diff --git a/.yarn/patches/ssh2-npm-1.11.0-convertSha1.patch b/.yarn/patches/ssh2-npm-1.11.0-convertSha1.patch
new file mode 100644
index 0000000..3e9f284
--- /dev/null
+++ b/.yarn/patches/ssh2-npm-1.11.0-convertSha1.patch
@@ -0,0 +1,96 @@
+diff --git a/lib/client.js b/lib/client.js
+index 80f372a832b71f5bfd18277af7111bdb72930125..9712c5c3f74bb08890dc458efaf8020b988918b0 100644
+--- a/lib/client.js
++++ b/lib/client.js
+@@ -388,8 +388,18 @@ class Client extends EventEmitter {
+         USERAUTH_PK_OK: (p) => {
+           if (curAuth.type === 'agent') {
+             const key = curAuth.agentCtx.currentKey();
++            let algo;
++            if (key.type === 'ssh-rsa' && curAuth.convertSha1) {
++              if (this._protocol._remoteHostKeyAlgorithms.includes('rsa-sha2-512')) {
++                debug && debug('Client: USERAUTH_PK_OK: ssh-rsa key with convertSha1 enabled, switching to sha512');
++                algo = 'sha512';
++              } else if (this._protocol._remoteHostKeyAlgorithms.includes('rsa-sha2-256')) {
++                debug && debug('Client: USERAUTH_PK_OK: ssh-rsa key with convertSha1 enabled, switching to sha256');
++                algo = 'sha256';
++              }
++            }
+             proto.authPK(curAuth.username, key, (buf, cb) => {
+-              curAuth.agentCtx.sign(key, buf, {}, (err, signed) => {
++              curAuth.agentCtx.sign(key, buf, { hash: algo }, (err, signed) => {
+                 if (err) {
+                   err.level = 'agent';
+                   this.emit('error', err);
+@@ -401,8 +411,18 @@ class Client extends EventEmitter {
+               });
+             });
+           } else if (curAuth.type === 'publickey') {
++            let algo;
++            if (curAuth.key.type === 'ssh-rsa' && curAuth.convertSha1) {
++              if (this._protocol._remoteHostKeyAlgorithms.includes('rsa-sha2-512')) {
++                debug && debug('Client: USERAUTH_PK_OK: ssh-rsa key with convertSha1 enabled, switching to sha512');
++                algo = 'sha512';
++              } else if (this._protocol._remoteHostKeyAlgorithms.includes('rsa-sha2-256')) {
++                debug && debug('Client: USERAUTH_PK_OK: ssh-rsa key with convertSha1 enabled, switching to sha256');
++                algo = 'sha256';
++              }
++            }
+             proto.authPK(curAuth.username, curAuth.key, (buf, cb) => {
+-              const signature = curAuth.key.sign(buf);
++              const signature = curAuth.key.sign(buf, algo);
+               if (signature instanceof Error) {
+                 signature.message =
+                   `Error signing data with key: ${signature.message}`;
+@@ -881,7 +901,7 @@ class Client extends EventEmitter {
+               return skipAuth('Skipping invalid key auth attempt');
+             if (!key.isPrivateKey())
+               return skipAuth('Skipping non-private key');
+-            nextAuth = { type, username, key };
++            nextAuth = { type, username, key, convertSha1: nextAuth.convertSha1 };
+             break;
+           }
+           case 'hostbased': {
+@@ -906,7 +926,7 @@ class Client extends EventEmitter {
+                 `Skipping invalid agent: ${nextAuth.agent}`
+               );
+             }
+-            nextAuth = { type, username, agentCtx: new AgentContext(agent) };
++            nextAuth = { type, username, agentCtx: new AgentContext(agent), convertSha1: nextAuth.convertSha1 };
+             break;
+           }
+           case 'keyboard-interactive': {
+diff --git a/lib/protocol/Protocol.js b/lib/protocol/Protocol.js
+index 94e12bc72b5c61094efd6862dfbce6ff852c5b26..e0cbb748bc80455bfa819cc20c672701c280409c 100644
+--- a/lib/protocol/Protocol.js
++++ b/lib/protocol/Protocol.js
+@@ -616,7 +616,15 @@ class Protocol {
+     if (pubKey instanceof Error)
+       throw new Error('Invalid key');
+ 
+-    const keyType = pubKey.type;
++    let keyType = pubKey.type;
++    if (keyType === 'ssh-rsa') {
++      for (const algo of ['rsa-sha2-512', 'rsa-sha2-256']) {
++        if (this._remoteHostKeyAlgorithms.includes(algo)) {
++         keyType = algo;
++         break;
++        }
++      }
++    }
+     pubKey = pubKey.getPublicSSH();
+ 
+     const userLen = Buffer.byteLength(username);
+diff --git a/lib/protocol/kex.js b/lib/protocol/kex.js
+index 49b28f54677809c32b2141c99eec36e0c6d99e38..4ee69bd3b3b5685665d69c05114a94c14cd4b076 100644
+--- a/lib/protocol/kex.js
++++ b/lib/protocol/kex.js
+@@ -196,6 +196,8 @@ function handleKexInit(self, payload) {
+ 
+   const local = self._offer;
+   const remote = init;
++  
++  self._remoteHostKeyAlgorithms = remote.serverHostKey;
+ 
+   let localKex = local.lists.kex.array;
+   if (self._compatFlags & COMPAT.BAD_DHGEX) {
diff --git a/.yarn/yarn.lock b/.yarn/yarn.lock
index ed53231..404b909 100644
--- a/.yarn/yarn.lock
+++ b/.yarn/yarn.lock
@@ -8799,7 +8799,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"ssh2@npm:^1.11.0":
+"ssh2@npm:1.11.0":
   version: 1.11.0
   resolution: "ssh2@npm:1.11.0"
   dependencies:
@@ -8816,6 +8816,23 @@ __metadata:
   languageName: node
   linkType: hard
 
