.data.vault.datasource.network.model.SendFileResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SendJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SyncResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.UpdateSendResponseJson
@@ -28,11 +30,33 @@ class SendsServiceImpl(
     private val clock: Clock,
     private val json: Json,
 ) : SendsService {
-    override suspend fun createTextSend(body: SendJsonRequest): Result<SyncResponseJson.Send> =
+    override suspend fun createTextSend(
+        body: SendJsonRequest,
+    ): Result<CreateSendJsonResponse> =
         sendsApi.createTextSend(body = body)
+            .map { CreateSendJsonResponse.Success(send = it) }
+            .recoverCatching { throwable ->
+                throwable.toBitwardenError()
+                    .parseErrorBodyOrNull<CreateSendJsonResponse.Invalid>(
+                        code = 400,
+                        json = json,
+                    )
+                    ?: throw throwable
+            }
 
-    override suspend fun createFileSend(body: SendJsonRequest): Result<SendFileResponseJson> =
+    override suspend fun createFileSend(
+        body: SendJsonRequest,
+    ): Result<CreateFileSendResponse> =
         sendsApi.createFileSend(body = body)
+            .map { CreateFileSendResponse.Success(it) }
+            .recoverCatching { throwable ->
+                throwable.toBitwardenError()
+                    .parseErrorBodyOrNull<CreateFileSendResponse.Invalid>(
+                        code = 400,
+                        json = json,
+                    )
+                    ?: throw throwable
+            }
 
     override suspend fun updateSend(
         sendId: String,
@@ -55,7 +79,7 @@ class SendsServiceImpl(
             }
 
     override suspend fun uploadFile(
-        sendFileResponse: SendFileResponseJson,
+        sendFileResponse: CreateFileSendResponseJson,
         encryptedFile: ByteArray,
     ): Result<SyncResponseJson.Send> {
         val send = sendFileResponse.sendResponse
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryImpl.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryImpl.kt
index 76d9a352a..360a8e89b 100644
--- a/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryImpl.kt
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryImpl.kt
@@ -10,6 +10,7 @@ import com.bitwarden.core.ExportFormat
 import com.bitwarden.core.FolderView
 import com.bitwarden.core.InitOrgCryptoRequest
 import com.bitwarden.core.InitUserCryptoMethod
+import com.bitwarden.core.Send
 import com.bitwarden.core.SendType
 import com.bitwarden.core.SendView
 import com.bitwarden.crypto.Kdf
@@ -35,10 +36,13 @@ import com.x8bit.bitwarden.data.platform.repository.util.map
 import com.x8bit.bitwarden.data.platform.repository.util.observeWhenSubscribedAndLoggedIn
 import com.x8bit.bitwarden.data.platform.repository.util.updateToPendingOrLoading
 import com.x8bit.bitwarden.data.platform.util.asFailure
+import com.x8bit.bitwarden.data.platform.util.asSuccess
 import com.x8bit.bitwarden.data.platform.util.flatMap
 import com.x8bit.bitwarden.data.vault.datasource.disk.VaultDiskSource
 import com.x8bit.bitwarden.data.vault.datasource.network.model.AttachmentJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateCipherInOrganizationJsonRequest
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponse
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateSendJsonResponse
 import com.x8bit.bitwarden.data.vault.datasource.network.model.ShareCipherJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SyncResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.UpdateCipherCollectionsJsonRequest
@@ -980,11 +984,12 @@ class VaultRepositoryImpl(
             )
     }
 
