diff --git a/bootstrapping-lambda/local/index.ts b/bootstrapping-lambda/local/index.ts
index 7b69706a..444fb06d 100644
--- a/bootstrapping-lambda/local/index.ts
+++ b/bootstrapping-lambda/local/index.ts
@@ -1,31 +1,5 @@
-import { AppSync } from "@aws-sdk/client-appsync";
-import {
-  pinboardConfigPromiseGetter,
-  STAGE,
-  standardAwsConfig,
-} from "../../shared/awsIntegration";
-import { APP } from "../../shared/constants";
-import { ENVIRONMENT_VARIABLE_KEYS } from "../../shared/environmentVariables";
+import { initEnvVars } from "./initLocalEnvVars";
 
-pinboardConfigPromiseGetter("sentryDSN").then(
-  (sentryDSN) => (process.env[ENVIRONMENT_VARIABLE_KEYS.sentryDSN] = sentryDSN)
-);
-
-new AppSync(standardAwsConfig)
-  .listGraphqlApis({
-    maxResults: 25, // TODO consider implementing paging (for absolute future proofing)
-  })
-  .then((_) =>
-    _.graphqlApis?.find(
-      (api) => api.tags?.["Stage"] === STAGE && api.tags?.["App"] === APP
-    )
-  )
-  .then((appSyncAPI) => {
-    if (!appSyncAPI) {
-      throw Error("could not find AppSync API");
-    }
-    process.env[ENVIRONMENT_VARIABLE_KEYS.graphqlEndpoint] =
-      appSyncAPI.uris?.["GRAPHQL"];
-
-    import("../src/server"); // actually start the server, once the environment variable is set
-  });
+initEnvVars().then(() => {
+  import("../src/server"); // actually start the server, once the environment variables are set
+});
diff --git a/bootstrapping-lambda/local/initLocalEnvVars.ts b/bootstrapping-lambda/local/initLocalEnvVars.ts
new file mode 100644
index 00000000..c0d5f54f
--- /dev/null
+++ b/bootstrapping-lambda/local/initLocalEnvVars.ts
@@ -0,0 +1,32 @@
+import { AppSync } from "@aws-sdk/client-appsync";
+import {
+  pinboardConfigPromiseGetter,
+  STAGE,
+  standardAwsConfig,
+} from "shared/awsIntegration";
+import { APP } from "shared/constants";
+import { ENVIRONMENT_VARIABLE_KEYS } from "shared/environmentVariables";
+
+export const initEnvVars = (): Promise<void> => {
+  pinboardConfigPromiseGetter("sentryDSN").then(
+    (sentryDSN) =>
+      (process.env[ENVIRONMENT_VARIABLE_KEYS.sentryDSN] = sentryDSN)
+  );
+
+  return new AppSync(standardAwsConfig)
+    .listGraphqlApis({
+      maxResults: 25, // TODO consider implementing paging (for absolute future proofing)
+    })
+    .then((_) =>
+      _.graphqlApis?.find(
+        (api) => api.tags?.["Stage"] === STAGE && api.tags?.["App"] === APP
+      )
+    )
+    .then((appSyncAPI) => {
+      if (!appSyncAPI) {
+        throw Error("could not find AppSync API");
+      }
+      process.env[ENVIRONMENT_VARIABLE_KEYS.graphqlEndpoint] =
+        appSyncAPI.uris?.["GRAPHQL"];
+    });
+};
diff --git a/bootstrapping-lambda/local/simulateOctopus.ts b/bootstrapping-lambda/local/simulateOctopus.ts
new file mode 100644
index 00000000..8b53d35b
--- /dev/null
+++ b/bootstrapping-lambda/local/simulateOctopus.ts
@@ -0,0 +1,58 @@
+import prompts from "prompts";
+import { handleImagingCallFromOctopus } from "../src/octopusImagingHandler";
+import { S3 } from "@aws-sdk/client-s3";
+import { standardAwsConfig } from "shared/awsIntegration";
+import { IMAGINE_REQUEST_TYPES } from "shared/octopusImaging";
+import { getYourEmail } from "shared/local/yourEmail";
+import { initEnvVars } from "./initLocalEnvVars";
+
+initEnvVars().then(async () => {
+  const s3 = new S3(standardAwsConfig);
+
+  const newGridId = "TBC"; //TODO get media id of modified image
+
+  // noinspection InfiniteLoopJS
+  while (
+    // eslint-disable-next-line no-constant-condition
+    true
+  ) {
+    const { args } = await prompts(
+      {
+        type: "select",
+        name: "args",
+        message: "Operation?",
+        choices: [
+          {
+            title: "ImagingOrderPickedUp",
+            value: {},
+          },
+          {
+            title: "GeneratePreSignedGridUploadUrl",
+            value: {
+              originalGridId: "223636f8d305a77e60fb2aa4525effbd66a7560d",
+              filename: "Historic_yachts_22.JPG",
+              newGridId,
+              requestType: IMAGINE_REQUEST_TYPES[0],
+            },
+          },
+          {
+            title: "ImagingOrderCompleted",
+            value: {
+              newGridId,
+            },
+          },
+        ],
+      },
+      { onCancel: () => process.exit() }
+    );
+
+    console.log(
+      (await handleImagingCallFromOctopus(s3, {
+        userEmail: await getYourEmail(),
+        workflowId: "65518",
+        pinboardItemId: "3458",
+        ...args,
+      })) || "DONE"
+    );
+  }
+});
diff --git a/bootstrapping-lambda/package.json b/bootstrapping-lambda/package.json
index cf46e73b..908549e1 100644
