diff --git a/package.json b/package.json
index 1b0829fa..7c63f0b6 100644
--- a/package.json
+++ b/package.json
@@ -42,6 +42,11 @@
           },
           "scope": "machine",
           "default": []
+        },
+        "coder.insecure": {
+          "markdownDescription": "If true, the extension will not verify the authenticity of the remote host. This is useful for self-signed certificates.",
+          "type": "boolean",
+          "default": false
         }
       }
     },
@@ -241,4 +246,4 @@
     "yaml": "^1.10.0",
     "zod": "^3.21.4"
   }
-}
+}
\ No newline at end of file
diff --git a/src/commands.ts b/src/commands.ts
index 23c03d11..079aac20 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -3,6 +3,7 @@ import { getAuthenticatedUser, getWorkspaces, updateWorkspaceVersion } from "cod
 import { Workspace, WorkspaceAgent } from "coder/site/src/api/typesGenerated"
 import * as vscode from "vscode"
 import { extractAgents } from "./api-helper"
+import { SelfSignedCertificateError } from "./error"
 import { Remote } from "./remote"
 import { Storage } from "./storage"
 import { OpenableTreeItem } from "./workspacesProvider"
@@ -61,6 +62,14 @@ export class Commands {
               if (axios.isAxiosError(err) && err.response?.data) {
                 message = err.response.data.detail
               }
+              if (err instanceof SelfSignedCertificateError) {
+                err.showInsecureNotification(this.storage)
+
+                return {
+                  message: err.message,
+                  severity: vscode.InputBoxValidationSeverity.Error,
+                }
+              }
               return {
                 message: "Invalid session token! (" + message + ")",
                 severity: vscode.InputBoxValidationSeverity.Error,
@@ -189,7 +198,10 @@ export class Commands {
             quickPick.items = items
             quickPick.busy = false
           })
-          .catch(() => {
+          .catch((ex) => {
+            if (ex instanceof SelfSignedCertificateError) {
+              ex.showInsecureNotification(this.storage)
+            }
             return
           })
       })
diff --git a/src/error.ts b/src/error.ts
new file mode 100644
index 00000000..4c247836
--- /dev/null
+++ b/src/error.ts
@@ -0,0 +1,51 @@
+import * as fs from "fs/promises"
+import * as jsonc from "jsonc-parser"
+import * as vscode from "vscode"
+import { Storage } from "./storage"
+
+export class SelfSignedCertificateError extends Error {
+  public static Notification =
+    "Your Coder deployment is using a self-signed certificate. VS Code uses a version of Electron that does not support registering self-signed intermediate certificates with extensions."
+  public static ActionAllowInsecure = "Allow Insecure"
+  public static ActionViewMoreDetails = "View More Details"
+
+  constructor(message: string) {
+    super(`Your Coder deployment is using a self-signed certificate: ${message}`)
+  }
+
+  public viewMoreDetails(): Thenable<boolean> {
+    return vscode.env.openExternal(vscode.Uri.parse("https://github.com/coder/vscode-coder/issues/105"))
+  }
+
+  // allowInsecure manually reads the settings file and updates the value of the
+  // "coder.insecure" property.
+  public async allowInsecure(storage: Storage): Promise<void> {
+    let settingsContent = "{}"
+    try {
+      settingsContent = await fs.readFile(storage.getUserSettingsPath(), "utf8")
+    } catch (ex) {
+      // Ignore! It's probably because the file doesn't exist.
+    }
+    const edits = jsonc.modify(settingsContent, ["coder.insecure"], true, {})
+    await fs.writeFile(storage.getUserSettingsPath(), jsonc.applyEdits(settingsContent, edits))
+
+    vscode.window.showInformationMessage(
+      'The Coder extension will no longer verify TLS on HTTPS requests. You can change this at any time with the "coder.insecure" property in your VS Code settings.',
+    )
+  }
+
+  public async showInsecureNotification(storage: Storage): Promise<void> {
+    const value = await vscode.window.showErrorMessage(
+      SelfSignedCertificateError.Notification,
+      SelfSignedCertificateError.ActionAllowInsecure,
+      SelfSignedCertificateError.ActionViewMoreDetails,
+    )
+    if (value === SelfSignedCertificateError.ActionViewMoreDetails) {
+      await this.viewMoreDetails()
+      return
+    }
+    if (value === SelfSignedCertificateError.ActionAllowInsecure) {
+      return this.allowInsecure(storage)
+    }
+  }
+}
diff --git a/src/extension.ts b/src/extension.ts
index e88928d6..b5aaf62c 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -1,13 +1,67 @@
 "use strict"
+import axios from "axios"
 import { getAuthenticatedUser } from "coder/site/src/api/api"
+import * as https from "https"
 import * as module from "module"
 import * as vscode from "vscode"
 import { Commands } from "./commands"
+import { SelfSignedCertificateError } from "./error"
 import { Remote } from "./remote"
 import { Storage } from "./storage"
 import { WorkspaceQuery, WorkspaceProvider } from "./workspacesProvider"
 