+    @Suppress("ReturnCount")
     override suspend fun createSend(
         sendView: SendView,
         fileUri: Uri?,
     ): CreateSendResult {
-        val userId = activeUserId ?: return CreateSendResult.Error
+        val userId = activeUserId ?: return CreateSendResult.Error(message = null)
         return vaultSdkSource
             .encryptSend(
                 userId = userId,
@@ -992,54 +997,33 @@ class VaultRepositoryImpl(
             )
             .flatMap { send ->
                 when (send.type) {
-                    SendType.TEXT -> {
-                        sendsService.createTextSend(body = send.toEncryptedNetworkSend())
+                    SendType.TEXT -> sendsService.createTextSend(send.toEncryptedNetworkSend())
+                    SendType.FILE -> createFileSend(fileUri, userId, send)
+                }
+            }
+            .map { createSendResponse ->
+                when (createSendResponse) {
+                    is CreateSendJsonResponse.Invalid -> {
+                        return CreateSendResult.Error(
+                            message = createSendResponse.firstValidationErrorMessage,
+                        )
                     }
 
-                    SendType.FILE -> {
-                        val uri = fileUri ?: return@flatMap IllegalArgumentException(
-                            "File URI must be present to create a File Send.",
-                        )
-                            .asFailure()
-
-                        fileManager
-                            .uriToByteArray(fileUri = uri)
-                            .flatMap {
-                                vaultSdkSource.encryptBuffer(
-                                    userId = userId,
-                                    send = send,
-                                    fileBuffer = it,
-                                )
-                            }
-                            .flatMap { encryptedFile ->
-                                sendsService
-                                    .createFileSend(
-                                        body = send.toEncryptedNetworkSend(
-                                            fileLength = encryptedFile.size,
-                                        ),
-                                    )
-                                    .flatMap { sendFileResponse ->
-                                        sendsService.uploadFile(
-                                            sendFileResponse = sendFileResponse,
-                                            encryptedFile = encryptedFile,
-                                        )
-                                    }
-                            }
+                    is CreateSendJsonResponse.Success -> {
+                        // Save the send immediately, regardless of whether the decrypt succeeds
+                        vaultDiskSource.saveSend(userId = userId, send = createSendResponse.send)
+                        createSendResponse
                     }
                 }
             }
-            .onSuccess {
-                // Save the send immediately, regardless of whether the decrypt succeeds
-                vaultDiskSource.saveSend(userId = userId, send = it)
-            }
-            .flatMap {
+            .flatMap { createSendSuccessResponse ->
                 vaultSdkSource.decryptSend(
                     userId = userId,
-                    send = it.toEncryptedSdkSend(),
+                    send = createSendSuccessResponse.send.toEncryptedSdkSend(),
                 )
             }
             .fold(
-                onFailure = { CreateSendResult.Error },
+                onFailure = { CreateSendResult.Error(message = null) },
                 onSuccess = { CreateSendResult.Success(it) },
             )
     }
@@ -1594,6 +1578,56 @@ class VaultRepositoryImpl(
             )
     }
 