--- a/bootstrapping-lambda/package.json
+++ b/bootstrapping-lambda/package.json
@@ -9,6 +9,7 @@
     "test": "jest --coverage --forceExit",
     "bundle": "esbuild src/server.ts --bundle --minify --outfile=dist/index.js  --platform=node --external:aws-sdk --external:@aws-sdk",
     "watch": "ts-node-dev --respawn local/index.ts",
+    "simulate-octopus-call": "ts-node-dev --respawn local/simulateOctopus.ts",
     "build": "run-p --print-label type-check bundle"
   },
   "devDependencies": {
diff --git a/bootstrapping-lambda/src/appSyncRequest.ts b/bootstrapping-lambda/src/appSyncRequest.ts
new file mode 100644
index 00000000..0a20e71b
--- /dev/null
+++ b/bootstrapping-lambda/src/appSyncRequest.ts
@@ -0,0 +1,24 @@
+import { CreateItemInput } from "shared/graphql/graphql";
+import { AppSyncConfig } from "shared/appSyncConfig";
+import { itemReturnFields } from "shared/itemReturnFields";
+import fetch from "node-fetch";
+
+export const appSyncCreateItem = (
+  config: AppSyncConfig,
+  input: CreateItemInput
+) =>
+  fetch(config.graphqlEndpoint, {
+    method: "POST",
+    headers: {
+      authorization: config.authToken,
+      "content-type": "application/json",
+    },
+    body: JSON.stringify({
+      operationName: "SendMessage",
+      variables: {
+        input,
+      },
+      // the client listening to the subscription requires various fields to be returned, hence reuse of itemReturnFields
+      query: `mutation SendMessage($input: CreateItemInput!) { createItem(input: $input) { ${itemReturnFields} } }`,
+    }),
+  });
diff --git a/bootstrapping-lambda/src/octopusImagingHandler.ts b/bootstrapping-lambda/src/octopusImagingHandler.ts
new file mode 100644
index 00000000..64b68638
--- /dev/null
+++ b/bootstrapping-lambda/src/octopusImagingHandler.ts
@@ -0,0 +1,79 @@
+import { S3 } from "@aws-sdk/client-s3";
+import { generateAppSyncConfig } from "./generateAppSyncConfig";
+import { generatePreSignedGridUploadUrl } from "shared/grid";
+import { CreateItemInput } from "shared/graphql/graphql";
+import { appSyncCreateItem } from "./appSyncRequest";
+import {
+  IMAGING_COMPLETED_ITEM_TYPE,
+  IMAGING_PICKED_UP_ITEM_TYPE,
+} from "shared/octopusImaging";
+
+interface CommonArgs {
+  /* the email of the user who did the imaging work */
+  userEmail: string; //TODO probably receive the desktop auth token instead (to verify on pinboard side)
+  /* the id of the pinboard itself */
+  workflowId: string;
+  /* the itemId of the original request item in pinboard */
+  pinboardItemId: string;
+}
+
+type ImagingOrderPickedUp = CommonArgs;
+interface GeneratePreSignedGridUploadUrl extends CommonArgs {
+  originalGridId: string;
+  filename: string;
+  /* SHA1 hash of the file content */
+  newGridId: string;
+  /* e.g. cutout, composite, etc */
+  requestType: string;
+}
+interface ImagingOrderCompleted extends CommonArgs {
+  /* SHA1 hash of the file content */
+  newGridId: string;
+}
+
+export type ImagingCallFromOctopus =
+  | ImagingOrderPickedUp
+  | GeneratePreSignedGridUploadUrl
+  | ImagingOrderCompleted;
+
+export const isImagingCallFromOctopus = (
+  detail: any
+): detail is ImagingCallFromOctopus => !!detail && "pinboardItemId" in detail;
+
+export const handleImagingCallFromOctopus = async (
+  s3: S3,
+  detail: ImagingCallFromOctopus
+): Promise<string | void> => {
+  console.log("Handling imaging call from Octopus", detail);
+  if ("originalGridId" in detail) {
+    return await generatePreSignedGridUploadUrl(detail);
+  }
+  const appSyncConfig = await generateAppSyncConfig(detail.userEmail, s3);
+  const appSyncCreateItemInput: CreateItemInput = {
+    pinboardId: detail.workflowId,
+    relatedItemId: detail.pinboardItemId,
+    claimable: false,
+    mentions: null, //TODO consider @ing the original requester for these updates
+    message: null,
+    groupMentions: null,
+    ...("newGridId" in detail
+      ? {
+          type: IMAGING_COMPLETED_ITEM_TYPE,
+          payload: null, //TODO make use of the newGridId
+        }
+      : {
+          type: IMAGING_PICKED_UP_ITEM_TYPE,
+          payload: null,
+        }),
+  };
+  return appSyncCreateItem(appSyncConfig, appSyncCreateItemInput).then(
+    async (response) => {
+      console.log(await response.text());
+      if (!response.ok) {
+        throw new Error(
+          `Failed to create item: ${response.status} ${response.statusText}`
+        );
+      }
+    }
+  );
+};
diff --git a/bootstrapping-lambda/src/server.ts b/bootstrapping-lambda/src/server.ts
index 45311225..786b46ba 100644
--- a/bootstrapping-lambda/src/server.ts
+++ b/bootstrapping-lambda/src/server.ts
@@ -25,6 +25,11 @@ import {
 } from "./middleware/auth-middleware";
 
