diff --git a/packages/automerge-repo-network-websocket/src/NodeWSServerAdapter.ts b/packages/automerge-repo-network-websocket/src/NodeWSServerAdapter.ts
index 49c876585..cf92326f4 100644
--- a/packages/automerge-repo-network-websocket/src/NodeWSServerAdapter.ts
+++ b/packages/automerge-repo-network-websocket/src/NodeWSServerAdapter.ts
@@ -123,6 +123,14 @@ export class NodeWSServerAdapter extends NetworkAdapter {
     )
     switch (type) {
       case "join":
+        const existingSocket = this.sockets[senderId]
+        if (existingSocket) {
+          if (existingSocket.readyState === WebSocket.OPEN) {
+            existingSocket.close()
+          }
+          this.emit("peer-disconnected", {peerId: senderId})
+        }
+
         // Let the rest of the system know that we have a new connection.
         this.emit("peer-candidate", { peerId: senderId })
         this.sockets[senderId] = socket
diff --git a/packages/automerge-repo-network-websocket/test/Websocket.test.ts b/packages/automerge-repo-network-websocket/test/Websocket.test.ts
index 9153a480c..1c68ea374 100644
--- a/packages/automerge-repo-network-websocket/test/Websocket.test.ts
+++ b/packages/automerge-repo-network-websocket/test/Websocket.test.ts
@@ -1,4 +1,5 @@
-import { PeerId, Repo } from "@automerge/automerge-repo"
+import { next as A } from "@automerge/automerge"
+import { AutomergeUrl, DocumentId, PeerId, Repo, SyncMessage, parseAutomergeUrl } from "@automerge/automerge-repo"
 import assert from "assert"
 import * as CBOR from "cbor-x"
 import { once } from "events"
@@ -6,8 +7,10 @@ import http from "http"
 import { describe, it } from "vitest"
 import WebSocket, { AddressInfo } from "ws"
 import { runAdapterTests } from "../../automerge-repo/src/helpers/tests/network-adapter-tests.js"
+import { DummyStorageAdapter } from "../../automerge-repo/test/helpers/DummyStorageAdapter.js"
 import { BrowserWebSocketClientAdapter } from "../src/BrowserWebSocketClientAdapter.js"
 import { NodeWSServerAdapter } from "../src/NodeWSServerAdapter.js"
+import {headsAreSame} from "@automerge/automerge-repo/src/helpers/headsAreSame.js"
 
 describe("Websocket adapters", () => {
   const setup = async (clientCount = 1) => {
@@ -152,6 +155,18 @@ describe("Websocket adapters", () => {
       return message
     }
 
+    async function recvOrTimeout(socket: WebSocket): Promise<Buffer | null> {
+      return new Promise((resolve) => {
+        const timer = setTimeout(() => {
+          resolve(null)
+        }, 1000)
+        socket.once("message", (msg) => {
+          clearTimeout(timer)
+          resolve(msg as Buffer)
+        })
+      })
+    }
+
     it("should send the negotiated protocol version in its hello message", async () => {
       const response = await serverResponse({
         type: "join",
@@ -192,6 +207,185 @@ describe("Websocket adapters", () => {
         selectedProtocolVersion: "1",
       })
     })
+
+    /** 
+     *  Create a new document, initialized with the given contents and return a
+     *  storage containign that document as well as the URL and a fork of the
+     *  document
+     *
+     *  @param contents - The contents to initialize the document with
+     */
+    async function initDocAndStorage<T extends Record<string, unknown>>(contents: T): Promise<{
+          storage: DummyStorageAdapter,
+          url: AutomergeUrl,
+          doc: A.Doc<T>,
+          documentId: DocumentId
+        }> {
+      const storage = new DummyStorageAdapter()
+      const silentRepo = new Repo({storage, network: []})
+      const doc = A.from<T>(contents)
+      const handle = silentRepo.create()
+      handle.update(() => A.clone(doc))
+      const { documentId } = parseAutomergeUrl(handle.url)
+      await pause(150)
+      return {
+        url: handle.url,
+        doc,
+        documentId,
+        storage,
+      }
+    }
+
+    function assertIsPeerMessage(msg: Buffer | null) {
+      if (msg == null) {
+        throw new Error("expected a peer message, got null")
+      }
+      let decoded = CBOR.decode(msg)
+      if (decoded.type !== "peer") {
+        throw new Error(`expected a peer message, got type: ${decoded.type}`)
+      }
+    }
+
+    function assertIsSyncMessage(forDocument: DocumentId, msg: Buffer | null): SyncMessage {
+      if (msg == null) {
+        throw new Error("expected a peer message, got null")
+      }
+      let decoded = CBOR.decode(msg)
+      if (decoded.type !== "sync") {
+        throw new Error(`expected a peer message, got type: ${decoded.type}`)
+      }
+      if (decoded.documentId !== forDocument) {
+        throw new Error(`expected a sync message for ${forDocument}, not for ${decoded.documentId}`)
+      }
+      return decoded
+    }
+
+    it("should disconnect existing peers on reconnect before announcing them", async () => {
+      // This test exercises a sync loop which is exposed in the following 
+      // sequence of events:
+      //
+      // 1. A document exists on both the server and the client with divergent
+      //    heads (both sides have changes the other does not have)
+      // 2. The client sends a sync message to the server
+      // 3. The server responds, but for some reason the server response is
+      //    dropped
+      // 4. The client reconnects due to not receiving a response or a ping
+      // 5. The peers exchange sync messages, but the server thinks it has
+      //    already sent its changes to the client, so it doesn't sent them.
