diff --git a/packages/backend-core/src/sql/sql.ts b/packages/backend-core/src/sql/sql.ts
index 72ff8d4578..cdc5f3d3c8 100644
--- a/packages/backend-core/src/sql/sql.ts
+++ b/packages/backend-core/src/sql/sql.ts
@@ -449,8 +449,12 @@ class InternalBuilder {
         query = query.orderBy(`${aliased}.${key}`, direction, nulls)
       }
     }
-    // always add sorting by the primary key - make sure result is deterministic
-    query = query.orderBy(`${aliased}.${primaryKey[0]}`)
+
+    // add sorting by the primary key if the result isn't already sorted by it,
+    // to make sure result is deterministic
+    if (!sort || sort[primaryKey[0]] === undefined) {
+      query = query.orderBy(`${aliased}.${primaryKey[0]}`)
+    }
     return query
   }
 
@@ -604,7 +608,8 @@ class InternalBuilder {
       if (!primary) {
         throw new Error("Primary key is required for upsert")
       }
-      return query.insert(parsedBody).onConflict(primary).merge()
+      const ret = query.insert(parsedBody).onConflict(primary).merge()
+      return ret
     } else if (this.client === SqlClient.MS_SQL) {
       // No upsert or onConflict support in MSSQL yet, see:
       //   https://github.com/knex/knex/pull/6050
diff --git a/packages/builder/src/components/backend/TableNavigator/ExistingTableDataImport.svelte b/packages/builder/src/components/backend/TableNavigator/ExistingTableDataImport.svelte
index de56fa8ce5..80655d1099 100644
--- a/packages/builder/src/components/backend/TableNavigator/ExistingTableDataImport.svelte
+++ b/packages/builder/src/components/backend/TableNavigator/ExistingTableDataImport.svelte
@@ -1,9 +1,14 @@
 <script>
-  import { FieldType, BBReferenceFieldSubType } from "@budibase/types"
+  import {
+    FieldType,
+    BBReferenceFieldSubType,
+    SourceName,
+  } from "@budibase/types"
   import { Select, Toggle, Multiselect } from "@budibase/bbui"
   import { DB_TYPE_INTERNAL } from "constants/backend"
   import { API } from "api"
   import { parseFile } from "./utils"
+  import { tables, datasources } from "stores/builder"
 
   let error = null
   let fileName = null
@@ -80,6 +85,9 @@
     schema = fetchSchema(tableId)
   }
 
+  $: table = $tables.list.find(table => table._id === tableId)
+  $: datasource = $datasources.list.find(ds => ds._id === table?.sourceId)
+
   async function fetchSchema(tableId) {
     try {
       const definition = await API.fetchTableDefinition(tableId)
@@ -185,20 +193,25 @@
       </div>
     {/each}
   </div>
-  {#if tableType === DB_TYPE_INTERNAL}
-    <br />
+  <br />
+  <!-- SQL Server doesn't yet support overwriting rows by existing keys -->
+  {#if datasource?.source !== SourceName.SQL_SERVER}
     <Toggle
       bind:value={updateExistingRows}
       on:change={() => (identifierFields = [])}
       thin
       text="Update existing rows"
     />
-    {#if updateExistingRows}
+  {/if}
+  {#if updateExistingRows}
+    {#if tableType === DB_TYPE_INTERNAL}
       <Multiselect
         label="Identifier field(s)"
         options={Object.keys(validation)}
         bind:value={identifierFields}
       />
+    {:else}
+      <p>Rows will be updated based on the table's primary key.</p>
     {/if}
   {/if}
   {#if invalidColumns.length > 0}
diff --git a/packages/pro b/packages/pro
index bf30f47a28..6c8d0174ca 160000
--- a/packages/pro
+++ b/packages/pro
@@ -1 +1 @@
-Subproject commit bf30f47a28292d619cf0837f21d66790ff31c3a6
+Subproject commit 6c8d0174ca58c578a37022965ddb923fdbf8e32a
diff --git a/packages/server/scripts/integrations/mssql/data/Dockerfile b/packages/server/scripts/integrations/mssql/data/Dockerfile
index b8c96e8419..c26af556a9 100644
--- a/packages/server/scripts/integrations/mssql/data/Dockerfile
+++ b/packages/server/scripts/integrations/mssql/data/Dockerfile
@@ -1,4 +1,4 @@
-FROM mcr.microsoft.com/mssql/server:2017-latest
+FROM mcr.microsoft.com/mssql/server:2022-latest
 