+"ssh2@patch:ssh2@npm%3A1.11.0#./.yarn/patches/ssh2-npm-1.11.0-convertSha1.patch::locator=vscode-sshfs%40workspace%3A.":
+  version: 1.11.0
+  resolution: "ssh2@patch:ssh2@npm%3A1.11.0#./.yarn/patches/ssh2-npm-1.11.0-convertSha1.patch::version=1.11.0&hash=602c9b&locator=vscode-sshfs%40workspace%3A."
+  dependencies:
+    asn1: ^0.2.4
+    bcrypt-pbkdf: ^1.0.2
+    cpu-features: ~0.0.4
+    nan: ^2.16.0
+  dependenciesMeta:
+    cpu-features:
+      optional: true
+    nan:
+      optional: true
+  checksum: f33a0074637f195b261952cea4b8b02c15977375f59d985580c0c571ac6bac56cf523cd85ee99d1fdcdcce4e6547271c35b2450c0c14963f11ff88b0093d8b8e
+  languageName: node
+  linkType: hard
+
 "ssri@npm:^9.0.0":
   version: 9.0.1
   resolution: "ssri@npm:9.0.1"
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 766120e..bc36f44 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,17 @@
 
 # Changelog
 
+## Unreleased
+
+### Changes
+
+- Apply a patch to ssh2 and make use of it to fix OpenSSH 8.8+ disabling `ssh-rsa` (SHA1) by default (#309)
+  - Patch file in `.yarn/patches` based on <https://github.com/Eugeny/ssh2/tree/rsa-sha> applied to `ssh2@1.11.0`
+  - The patch adds an option `convertSha1` to `publickey` and `agent` authentication methods on top of Eugeny's modifications
+    - When the option is present, `ssh-rsa` keys will be treated as `rsa-sha2-512` or `rsa-sha2-256`, if the server supports it
+  - Added a flag `OPENSSH-SHA1` (enabled by default) to pass this `convertSha1` flag when using `publickey` or `agent` auths
+  - Part of this change required creating a custom ssh2 `authHandler` (based on the built-in version) to pass the option if desired
+
 ## v1.26.0 (2023-03-25)
 
 ### Changes
diff --git a/common/src/ssh2.ts b/common/src/ssh2.ts
index e49b3ca..ae7c3f4 100644
--- a/common/src/ssh2.ts
+++ b/common/src/ssh2.ts
@@ -110,6 +110,8 @@ declare module 'ssh2' {
         key: string | Buffer | ParsedKey;
         /** Optional passphrase in case `key` is an encrypted key */
         passphrase?: string;
+        /** [PATCH:convertSha1#309] If true, make ssh-rsa keys use sha512/sha256 instead of sha1 if possible */
+        convertSha1?: boolean;
     }
     export interface AuthHandlerHostBased {
         type: 'hostbased';
@@ -125,6 +127,8 @@ declare module 'ssh2' {
         type: 'agent';
         username: string;
         agent: string | BaseAgent;
+        /** [PATCH:convertSha1#309] If true, make ssh-rsa keys use sha512/sha256 instead of sha1 if possible */
+        convertSha1?: boolean;
     }
     export interface AuthHandlerKeyboardInteractive {
         type: 'keyboard-interactive';
diff --git a/package.json b/package.json
index 26bc339..7fe9552 100644
--- a/package.json
+++ b/package.json
@@ -436,7 +436,8 @@
         "winreg": "^1.2.4"
     },
     "resolutions": {
-        "cpu-features": "npm:@favware/skip-dependency@1.1.3"
+        "cpu-features": "npm:@favware/skip-dependency@1.1.3",
+        "ssh2@^1.11.0": "patch:ssh2@npm%3A1.11.0#./.yarn/patches/ssh2-npm-1.11.0-convertSha1.patch"
     },
     "workspaces": [
         "./common",
diff --git a/src/connect.ts b/src/connect.ts
index 41f4f69..4f3c3d0 100644
--- a/src/connect.ts
+++ b/src/connect.ts
@@ -2,12 +2,12 @@ import type { FileSystemConfig } from 'common/fileSystemConfig';
 import { readFile } from 'fs';
 import { Socket } from 'net';
 import { userInfo } from 'os';
-import { Client, ClientChannel, ConnectConfig } from 'ssh2';
+import { AuthHandlerFunction, AuthHandlerObject, Client, ClientChannel, ConnectConfig } from 'ssh2';
 import { SFTP } from 'ssh2/lib/protocol/SFTP';
 import * as vscode from 'vscode';
 import { getConfig } from './config';
 import { getFlagBoolean } from './flags';
-import { Logging } from './logging';
+import { Logger, Logging } from './logging';
 import type { PuttySession } from './putty';
 import { toPromise, validatePort } from './utils';
 