 import { getMetrics } from "./reporting/reportingServiceClient";
+import {
+  handleImagingCallFromOctopus,
+  ImagingCallFromOctopus,
+  isImagingCallFromOctopus,
+} from "./octopusImagingHandler";
 
 const s3 = new S3(standardAwsConfig);
 
@@ -162,8 +167,17 @@ if (IS_RUNNING_LOCALLY) {
   const PORT = 3030;
   server.listen(PORT, () => console.log(`Listening on port ${PORT}`));
 } else {
-  exports.handler = (
-    event: lambda.APIGatewayProxyEvent,
+  exports.handler = async (
+    payload: lambda.APIGatewayProxyEvent | ImagingCallFromOctopus,
     context: lambda.Context
-  ) => proxy(createServer(server), event, context);
+  ) => {
+    if ("httpMethod" in payload) {
+      // from API Gateway
+      return proxy(createServer(server), payload, context);
+    } else if (isImagingCallFromOctopus(payload)) {
+      return await handleImagingCallFromOctopus(s3, payload);
+    }
+    console.error("unexpected payload", payload);
+    throw new Error("Not implemented");
+  };
 }
diff --git a/cdk/lib/__snapshots__/stack.test.ts.snap b/cdk/lib/__snapshots__/stack.test.ts.snap
index b1a740cf..29c155ac 100644
--- a/cdk/lib/__snapshots__/stack.test.ts.snap
+++ b/cdk/lib/__snapshots__/stack.test.ts.snap
@@ -29,6 +29,15 @@ Object {
     "gu:cdk:version": "49.5.0",
   },
   "Outputs": Object {
+    "BootstrappingLambdaFunctionName": Object {
+      "Description": "pinboard-bootstrapping-lambda-TEST function name",
+      "Export": Object {
+        "Name": "pinboard-bootstrapping-lambda-TEST-function-name",
+      },
+      "Value": Object {
+        "Ref": "pinboardbootstrappinglambdaD2C487DA",
+      },
+    },
     "pinboardbootstrappinglambdaapiEndpoint4DE1E032": Object {
       "Value": Object {
         "Fn::Join": Array [
diff --git a/cdk/lib/stack.ts b/cdk/lib/stack.ts
index 6bf7823b..0f00e618 100644
--- a/cdk/lib/stack.ts
+++ b/cdk/lib/stack.ts
@@ -644,6 +644,7 @@ export class PinBoardStack extends GuStack {
 