 ENV ACCEPT_EULA=Y
 ENV SA_PASSWORD=Passw0rd
diff --git a/packages/server/src/api/controllers/row/ExternalRequest.ts b/packages/server/src/api/controllers/row/ExternalRequest.ts
index 1ce8d29e5f..b51de46e99 100644
--- a/packages/server/src/api/controllers/row/ExternalRequest.ts
+++ b/packages/server/src/api/controllers/row/ExternalRequest.ts
@@ -316,7 +316,13 @@ export class ExternalRequest<T extends Operation> {
       manyRelationships: ManyRelationship[] = []
     for (let [key, field] of Object.entries(table.schema)) {
       // if set already, or not set just skip it
-      if (row[key] === undefined || newRow[key] || !isEditableColumn(field)) {
+      if (row[key] === undefined || newRow[key]) {
+        continue
+      }
+      if (
+        !(this.operation === Operation.BULK_UPSERT) &&
+        !isEditableColumn(field)
+      ) {
         continue
       }
       // parse floats/numbers
@@ -690,6 +696,7 @@ export class ExternalRequest<T extends Operation> {
       },
       meta: {
         table,
+        id: config.id,
       },
     }
 
diff --git a/packages/server/src/api/controllers/table/external.ts b/packages/server/src/api/controllers/table/external.ts
index 6ca8cdd82c..c3356919c8 100644
--- a/packages/server/src/api/controllers/table/external.ts
+++ b/packages/server/src/api/controllers/table/external.ts
@@ -16,6 +16,7 @@ import {
 import sdk from "../../../sdk"
 import { builderSocket } from "../../../websockets"
 import { inputProcessing } from "../../../utilities/rowProcessor"
+import { isEqual } from "lodash"
 
 function getDatasourceId(table: Table) {
   if (!table) {
@@ -85,15 +86,30 @@ export async function bulkImport(
   ctx: UserCtx<BulkImportRequest, BulkImportResponse>
 ) {
   let table = await sdk.tables.getTable(ctx.params.tableId)
-  const { rows } = ctx.request.body
+  const { rows, identifierFields } = ctx.request.body
   const schema = table.schema
 
+  if (
+    identifierFields &&
+    identifierFields.length > 0 &&
+    !isEqual(identifierFields, table.primary)
+  ) {
+    // This is becuse we make use of the ON CONFLICT functionality in SQL
+    // databases, which only triggers when there's a conflict against a unique
+    // index. The only unique index we can count on atm in Budibase is the
+    // primary key, so this functionality always uses the primary key.
+    ctx.throw(
+      400,
+      "Identifier fields are not supported for bulk import into an external datasource."
+    )
+  }
+
   if (!rows || !isRows(rows) || !isSchema(schema)) {
     ctx.throw(400, "Provided data import information is invalid.")
   }
 
   const parsedRows = []
-  for (const row of parse(rows, schema)) {
+  for (const row of parse(rows, table)) {
     const processed = await inputProcessing(ctx.user?._id, table, row, {
       noAutoRelationships: true,
     })
diff --git a/packages/server/src/api/controllers/table/utils.ts b/packages/server/src/api/controllers/table/utils.ts
index a42cfc43c3..0e9a32b294 100644
--- a/packages/server/src/api/controllers/table/utils.ts
+++ b/packages/server/src/api/controllers/table/utils.ts
@@ -178,7 +178,7 @@ export async function handleDataImport(
   }
 
   const db = context.getAppDB()
-  const data = parse(importRows, schema)
+  const data = parse(importRows, table)
 
   let finalData: any = await importToRows(data, table, user)
 
diff --git a/packages/server/src/api/routes/tests/row.spec.ts b/packages/server/src/api/routes/tests/row.spec.ts
index 4d1b4f028b..b6e3edf5ff 100644
--- a/packages/server/src/api/routes/tests/row.spec.ts
+++ b/packages/server/src/api/routes/tests/row.spec.ts
@@ -1,4 +1,8 @@
-import { DatabaseName, getDatasource } from "../../../integrations/tests/utils"
+import {
+  DatabaseName,
+  getDatasource,
+  knexClient,
+} from "../../../integrations/tests/utils"
 