@@ -225,6 +225,34 @@ export async function createSocket(config: FileSystemConfig): Promise<NodeJS.Rea
   });
 }
 
+function makeAuthHandler(config: FileSystemConfig, logging: Logger): AuthHandlerFunction {
+  const authsAllowed: (AuthHandlerObject | AuthHandlerObject['type'])[] = ['none'];
+  const [flagV, flagR] = getFlagBoolean('OPENSSH-SHA1', true, config.flags);
+  if (config.password) authsAllowed.push('password');
+  if (config.privateKey) {
+    if (flagV) {
+      logging.info`Flag "OPENSSH-SHA1" enabled due to '${flagR}', including convertSha1 for publickey authentication`;
+      authsAllowed.push({ type: 'publickey', username: config.username!, key: config.privateKey, convertSha1: true });
+    } else {
+      authsAllowed.push('publickey');
+    }
+  }
+  if (config.agent) {
+    if (flagV) {
+      logging.info`Flag "OPENSSH-SHA1" enabled due to '${flagR}', including convertSha1 for agent authentication`;
+      authsAllowed.push({ type: 'agent', username: config.username!, agent: config.agent, convertSha1: true });
+    } else {
+      authsAllowed.push('agent');
+    }
+  }
+  if (config.tryKeyboard) authsAllowed.push('keyboard-interactive');
+  if (config.privateKey && config.localHostname && config.localUsername) authsAllowed.push('hostbased');
+  if (flagV) {
+    logging.info`Flag "OPENSSH-SHA1" enabled due to '${flagR}'`;
+  }
+  return () => authsAllowed.shift() || false;
+}
+
 export async function createSSH(config: FileSystemConfig, sock?: NodeJS.ReadableStream): Promise<Client | null> {
   config = (await calculateActualConfig(config))!;
   if (!config) return null;
@@ -253,7 +281,8 @@ export async function createSSH(config: FileSystemConfig, sock?: NodeJS.Readable
       reject(error);
     });
     try {
-      const finalConfig: ConnectConfig = { ...config, sock, ...DEFAULT_CONFIG };
+      const finalConfig: FileSystemConfig = { ...config, sock, ...DEFAULT_CONFIG };
+      finalConfig.authHandler = makeAuthHandler(finalConfig, logging);
       if (config.debug || getFlagBoolean('DEBUG_SSH2', false, config.flags)[0]) {
         const scope = Logging.scope(`ssh2(${config.name})`);
         finalConfig.debug = (msg: string) => scope.debug(msg);
diff --git a/src/flags.ts b/src/flags.ts
index 637fd47..941fa6a 100644
--- a/src/flags.ts
+++ b/src/flags.ts
@@ -8,6 +8,11 @@ import { catchingPromise } from './utils';
     - Disables the 'diffie-hellman-group-exchange' kex algorithm as a default option
     - Originally for issue #239
     - Automatically enabled for Electron v11.0, v11.1 and v11.2
+  OPENSSH-SHA1 (boolean) (default=true)
+    - Patch for issue #309 where OpenSSH 8.8+ refuses `ssh-rsa` keys using SHA1 (which is what ssh2 uses)
+    - The patch (see `.yarn/patches/*-convertSha1.patch`) adds an option for `agent` and `publickey` authentications
+    - With this option enabled, the patch will, if the server supports it, make ssh2 use SHA512/SHA256 for `ssh-rsa` keys
+    / Mind that this option applies for every server, the patch doesn't (currently) check whether it's OpenSSH 8.8+
   DEBUG_SSH2 (boolean) (default=false)
     - Enables debug logging in the ssh2 library (set at the start of each connection)
   WINDOWS_COMMAND_SEPARATOR (boolean) (default=false)