     const bootstrappingLambdaBasename = "pinboard-bootstrapping-lambda";
     const bootstrappingLambdaApiBaseName = `${bootstrappingLambdaBasename}-api`;
+    const bootstrappingLambdaFunctionName = `${bootstrappingLambdaBasename}-${this.stage}`;
 
     const bootstrappingLambdaFunction = new lambda.Function(
       this,
@@ -665,7 +666,7 @@ export class PinBoardStack extends GuStack {
               "/pinboard/sentryDSN"
             ),
         },
-        functionName: `${bootstrappingLambdaBasename}-${this.stage}`,
+        functionName: bootstrappingLambdaFunctionName,
         code: lambda.Code.fromBucket(
           deployBucket,
           `${this.stack}/${this.stage}/${bootstrappingLambdaApiBaseName}/${bootstrappingLambdaApiBaseName}.zip`
@@ -740,5 +741,11 @@ export class PinBoardStack extends GuStack {
       description: `${bootstrappingLambdaApiBaseName}-hostname`,
       value: `${bootstrappingApiDomainName.domainNameAliasDomainName}`,
     });
+
+    new CfnOutput(this, `BootstrappingLambdaFunctionName`, {
+      exportName: `${bootstrappingLambdaFunctionName}-function-name`,
+      description: `${bootstrappingLambdaFunctionName} function name`,
+      value: `${bootstrappingLambdaFunction.functionName}`,
+    });
   }
 }
diff --git a/client/gql.ts b/client/gql.ts
index 550a643c..cdf390b5 100644
--- a/client/gql.ts
+++ b/client/gql.ts
@@ -1,4 +1,5 @@
 import { gql } from "@apollo/client";
+import { itemReturnFields } from "shared/itemReturnFields";
 
 const pinboardReturnFields = `
   composerId
@@ -47,29 +48,6 @@ export const gqlGetItemCounts = gql`
   }
 `;
 
-const itemReturnFields = `
-  id
-  type
-  userEmail
-  timestamp
-  pinboardId
-  message
-  payload
-  mentions {
-    label
-    isMe
-  }
-  groupMentions {
-    label
-    isMe
-  }
-  claimedByEmail
-  claimable
-  relatedItemId
-  editHistory
-  deletedAt
-`;
-
 // TODO: consider updating the resolver (cdk/stack.ts) to use a Query with a secondary index (if performance degrades when we have lots of items)
 export const gqlGetInitialItems = (pinboardId: string) => gql`
     query MyQuery {
diff --git a/client/src/itemDisplay.tsx b/client/src/itemDisplay.tsx
index 71fbc71a..bc5f851c 100644
--- a/client/src/itemDisplay.tsx
+++ b/client/src/itemDisplay.tsx
@@ -24,7 +24,11 @@ import Pencil from "../icons/pencil.svg";
 import { ITEM_HOVER_MENU_CLASS_NAME, ItemHoverMenu } from "./itemHoverMenu";
 import { EditItem } from "./editItem";
 import { Reply } from "./reply";
-import { IMAGING_REQUEST_ITEM_TYPE } from "shared/octopusImaging";
+import {
+  IMAGING_COMPLETED_ITEM_TYPE,
+  IMAGING_PICKED_UP_ITEM_TYPE,
+  IMAGING_REQUEST_ITEM_TYPE,
+} from "shared/octopusImaging";
 