 export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
+  // The Remote SSH extension's proposed APIs are used to override
+  // the SSH host name in VS Code itself. It's visually unappealing
+  // having a lengthy name!
+  //
+  // This is janky, but that's alright since it provides such minimal
+  // functionality to the extension.
+  const remoteSSHExtension = vscode.extensions.getExtension("ms-vscode-remote.remote-ssh")
+  if (!remoteSSHExtension) {
+    throw new Error("Remote SSH extension not found")
+  }
+  // eslint-disable-next-line @typescript-eslint/no-explicit-any
+  const vscodeProposed: typeof vscode = (module as any)._load(
+    "vscode",
+    {
+      filename: remoteSSHExtension?.extensionPath,
+    },
+    false,
+  )
+
+  // updateInsecure is called on extension activation and when the insecure
+  // setting is changed. It updates the https agent to allow self-signed
+  // certificates if the insecure setting is true.
+  const applyInsecure = () => {
+    const insecure = Boolean(vscode.workspace.getConfiguration().get("coder.insecure"))
+
+    axios.defaults.httpsAgent = new https.Agent({
+      // rejectUnauthorized defaults to true, so we need to explicitly set it to false
+      // if we want to allow self-signed certificates.
+      rejectUnauthorized: !insecure,
+    })
+  }
+
+  axios.interceptors.response.use(
+    (r) => r,
+    (err) => {
+      if (err) {
+        const msg = err.toString() as string
+        if (msg.indexOf("unable to verify the first certificate") !== -1) {
+          throw new SelfSignedCertificateError(msg)
+        }
+      }
+
+      throw err
+    },
+  )
+
+  vscode.workspace.onDidChangeConfiguration((e) => {
+    e.affectsConfiguration("coder.insecure") && applyInsecure()
+  })
+  applyInsecure()
+
   const output = vscode.window.createOutputChannel("Coder")
   const storage = new Storage(output, ctx.globalState, ctx.secrets, ctx.globalStorageUri, ctx.logUri)
   await storage.init()
@@ -62,25 +116,6 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
     },
   })
 
-  // The Remote SSH extension's proposed APIs are used to override
-  // the SSH host name in VS Code itself. It's visually unappealing
-  // having a lengthy name!
-  //
-  // This is janky, but that's alright since it provides such minimal
-  // functionality to the extension.
-  const remoteSSHExtension = vscode.extensions.getExtension("ms-vscode-remote.remote-ssh")
-  if (!remoteSSHExtension) {
-    throw new Error("Remote SSH extension not found")
-  }
-  // eslint-disable-next-line @typescript-eslint/no-explicit-any
-  const vscodeProposed: typeof vscode = (module as any)._load(
-    "vscode",
-    {
-      filename: remoteSSHExtension?.extensionPath,
-    },
-    false,
-  )
-
   const commands = new Commands(vscodeProposed, storage)
 
   vscode.commands.registerCommand("coder.login", commands.login.bind(commands))
@@ -109,6 +144,27 @@ export async function activate(ctx: vscode.ExtensionContext): Promise<void> {
   try {
     await remote.setup(vscodeProposed.env.remoteAuthority)
   } catch (ex) {
+    if (ex instanceof SelfSignedCertificateError) {
+      const prompt = await vscodeProposed.window.showErrorMessage(
+        "Failed to open workspace",
+        {
+          detail: SelfSignedCertificateError.Notification,
+          modal: true,
+          useCustom: true,
+        },
+        SelfSignedCertificateError.ActionAllowInsecure,
+        SelfSignedCertificateError.ActionViewMoreDetails,
+      )
+      if (prompt === SelfSignedCertificateError.ActionAllowInsecure) {
+        await ex.allowInsecure(storage)
+        await remote.reloadWindow()
+        return
+      }
+      if (prompt === SelfSignedCertificateError.ActionViewMoreDetails) {
+        await ex.viewMoreDetails()
+        return
+      }
+    }
     await vscodeProposed.window.showErrorMessage("Failed to open workspace", {
       detail: (ex as string).toString(),
       modal: true,
diff --git a/src/remote.ts b/src/remote.ts
index c97430e1..5d2f1134 100644
--- a/src/remote.ts
+++ b/src/remote.ts
@@ -696,7 +696,7 @@ export class Remote {
   }
 
   // reloadWindow reloads the current window.
-  private async reloadWindow() {
+  public async reloadWindow() {
     await vscode.commands.executeCommand("workbench.action.reloadWindow")
   }
 
diff --git a/src/sshSupport.test.ts b/src/sshSupport.test.ts
index dbcde14f..8bf2ac58 100644
--- a/src/sshSupport.test.ts
+++ b/src/sshSupport.test.ts
@@ -3,6 +3,7 @@ import { computeSSHProperties, sshSupportsSetEnv, sshVersionSupportsSetEnv } fro
 
 const supports = {
   "OpenSSH_8.9p1 Ubuntu-3ubuntu0.1, OpenSSL 3.0.2 15 Mar 2022": true,
+  "OpenSSH_for_Windows_8.1p1, LibreSSL 3.0.2": true,
   "OpenSSH_9.0p1, LibreSSL 3.3.6": true,
   "OpenSSH_7.6p1 Ubuntu-4ubuntu0.7, OpenSSL 1.0.2n 7 Dec 2017": false,
   "OpenSSH_7.4p1, OpenSSL 1.0.2k-fips  26 Jan 2017": false,
diff --git a/src/sshSupport.ts b/src/sshSupport.ts
index 5726070a..12b65dd3 100644
--- a/src/sshSupport.ts
+++ b/src/sshSupport.ts
@@ -16,7 +16,7 @@ export function sshSupportsSetEnv(): boolean {
 //
 // It was introduced in SSH 7.8 and not all versions support it.
 export function sshVersionSupportsSetEnv(sshVersionString: string): boolean {
-  const match = sshVersionString.match(/OpenSSH_([\d.]+)[^,]*/)
+  const match = sshVersionString.match(/OpenSSH.*_([\d.]+)[^,]*/)
   if (match && match[1]) {
     const installedVersion = match[1]
     const parts = installedVersion.split(".")

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