+    private suspend fun createFileSend(
+        uri: Uri?,
+        userId: String,
+        send: Send,
+    ): Result<CreateSendJsonResponse> {
+        uri ?: return IllegalArgumentException(
+            "File URI must be present to create a File Send.",
+        )
+            .asFailure()
+
+        return fileManager
+            .uriToByteArray(fileUri = uri)
+            .flatMap {
+                vaultSdkSource.encryptBuffer(
+                    userId = userId,
+                    send = send,
+                    fileBuffer = it,
+                )
+            }
+            .flatMap { encryptedFile ->
+                sendsService
+                    .createFileSend(
+                        body = send.toEncryptedNetworkSend(
+                            fileLength = encryptedFile.size,
+                        ),
+                    )
+                    .flatMap { sendFileResponse ->
+                        when (sendFileResponse) {
+                            is CreateFileSendResponse.Invalid -> {
+                                CreateSendJsonResponse
+                                    .Invalid(
+                                        message = sendFileResponse.message,
+                                        validationErrors = sendFileResponse.validationErrors,
+                                    )
+                                    .asSuccess()
+                            }
+
+                            is CreateFileSendResponse.Success -> {
+                                sendsService
+                                    .uploadFile(
+                                        sendFileResponse = sendFileResponse.createFileJsonResponse,
+                                        encryptedFile = encryptedFile,
+                                    )
+                                    .map { CreateSendJsonResponse.Success(it) }
+                            }
+                        }
+                    }
+            }
+    }
+
     /**
      * Deletes the send specified by [syncSendDeleteData] from disk.
      */
diff --git a/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/model/CreateSendResult.kt b/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/model/CreateSendResult.kt
index b7f604827..d1ccb9b45 100644
--- a/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/model/CreateSendResult.kt
+++ b/app/src/main/java/com/x8bit/bitwarden/data/vault/repository/model/CreateSendResult.kt
@@ -15,5 +15,5 @@ sealed class CreateSendResult {
     /**
      * Generic error while creating a send.
      */
-    data object Error : CreateSendResult()
+    data class Error(val message: String?) : CreateSendResult()
 }
diff --git a/app/src/main/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModel.kt b/app/src/main/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModel.kt
index adf1da50c..43c26a792 100644
--- a/app/src/main/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModel.kt
+++ b/app/src/main/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModel.kt
@@ -184,12 +184,13 @@ class AddSendViewModel @Inject constructor(
         action: AddSendAction.Internal.CreateSendResultReceive,
     ) {
         when (val result = action.result) {
-            CreateSendResult.Error -> {
+            is CreateSendResult.Error -> {
                 mutableStateFlow.update {
                     it.copy(
                         dialogState = AddSendState.DialogState.Error(
                             title = R.string.an_error_has_occurred.asText(),
-                            message = R.string.generic_error_message.asText(),
+                            message = result.message?.asText()
+                                ?: R.string.generic_error_message.asText(),
                         ),
                     )
                 }
diff --git a/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/model/SyncResponseSendUtil.kt b/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/model/SyncResponseSendUtil.kt
index 5cec0df8a..eb529c39a 100644
--- a/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/model/SyncResponseSendUtil.kt
+++ b/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/model/SyncResponseSendUtil.kt
@@ -2,6 +2,13 @@ package com.x8bit.bitwarden.data.vault.datasource.network.model
 
 import java.time.ZonedDateTime
 
+fun createMockFileSendResponseJson(number: Int, type: SendTypeJson = SendTypeJson.FILE) =
+    CreateFileSendResponseJson(
+        url = "www.test.com",
+        fileUploadType = FileUploadType.AZURE,
+        sendResponse = createMockSend(number = number, type = type),
+    )
+
 fun createMockSend(
     number: Int,
     type: SendTypeJson = SendTypeJson.FILE,
diff --git a/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceTest.kt b/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceTest.kt
index e20306624..3fdd73e51 100644
--- a/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceTest.kt
+++ b/app/src/test/java/com/x8bit/bitwarden/data/vault/datasource/network/service/SendsServiceTest.kt
@@ -4,10 +4,11 @@ import android.net.Uri
 import com.x8bit.bitwarden.data.platform.base.BaseServiceTest
 import com.x8bit.bitwarden.data.vault.datasource.network.api.AzureApi
 import com.x8bit.bitwarden.data.vault.datasource.network.api.SendsApi
-import com.x8bit.bitwarden.data.vault.datasource.network.model.FileUploadType
-import com.x8bit.bitwarden.data.vault.datasource.network.model.SendFileResponseJson
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponse
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateSendJsonResponse
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SendTypeJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.UpdateSendResponseJson
+import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockFileSendResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockSend
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockSendJsonRequest
 import io.mockk.every
@@ -52,16 +53,18 @@ class SendsServiceTest : BaseServiceTest() {
 
     @Test
     fun `createFileSend should return the correct response`() = runTest {
-        val response = SendFileResponseJson(
-            url = "www.test.com",
-            fileUploadType = FileUploadType.AZURE,
-            sendResponse = createMockSend(number = 1, type = SendTypeJson.FILE),
+        val sendFileResponse = CreateFileSendResponse.Success(
+            createFileJsonResponse = createMockFileSendResponseJson(number = 1),
         )
         server.enqueue(MockResponse().setBody(CREATE_FILE_SEND_SUCCESS_JSON))
         val result = sendsService.createFileSend(
             body = createMockSendJsonRequest(number = 1, type = SendTypeJson.FILE),
         )
-        assertEquals(response, result.getOrThrow())
+
+        assertEquals(
+            sendFileResponse,
+            result.getOrThrow(),
+        )
     }
 