 import tk from "timekeeper"
 import emitter from "../../../../src/events"
@@ -31,6 +35,7 @@ import {
 import { generator, mocks } from "@budibase/backend-core/tests"
 import _, { merge } from "lodash"
 import * as uuid from "uuid"
+import { Knex } from "knex"
 
 const timestamp = new Date("2023-01-26T11:48:57.597Z").toISOString()
 tk.freeze(timestamp)
@@ -70,13 +75,16 @@ describe.each([
 
   let table: Table
   let datasource: Datasource | undefined
+  let client: Knex | undefined
 
   beforeAll(async () => {
     await config.init()
     if (dsProvider) {
+      const rawDatasource = await dsProvider
       datasource = await config.createDatasource({
-        datasource: await dsProvider,
+        datasource: rawDatasource,
       })
+      client = await knexClient(rawDatasource)
     }
   })
 
@@ -307,13 +315,13 @@ describe.each([
         // as quickly as possible.
         await Promise.all(
           sequence.map(async () => {
-            const attempts = 20
+            const attempts = 30
             for (let attempt = 0; attempt < attempts; attempt++) {
               try {
                 await config.api.row.save(table._id!, {})
                 return
               } catch (e) {
-                await new Promise(r => setTimeout(r, Math.random() * 15))
+                await new Promise(r => setTimeout(r, Math.random() * 50))
               }
             }
             throw new Error(`Failed to create row after ${attempts} attempts`)
@@ -598,6 +606,35 @@ describe.each([
       expect(res.name).toEqual("Updated Name")
       await assertRowUsage(rowUsage)
     })
+
+    !isInternal &&
+      it("can update a row on an external table with a primary key", async () => {
+        const tableName = uuid.v4().substring(0, 10)
+        await client!.schema.createTable(tableName, table => {
+          table.increments("id").primary()
+          table.string("name")
+        })
+
+        const res = await config.api.datasource.fetchSchema({
+          datasourceId: datasource!._id!,
+        })
+        const table = res.datasource.entities![tableName]
+
+        const row = await config.api.row.save(table._id!, {
+          id: 1,
+          name: "Row 1",
+        })
+
+        const updatedRow = await config.api.row.save(table._id!, {
+          _id: row._id!,
+          name: "Row 1 Updated",
+        })
+
+        expect(updatedRow.name).toEqual("Row 1 Updated")
+
+        const rows = await config.api.row.fetch(table._id!)
+        expect(rows).toHaveLength(1)
+      })
   })
 
   describe("patch", () => {
@@ -667,6 +704,7 @@ describe.each([
       expect(event.oldRow.description).toEqual(beforeRow.description)
       expect(event.row.description).toEqual(beforeRow.description)
     })
+
     it("should throw an error when given improper types", async () => {
       const existing = await config.api.row.save(table._id!, {})
       const rowUsage = await getRowUsage()
@@ -758,7 +796,8 @@ describe.each([
     })
 
     !isInternal &&
-      // TODO: SQL is having issues creating composite keys
+      // MSSQL needs a setting called IDENTITY_INSERT to be set to ON to allow writing
+      // to identity columns. This is not something Budibase does currently.
       providerType !== DatabaseName.SQL_SERVER &&
       it("should support updating fields that are part of a composite key", async () => {
         const tableRequest = saveTableRequest({
@@ -911,32 +950,21 @@ describe.each([
       await assertRowUsage(isInternal ? rowUsage - 1 : rowUsage)
     })
 
-    it("Should ignore malformed/invalid delete requests", async () => {
-      const rowUsage = await getRowUsage()
+    it.each([{ not: "valid" }, { rows: 123 }, "invalid"])(
+      "Should ignore malformed/invalid delete request: %s",
+      async (request: any) => {
+        const rowUsage = await getRowUsage()
 
-      await config.api.row.delete(table._id!, { not: "valid" } as any, {
-        status: 400,
-        body: {
-          message: "Invalid delete rows request",
-        },
-      })
+        await config.api.row.delete(table._id!, request, {
+          status: 400,
+          body: {
+            message: "Invalid delete rows request",
+          },
+        })
 