+      // 6. The client notices that it doesn't have the servers changes so it
+      //    asks for them
+      // 7. The server responds with an empty sync message because it thinks it
+      //    has already sent the changes
+      // 
+      // 6 and 7 continue in an infinite loop. The root cause is the servers
+      // failure to clear the sync state associated with the given peer when
+      // it receives a new connection from the same peer ID.
+      const { socket, serverUrl } = await setup(0)
+
+      // Create a doc, populate a DummyStorageAdapter with that doc
+      const {storage, url, doc, documentId} = await initDocAndStorage({foo: "bar"})
+
+      // Create a copy of the document to represent the client state
+      let clientDoc = A.clone<{foo: string}>(doc)
+      clientDoc = A.change(clientDoc, d => d.foo = "qux")
+
+      // Now create a websocket sync server with the original document in it's storage
+      const adapter = new NodeWSServerAdapter(socket)
+      const repo = new Repo({ network: [adapter], storage, peerId: "server" as PeerId })
+
+      // make a change to the handle on the sync server
+      const handle = repo.find<{foo: string}>(url)
+      await handle.whenReady()
+      handle.change(d => d.foo = "baz")
+
+      // Okay, so now there is a document on both the client and the server
+      // which has concurrent changes on each peer.
+
+      // Simulate the initial websocket connection
+      let clientSocket = new WebSocket(serverUrl)
+      await once(clientSocket, "open")
+
+      // Run through the client/server hello
+      clientSocket.send(CBOR.encode({
+        type: "join",
+        senderId: "client",
+        supportedProtocolVersions: ["1"],
+      }))
+
+      let response = await recvOrTimeout(clientSocket)
+      assertIsPeerMessage(response)
+
+      // Okay now we start syncing
+
+      let clientState = A.initSyncState()
+      let [newSyncState, message] = A.generateSyncMessage(clientDoc, clientState)
+      clientState = newSyncState
+
+      // Send the initial sync state
+      clientSocket.send(CBOR.encode({
+        type: "request",
+        documentId,
+        targetId: "server",
+        senderId: "client",
+        data: message
+      }))
+
+      response = await recvOrTimeout(clientSocket)
+      assertIsSyncMessage(documentId, response)
+
+      // Now, assume either the network or the server is going slow, so the 
+      // server thinks it has sent the response above, but for whatever reason
+      // it never gets to the client. In that case the reconnect timer in the 
+      // BrowserWebSocketClientAdapter will fire and we'll create a new
+      // websocket and connect it. To simulate this we drop the above response
+      // on the floor and start connecting again.
+
+      clientSocket = new WebSocket(serverUrl)
+      await once(clientSocket, "open")
+
+      // and we also make a change to the client doc
+      clientDoc = A.change(clientDoc, d => d.foo = "quoxen")
+
+      // Run through the whole client/server hello dance again
+      clientSocket.send(CBOR.encode({
+        type: "join",
+        senderId: "client",
+        supportedProtocolVersions: ["1"],
+      }))
+
+      response = await recvOrTimeout(clientSocket)
+      assertIsPeerMessage(response)
+
+      // Now, we start syncing. If we're not buggy, this loop should terminate.
+      while(true) {
+        ;[clientState, message] = A.generateSyncMessage(clientDoc, clientState)
+        if (message) {
+          clientSocket.send(CBOR.encode({
+            type: "sync",
+            documentId,
+            targetId: "server",
+            senderId: "client",
+            data: message
+          }))
+        }
+        const response = await recvOrTimeout(clientSocket)
+        if (response) {
+          const decoded = assertIsSyncMessage(documentId, response)
+          ;[clientDoc, clientState] = A.receiveSyncMessage(clientDoc, clientState, decoded.data)
+        }
+        if (response == null && message == null) {
+          break
+        }
+        // Make sure shit has time to happen
+        await pause(50)
+      }
+
+      let localHeads = A.getHeads(clientDoc)
+      let remoteHeads = A.getHeads(handle.docSync())
+      if (!headsAreSame(localHeads, remoteHeads)) {
+        throw new Error("heads not equal")
+      }
+    })
   })
 })