     @Test
@@ -71,7 +74,7 @@ class SendsServiceTest : BaseServiceTest() {
             body = createMockSendJsonRequest(number = 1, type = SendTypeJson.TEXT),
         )
         assertEquals(
-            createMockSend(number = 1),
+            CreateSendJsonResponse.Success(createMockSend(number = 1)),
             result.getOrThrow(),
         )
     }
@@ -113,13 +116,9 @@ class SendsServiceTest : BaseServiceTest() {
     fun `uploadFile with Azure uploadFile success should return send`() = runTest {
         val url = "www.test.com"
         setupMockUri(url = url, queryParams = mapOf("sv" to "2024-04-03"))
-        val mockSend = createMockSend(number = 1, type = SendTypeJson.FILE)
-        val sendFileResponse = SendFileResponseJson(
-            url = url,
-            fileUploadType = FileUploadType.AZURE,
-            sendResponse = mockSend,
-        )
+        val sendFileResponse = createMockFileSendResponseJson(number = 1)
         val encryptedFile = byteArrayOf()
+
         server.enqueue(MockResponse().setResponseCode(201))
 
         val result = sendsService.uploadFile(
@@ -127,17 +126,14 @@ class SendsServiceTest : BaseServiceTest() {
             encryptedFile = encryptedFile,
         )
 
-        assertEquals(mockSend, result.getOrThrow())
+        assertEquals(sendFileResponse.sendResponse, result.getOrThrow())
     }
 
     @Test
     fun `uploadFile with Direct uploadFile success should return send`() = runTest {
-        val mockSend = createMockSend(number = 1, type = SendTypeJson.FILE)
-        val sendFileResponse = SendFileResponseJson(
-            url = "www.test.com",
-            fileUploadType = FileUploadType.DIRECT,
-            sendResponse = mockSend,
-        )
+        val url = "www.test.com"
+        setupMockUri(url = url, queryParams = mapOf("sv" to "2024-04-03"))
+        val sendFileResponse = createMockFileSendResponseJson(number = 1)
         val encryptedFile = byteArrayOf()
         server.enqueue(MockResponse().setResponseCode(201))
 
@@ -146,7 +142,7 @@ class SendsServiceTest : BaseServiceTest() {
             encryptedFile = encryptedFile,
         )
 
-        assertEquals(mockSend, result.getOrThrow())
+        assertEquals(sendFileResponse.sendResponse, result.getOrThrow())
     }
 
     @Test
diff --git a/app/src/test/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryTest.kt b/app/src/test/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryTest.kt
index 847df88c1..31ea74484 100644
--- a/app/src/test/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryTest.kt
+++ b/app/src/test/java/com/x8bit/bitwarden/data/vault/repository/VaultRepositoryTest.kt
@@ -39,9 +39,9 @@ import com.x8bit.bitwarden.data.platform.util.asSuccess
 import com.x8bit.bitwarden.data.vault.datasource.disk.VaultDiskSource
 import com.x8bit.bitwarden.data.vault.datasource.network.model.AttachmentJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateCipherInOrganizationJsonRequest
-import com.x8bit.bitwarden.data.vault.datasource.network.model.FileUploadType
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateFileSendResponse
+import com.x8bit.bitwarden.data.vault.datasource.network.model.CreateSendJsonResponse
 import com.x8bit.bitwarden.data.vault.datasource.network.model.FolderJsonRequest
-import com.x8bit.bitwarden.data.vault.datasource.network.model.SendFileResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SendTypeJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.ShareCipherJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.SyncResponseJson
@@ -55,6 +55,7 @@ import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockCipher
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockCipherJsonRequest
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockCollection
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockDomains
+import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockFileSendResponseJson
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockFolder
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockOrganization
 import com.x8bit.bitwarden.data.vault.datasource.network.model.createMockOrganizationKeys
@@ -2430,7 +2431,7 @@ class VaultRepositoryTest {
             )
 
             assertEquals(
-                CreateSendResult.Error,
+                CreateSendResult.Error(message = null),
                 result,
             )
         }
@@ -2447,7 +2448,7 @@ class VaultRepositoryTest {
 
             val result = vaultRepository.createSend(sendView = mockSendView, fileUri = null)
 