-      await config.api.row.delete(table._id!, { rows: 123 } as any, {
-        status: 400,
-        body: {
-          message: "Invalid delete rows request",
-        },
-      })
-
-      await config.api.row.delete(table._id!, "invalid" as any, {
-        status: 400,
-        body: {
-          message: "Invalid delete rows request",
-        },
-      })
-
-      await assertRowUsage(rowUsage)
-    })
+        await assertRowUsage(rowUsage)
+      }
+    )
   })
 
   describe("bulkImport", () => {
@@ -1085,6 +1113,121 @@ describe.each([
         expect(rows[2].name).toEqual("Row 3")
         expect(rows[2].description).toEqual("Row 3 description")
       })
+
+    // Upserting isn't yet supported in MSSQL, see:
+    //   https://github.com/knex/knex/pull/6050
+    !isMSSQL &&
+      !isInternal &&
+      it("should be able to update existing rows with composite primary keys with bulkImport", async () => {
+        const tableName = uuid.v4()
+        await client?.schema.createTable(tableName, table => {
+          table.integer("companyId")
+          table.integer("userId")
+          table.string("name")
+          table.string("description")
+          table.primary(["companyId", "userId"])
+        })
+
+        const resp = await config.api.datasource.fetchSchema({
+          datasourceId: datasource!._id!,
+        })
+        const table = resp.datasource.entities![tableName]
+
+        const row1 = await config.api.row.save(table._id!, {
+          companyId: 1,
+          userId: 1,
+          name: "Row 1",
+          description: "Row 1 description",
+        })
+
+        const row2 = await config.api.row.save(table._id!, {
+          companyId: 1,
+          userId: 2,
+          name: "Row 2",
+          description: "Row 2 description",
+        })
+
+        await config.api.row.bulkImport(table._id!, {
+          identifierFields: ["companyId", "userId"],
+          rows: [
+            {
+              companyId: 1,
+              userId: row1.userId,
+              name: "Row 1 updated",
+              description: "Row 1 description updated",
+            },
+            {
+              companyId: 1,
+              userId: row2.userId,
+              name: "Row 2 updated",
+              description: "Row 2 description updated",
+            },
+            {
+              companyId: 1,
+              userId: 3,
+              name: "Row 3",
+              description: "Row 3 description",
+            },
+          ],
+        })
+
+        const rows = await config.api.row.fetch(table._id!)
+        expect(rows.length).toEqual(3)
+
+        rows.sort((a, b) => a.name.localeCompare(b.name))
+        expect(rows[0].name).toEqual("Row 1 updated")
+        expect(rows[0].description).toEqual("Row 1 description updated")
+        expect(rows[1].name).toEqual("Row 2 updated")
+        expect(rows[1].description).toEqual("Row 2 description updated")
+        expect(rows[2].name).toEqual("Row 3")
+        expect(rows[2].description).toEqual("Row 3 description")
+      })
+
+    // Upserting isn't yet supported in MSSQL, see:
+    //   https://github.com/knex/knex/pull/6050
+    !isMSSQL &&
+      !isInternal &&
+      it("should be able to update existing rows an autoID primary key", async () => {
+        const tableName = uuid.v4()
+        await client!.schema.createTable(tableName, table => {
+          table.increments("userId").primary()
+          table.string("name")
+        })
+
+        const resp = await config.api.datasource.fetchSchema({
+          datasourceId: datasource!._id!,
+        })
+        const table = resp.datasource.entities![tableName]
+
+        const row1 = await config.api.row.save(table._id!, {
+          name: "Clare",
+        })
+
+        const row2 = await config.api.row.save(table._id!, {
+          name: "Jeff",
+        })
+
+        await config.api.row.bulkImport(table._id!, {
+          identifierFields: ["userId"],
+          rows: [
+            {
+              userId: row1.userId,
+              name: "Clare updated",
+            },
+            {
+              userId: row2.userId,
+              name: "Jeff updated",
+            },
+          ],
+        })
+
+        const rows = await config.api.row.fetch(table._id!)
+        expect(rows.length).toEqual(2)
+
+        rows.sort((a, b) => a.name.localeCompare(b.name))
+        expect(rows[0].name).toEqual("Clare updated")
+        expect(rows[1].name).toEqual("Jeff updated")
+      })
   })
 
   describe("enrich", () => {
diff --git a/packages/server/src/api/routes/tests/search.spec.ts b/packages/server/src/api/routes/tests/search.spec.ts
index 23c2ca819c..589f129f31 100644
--- a/packages/server/src/api/routes/tests/search.spec.ts
+++ b/packages/server/src/api/routes/tests/search.spec.ts
@@ -1,5 +1,9 @@
 import { tableForDatasource } from "../../../tests/utilities/structures"
-import { DatabaseName, getDatasource } from "../../../integrations/tests/utils"
+import {
+  DatabaseName,
+  getDatasource,
+  knexClient,
+} from "../../../integrations/tests/utils"
 import { db as dbCore, utils } from "@budibase/backend-core"
 