 interface ItemDisplayProps {
   item: Item | PendingItem;
@@ -97,6 +101,8 @@ export const ItemDisplay = ({
     item.userEmail === userEmail &&
     item.type !== "claim" &&
     item.type !== IMAGING_REQUEST_ITEM_TYPE &&
+    item.type !== IMAGING_PICKED_UP_ITEM_TYPE &&
+    item.type !== IMAGING_COMPLETED_ITEM_TYPE &&
     !item.claimedByEmail;
 
   return (
diff --git a/grid-bridge-lambda/src/index.ts b/grid-bridge-lambda/src/index.ts
index 70d33473..a75564f4 100644
--- a/grid-bridge-lambda/src/index.ts
+++ b/grid-bridge-lambda/src/index.ts
@@ -1,20 +1,14 @@
-import fetch from "node-fetch";
-import {
-  pinboardSecretPromiseGetter,
-  STAGE,
-} from "../../shared/awsIntegration";
 import type {
   GridSearchQueryBreakdown,
   GridSearchSummary,
-} from "../../shared/graphql/graphql";
+} from "shared/graphql/graphql";
 
 import { isCollectionResponse, isSearchResponse } from "./types";
 import { PayloadAndType } from "client/src/types/PayloadAndType";
+import { gridFetch, gridTopLevelDomain } from "shared/grid";
 
-const gutoolsDomain =
-  STAGE === "PROD" ? "gutools.co.uk" : "test.dev-gutools.co.uk";
-const mediaApiDomain = `api.media.${gutoolsDomain}`;
-const collectionsDomain = `media-collections.${gutoolsDomain}`;
+const mediaApiHost = `api.media.${gridTopLevelDomain}`;
+const collectionsHost = `media-collections.${gridTopLevelDomain}`;
 const maxImagesInSummary = "4";
 
 export const handler = async (event: {
@@ -28,20 +22,8 @@ export const handler = async (event: {
   }
 };
 
-const gridFetch = async (url: string): Promise<unknown> => {
-  const response = await fetch(url, {
-    headers: {
-      "X-Gu-Media-Key": await pinboardSecretPromiseGetter(
-        `grid/${STAGE === "PROD" ? "PROD" : "CODE"}/apiKey`
-      ),
-    },
-  });
-
-  return await response.json();
-};
-
 const getSearchSummary = async (url: URL): Promise<GridSearchSummary> => {
-  if (url.hostname !== mediaApiDomain || url.pathname !== "/images") {
+  if (url.hostname !== mediaApiHost || url.pathname !== "/images") {
     throw new Error("Invalid Grid search API URL");
   }
   url.searchParams.set("length", maxImagesInSummary);
@@ -87,7 +69,7 @@ async function breakdownQuery(
     [...q.matchAll(COLLECTIONS)].map(async (match) => {
       const text = match[1] ?? match[2] ?? match[3];
       const collectionResponse = await gridFetch(
-        `https://${collectionsDomain}/collections/${text}`
+        `https://${collectionsHost}/collections/${text}`
       );
 
       if (!isCollectionResponse(collectionResponse)) {
@@ -127,7 +109,7 @@ async function breakdownQuery(
 async function buildPayloadFor(gridUrl: URL): Promise<PayloadAndType | null> {
   if (gridUrl.pathname === "/search") {
     const apiUrl = new URL(gridUrl.href);
-    apiUrl.hostname = mediaApiDomain;
+    apiUrl.hostname = mediaApiHost;
     apiUrl.pathname = apiUrl.pathname.replace("/search", "/images");
     apiUrl.searchParams.set("countAll", "true");
     apiUrl.searchParams.set("length", "0");
@@ -150,7 +132,7 @@ async function buildPayloadFor(gridUrl: URL): Promise<PayloadAndType | null> {
   if (gridUrl.pathname.startsWith("/images/")) {
     const maybeCrop = gridUrl.searchParams.get("crop");
     const apiUrl = new URL(gridUrl.href);
-    apiUrl.hostname = mediaApiDomain;
+    apiUrl.hostname = mediaApiHost;
     const imageResponse = (await gridFetch(apiUrl.href)) as {
       data: {
         thumbnail: { secureUrl: string };
diff --git a/shared/graphql/schema.graphql b/shared/graphql/schema.graphql
index cb1d8029..1989d872 100644
--- a/shared/graphql/schema.graphql
+++ b/shared/graphql/schema.graphql
@@ -144,7 +144,7 @@ input CreateItemInput {
   pinboardId: String!
   mentions: [String!]
   groupMentions: [String!]
-  claimable: Boolean
+  claimable: Boolean!
   relatedItemId: String
 }
 