-            assertEquals(CreateSendResult.Error, result)
+            assertEquals(CreateSendResult.Error(message = null), result)
         }
 
     @Test
@@ -2469,7 +2470,7 @@ class VaultRepositoryTest {
 
             val result = vaultRepository.createSend(sendView = mockSendView, fileUri = null)
 
-            assertEquals(CreateSendResult.Error, result)
+            assertEquals(CreateSendResult.Error(IllegalStateException().message), result)
         }
 
     @Suppress("MaxLineLength")
@@ -2482,6 +2483,7 @@ class VaultRepositoryTest {
             val mockSdkSend = createMockSdkSend(number = 1, type = SendType.TEXT)
             val mockSend = createMockSend(number = 1, type = SendTypeJson.TEXT)
             val mockSendViewResult = createMockSendView(number = 2)
+            val sendTextResponse = CreateSendJsonResponse.Success(send = mockSend)
             coEvery {
                 vaultSdkSource.encryptSend(userId = userId, sendView = mockSendView)
             } returns mockSdkSend.asSuccess()
@@ -2490,7 +2492,7 @@ class VaultRepositoryTest {
                     body = createMockSendJsonRequest(number = 1, type = SendTypeJson.TEXT)
                         .copy(fileLength = null),
                 )
-            } returns mockSend.asSuccess()
+            } returns sendTextResponse.asSuccess()
             coEvery { vaultDiskSource.saveSend(userId, mockSend) } just runs
             coEvery {
                 vaultSdkSource.decryptSend(userId, mockSdkSend)
@@ -2529,7 +2531,7 @@ class VaultRepositoryTest {
 
             val result = vaultRepository.createSend(sendView = mockSendView, fileUri = uri)
 
-            assertEquals(CreateSendResult.Error, result)
+            assertEquals(CreateSendResult.Error(IllegalStateException().message), result)
         }
 
     @Test
@@ -2544,14 +2546,18 @@ class VaultRepositoryTest {
             val mockSdkSend = createMockSdkSend(number = 1)
             val byteArray = byteArrayOf(1)
             val encryptedByteArray = byteArrayOf(2)
-            val sendFileResponse = SendFileResponseJson(
-                url = url,
-                fileUploadType = FileUploadType.AZURE,
-                sendResponse = createMockSend(number = 1, type = SendTypeJson.FILE),
+            val sendFileResponse = CreateFileSendResponse.Success(
+                createMockFileSendResponseJson(
+                    number = 1,
+                    type = SendTypeJson.FILE,
+                ),
             )
             coEvery {
                 vaultSdkSource.encryptSend(userId = userId, sendView = mockSendView)
             } returns mockSdkSend.asSuccess()
+            coEvery {
+                vaultSdkSource.decryptSend(userId, mockSdkSend)
+            } returns mockSendView.asSuccess()
             coEvery { fileManager.uriToByteArray(any()) } returns byteArray.asSuccess()
             coEvery {
                 vaultSdkSource.encryptBuffer(
@@ -2560,19 +2566,25 @@ class VaultRepositoryTest {
                     fileBuffer = byteArray,
                 )
             } returns encryptedByteArray.asSuccess()
+            coEvery {
+                vaultDiskSource.saveSend(
+                    userId,
+                    sendFileResponse.createFileJsonResponse.sendResponse,
+                )
+            } just runs
             coEvery {
                 sendsService.createFileSend(body = createMockSendJsonRequest(number = 1))
             } returns sendFileResponse.asSuccess()
             coEvery {
                 sendsService.uploadFile(
-                    sendFileResponse = sendFileResponse,
+                    sendFileResponse = sendFileResponse.createFileJsonResponse,
                     encryptedFile = encryptedByteArray,
                 )
-            } returns Throwable("Fail").asFailure()
+            } returns Throwable().asFailure()
 
             val result = vaultRepository.createSend(sendView = mockSendView, fileUri = uri)
 