 import * as setup from "./utilities"
@@ -24,6 +28,8 @@ import _ from "lodash"
 import tk from "timekeeper"
 import { encodeJSBinding } from "@budibase/string-templates"
 import { dataFilters } from "@budibase/shared-core"
+import { Knex } from "knex"
+import { structures } from "@budibase/backend-core/tests"
 
 describe.each([
   ["in-memory", undefined],
@@ -42,6 +48,7 @@ describe.each([
 
   let envCleanup: (() => void) | undefined
   let datasource: Datasource | undefined
+  let client: Knex | undefined
   let table: Table
   let rows: Row[]
 
@@ -63,8 +70,10 @@ describe.each([
     }
 
     if (dsProvider) {
+      const rawDatasource = await dsProvider
+      client = await knexClient(rawDatasource)
       datasource = await config.createDatasource({
-        datasource: await dsProvider,
+        datasource: rawDatasource,
       })
     }
   })
@@ -909,6 +918,44 @@ describe.each([
           }).toMatchExactly([{ name: "foo" }, { name: "bar" }])
         })
       })
+
+      !isInternal &&
+        !isInMemory &&
+        // This test was added because we automatically add in a sort by the
+        // primary key, and we used to do this unconditionally which caused
+        // problems because it was possible for the primary key to appear twice
+        // in the resulting SQL ORDER BY clause, resulting in an SQL error.
+        // We now check first to make sure that the primary key isn't already
+        // in the sort before adding it.
+        describe("sort on primary key", () => {
+          beforeAll(async () => {
+            const tableName = structures.uuid().substring(0, 10)
+            await client!.schema.createTable(tableName, t => {
+              t.string("name").primary()
+            })
+            const resp = await config.api.datasource.fetchSchema({
+              datasourceId: datasource!._id!,
+            })
+
+            table = resp.datasource.entities![tableName]
+
+            await createRows([{ name: "foo" }, { name: "bar" }])
+          })
+
+          it("should be able to sort by a primary key column ascending", async () =>
+            expectSearch({
+              query: {},
+              sort: "name",
+              sortOrder: SortOrder.ASCENDING,
+            }).toMatchExactly([{ name: "bar" }, { name: "foo" }]))
+
+          it("should be able to sort by a primary key column descending", async () =>
+            expectSearch({
+              query: {},
+              sort: "name",
+              sortOrder: SortOrder.DESCENDING,
+            }).toMatchExactly([{ name: "foo" }, { name: "bar" }]))
+        })
     })
   })
 
diff --git a/packages/server/src/utilities/schema.ts b/packages/server/src/utilities/schema.ts
index 8e6cd34c7c..e473675633 100644
--- a/packages/server/src/utilities/schema.ts
+++ b/packages/server/src/utilities/schema.ts
@@ -4,6 +4,7 @@ import {
   TableSchema,
   FieldSchema,
   Row,
+  Table,
 } from "@budibase/types"
 import { ValidColumnNameRegex, helpers, utils } from "@budibase/shared-core"
 import { db } from "@budibase/backend-core"
@@ -118,16 +119,26 @@ export function validate(rows: Rows, schema: TableSchema): ValidationResults {
   return results
 }
 
-export function parse(rows: Rows, schema: TableSchema): Rows {
+export function parse(rows: Rows, table: Table): Rows {
   return rows.map(row => {
     const parsedRow: Row = {}
 
     Object.entries(row).forEach(([columnName, columnData]) => {
-      if (!(columnName in schema) || schema[columnName]?.autocolumn) {
+      const schema = table.schema
+      if (!(columnName in schema)) {
         // Objects can be present in the row data but not in the schema, so make sure we don't proceed in such a case
         return
       }
 
+      if (
+        schema[columnName].autocolumn &&
+        !table.primary?.includes(columnName)
+      ) {
+        // Don't want the user specifying values for autocolumns unless they're updating
+        // a row through its primary key.
+        return
+      }
+
       const columnSchema = schema[columnName]
       const { type: columnType } = columnSchema
       if (columnType === FieldType.NUMBER) {