diff --git a/shared/grid.ts b/shared/grid.ts
new file mode 100644
index 00000000..53ebf006
--- /dev/null
+++ b/shared/grid.ts
@@ -0,0 +1,55 @@
+import { pinboardSecretPromiseGetter, STAGE } from "./awsIntegration";
+import fetch from "node-fetch";
+
+export const gridTopLevelDomain =
+  STAGE === "PROD" ? "gutools.co.uk" : "test.dev-gutools.co.uk";
+
+const loaderHost = `loader.media.${gridTopLevelDomain}`;
+
+export const gridFetch = async <BODY extends Record<string, unknown>>(
+  url: string,
+  postBody?: BODY
+): Promise<Record<string, unknown>> => {
+  console.log(postBody);
+  const response = await fetch(url, {
+    method: postBody ? "POST" : "GET",
+    headers: {
+      "X-Gu-Media-Key": await pinboardSecretPromiseGetter(
+        `grid/${STAGE === "PROD" ? "PROD" : "CODE"}/apiKey`
+      ),
+      ...(postBody && { "Content-Type": "application/json" }),
+    },
+    body: postBody && JSON.stringify(postBody),
+  });
+
+  if (response.ok) {
+    // TODO perhaps also check the content type
+    return await response.json();
+  }
+  throw new Error(
+    `Failed to fetch ${url}: ${response.status} ${response.statusText}`
+  );
+};
+
+interface GeneratePreSignedGridUploadUrlArgs {
+  newGridId: string;
+  filename: string;
+  originalGridId: string;
+  /* the email of the user who did the imaging work, who we'll use for on onBehalfOf*/
+  userEmail: string;
+}
+export const generatePreSignedGridUploadUrl = async ({
+  newGridId,
+  filename,
+  originalGridId,
+  userEmail,
+}: GeneratePreSignedGridUploadUrlArgs): Promise<string> => {
+  const requestBody = {
+    [newGridId]: filename,
+  };
+  const response = await gridFetch(
+    `https://${loaderHost}/prepare?originalMediaId=${originalGridId}&onBehalfOf=${userEmail}`,
+    requestBody
+  );
+  return response[newGridId] as string;
+};
diff --git a/shared/itemReturnFields.ts b/shared/itemReturnFields.ts
new file mode 100644
index 00000000..14b1ac42
--- /dev/null
+++ b/shared/itemReturnFields.ts
@@ -0,0 +1,22 @@
+export const itemReturnFields = `
+  id
+  type
+  userEmail
+  timestamp
+  pinboardId
+  message
+  payload
+  mentions {
+    label
+    isMe
+  }
+  groupMentions {
+    label
+    isMe
+  }
+  claimedByEmail
+  claimable
+  relatedItemId
+  editHistory
+  deletedAt
+`;
diff --git a/shared/octopusImaging.ts b/shared/octopusImaging.ts
index 7c1e5d70..df7cbd40 100644
--- a/shared/octopusImaging.ts
+++ b/shared/octopusImaging.ts
@@ -1,4 +1,6 @@
 export const IMAGING_REQUEST_ITEM_TYPE = "imaging-request";
+export const IMAGING_PICKED_UP_ITEM_TYPE = "imaging-picked-up";
+export const IMAGING_COMPLETED_ITEM_TYPE = "imaging-completed";
 
 export const IMAGINE_REQUEST_TYPES = [
   "Cut out", // only 'cut out' is required for now