-            assertEquals(CreateSendResult.Error, result)
+            assertEquals(CreateSendResult.Error(null), result)
         }
 
     @Test
@@ -2588,11 +2600,11 @@ class VaultRepositoryTest {
             coEvery {
                 vaultSdkSource.encryptSend(userId = userId, sendView = mockSendView)
             } returns mockSdkSend.asSuccess()
-            coEvery { fileManager.uriToByteArray(any()) } returns Throwable("Fail").asFailure()
+            coEvery { fileManager.uriToByteArray(any()) } returns Throwable().asFailure()
 
             val result = vaultRepository.createSend(sendView = mockSendView, fileUri = uri)
 
-            assertEquals(CreateSendResult.Error, result)
+            assertEquals(CreateSendResult.Error(message = null), result)
         }
 
     @Test
@@ -2607,11 +2619,8 @@ class VaultRepositoryTest {
             val mockSdkSend = createMockSdkSend(number = 1)
             val byteArray = byteArrayOf(1)
             val encryptedByteArray = byteArrayOf(2)
-            val sendResponse = createMockSend(number = 1)
-            val sendFileResponse = SendFileResponseJson(
-                url = url,
-                fileUploadType = FileUploadType.AZURE,
-                sendResponse = sendResponse,
+            val sendFileResponse = CreateFileSendResponse.Success(
+                createMockFileSendResponseJson(number = 1),
             )
             val mockSendViewResult = createMockSendView(number = 1)
             coEvery {
@@ -2630,11 +2639,16 @@ class VaultRepositoryTest {
             } returns sendFileResponse.asSuccess()
             coEvery {
                 sendsService.uploadFile(
-                    sendFileResponse = sendFileResponse,
+                    sendFileResponse = sendFileResponse.createFileJsonResponse,
                     encryptedFile = encryptedByteArray,
                 )
-            } returns sendResponse.asSuccess()
-            coEvery { vaultDiskSource.saveSend(userId, sendResponse) } just runs
+            } returns sendFileResponse.createFileJsonResponse.sendResponse.asSuccess()
+            coEvery {
+                vaultDiskSource.saveSend(
+                    userId,
+                    sendFileResponse.createFileJsonResponse.sendResponse,
+                )
+            } just runs
             coEvery {
                 vaultSdkSource.decryptSend(userId, mockSdkSend)
             } returns mockSendViewResult.asSuccess()
diff --git a/app/src/test/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModelTest.kt b/app/src/test/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModelTest.kt
index 43d8ce96d..2a60c67c1 100644
--- a/app/src/test/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModelTest.kt
+++ b/app/src/test/java/com/x8bit/bitwarden/ui/tools/feature/send/addsend/AddSendViewModelTest.kt
@@ -259,7 +259,7 @@ class AddSendViewModelTest : BaseViewModelTest() {
         every { viewState.toSendView(clock) } returns mockSendView
         coEvery {
             vaultRepository.createSend(sendView = mockSendView, fileUri = null)
-        } returns CreateSendResult.Error
+        } returns CreateSendResult.Error("Fail")
         val viewModel = createViewModel(initialState)
 
         viewModel.stateFlow.test {
@@ -277,7 +277,7 @@ class AddSendViewModelTest : BaseViewModelTest() {
                 initialState.copy(
                     dialogState = AddSendState.DialogState.Error(
                         title = R.string.an_error_has_occurred.asText(),
-                        message = R.string.generic_error_message.asText(),
+                        message = "Fail".asText(),
                     ),
                 ),
                 awaitItem(),