diff --git a/coderd/apidoc/docs.go b/coderd/apidoc/docs.go
index f130d8b606..b39237432e 100644
--- a/coderd/apidoc/docs.go
+++ b/coderd/apidoc/docs.go
@@ -4599,6 +4599,12 @@ const docTemplate = `{
                         "description": "Follow log stream",
                         "name": "follow",
                         "in": "query"
+                    },
+                    {
+                        "type": "boolean",
+                        "description": "Disable compression for WebSocket connection",
+                        "name": "no_compression",
+                        "in": "query"
                     }
                 ],
                 "responses": {
diff --git a/coderd/apidoc/swagger.json b/coderd/apidoc/swagger.json
index 4049028734..2449c7fbb9 100644
--- a/coderd/apidoc/swagger.json
+++ b/coderd/apidoc/swagger.json
@@ -4049,6 +4049,12 @@
             "description": "Follow log stream",
             "name": "follow",
             "in": "query"
+          },
+          {
+            "type": "boolean",
+            "description": "Disable compression for WebSocket connection",
+            "name": "no_compression",
+            "in": "query"
           }
         ],
         "responses": {
diff --git a/coderd/workspaceagents.go b/coderd/workspaceagents.go
index 9a5453192c..2c8d894868 100644
--- a/coderd/workspaceagents.go
+++ b/coderd/workspaceagents.go
@@ -405,6 +405,7 @@ func (api *API) patchWorkspaceAgentStartupLogs(rw http.ResponseWriter, r *http.R
 // @Param before query int false "Before log id"
 // @Param after query int false "After log id"
 // @Param follow query bool false "Follow log stream"
+// @Param no_compression query bool false "Disable compression for WebSocket connection"
 // @Success 200 {array} codersdk.WorkspaceAgentStartupLog
 // @Router /workspaceagents/{workspaceagent}/startup-logs [get]
 func (api *API) workspaceAgentStartupLogs(rw http.ResponseWriter, r *http.Request) {
@@ -415,6 +416,7 @@ func (api *API) workspaceAgentStartupLogs(rw http.ResponseWriter, r *http.Reques
 		logger         = api.Logger.With(slog.F("workspace_agent_id", workspaceAgent.ID))
 		follow         = r.URL.Query().Has("follow")
 		afterRaw       = r.URL.Query().Get("after")
+		noCompression  = r.URL.Query().Has("no_compression")
 	)
 
 	var after int64
@@ -460,7 +462,21 @@ func (api *API) workspaceAgentStartupLogs(rw http.ResponseWriter, r *http.Reques
 	api.WebsocketWaitGroup.Add(1)
 	api.WebsocketWaitMutex.Unlock()
 	defer api.WebsocketWaitGroup.Done()
-	conn, err := websocket.Accept(rw, r, nil)
+
+	opts := &websocket.AcceptOptions{}
+
+	// Allow client to request no compression. This is useful for buggy
+	// clients or if there's a client/server incompatibility. This is
+	// needed with e.g. nhooyr/websocket and Safari (confirmed in 16.5).
+	//
+	// See:
+	// * https://github.com/nhooyr/websocket/issues/218
+	// * https://github.com/gobwas/ws/issues/169
+	if noCompression {
+		opts.CompressionMode = websocket.CompressionDisabled
+	}
+
+	conn, err := websocket.Accept(rw, r, opts)
 	if err != nil {
 		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
 			Message: "Failed to accept websocket.",
diff --git a/docs/api/agents.md b/docs/api/agents.md
index e251737826..d1fa59cdff 100644
--- a/docs/api/agents.md
+++ b/docs/api/agents.md
@@ -689,12 +689,13 @@ curl -X GET http://coder-server:8080/api/v2/workspaceagents/{workspaceagent}/sta
 
 ### Parameters
 
-| Name             | In    | Type         | Required | Description        |
-| ---------------- | ----- | ------------ | -------- | ------------------ |
-| `workspaceagent` | path  | string(uuid) | true     | Workspace agent ID |
-| `before`         | query | integer      | false    | Before log id      |
-| `after`          | query | integer      | false    | After log id       |
-| `follow`         | query | boolean      | false    | Follow log stream  |
+| Name             | In    | Type         | Required | Description                                  |
+| ---------------- | ----- | ------------ | -------- | -------------------------------------------- |
+| `workspaceagent` | path  | string(uuid) | true     | Workspace agent ID                           |
+| `before`         | query | integer      | false    | Before log id                                |
+| `after`          | query | integer      | false    | After log id                                 |
+| `follow`         | query | boolean      | false    | Follow log stream                            |
+| `no_compression` | query | boolean      | false    | Disable compression for WebSocket connection |
 
 ### Example responses
 
diff --git a/site/src/api/api.ts b/site/src/api/api.ts
index f9404d0853..9b0af8f942 100644
--- a/site/src/api/api.ts
+++ b/site/src/api/api.ts
@@ -4,6 +4,7 @@ import * as Types from "./types"
 import { DeploymentConfig } from "./types"
 import * as TypesGen from "./typesGenerated"
 import { delay } from "utils/delay"
+import userAgentParser from "ua-parser-js"
 
 // Adds 304 for the default axios validateStatus function
 // https://github.com/axios/axios#handling-errors Check status here
@@ -1231,9 +1232,19 @@ export const watchStartupLogs = (
   agentId: string,
   { after, onMessage, onDone, onError }: WatchStartupLogsOptions,
 ) => {
+  // WebSocket compression in Safari (confirmed in 16.5) is broken when
+  // the server sends large messages. The following error is seen:
+  //
+  //   WebSocket connection to 'wss://.../startup-logs?follow&after=0' failed: The operation couldn’t be completed. Protocol error
+  //
+  const noCompression =
+    userAgentParser(navigator.userAgent).browser.name === "Safari"
+      ? "&no_compression"
+      : ""
+
   const proto = location.protocol === "https:" ? "wss:" : "ws:"
   const socket = new WebSocket(
-    `${proto}//${location.host}/api/v2/workspaceagents/${agentId}/startup-logs?follow&after=${after}`,
+    `${proto}//${location.host}/api/v2/workspaceagents/${agentId}/startup-logs?follow&after=${after}${noCompression}`,
   )
   socket.binaryType = "blob"
   socket.addEventListener("message", (event) => {