diff --git a/agent/bindings/kotlin/lib/src/main/kotlin/com/sourcegraph/cody/agent/protocol_generated/CodyAgentServer.kt b/agent/bindings/kotlin/lib/src/main/kotlin/com/sourcegraph/cody/agent/protocol_generated/CodyAgentServer.kt
index ac8dfb8710a5..30f8f6bf42ce 100644
--- a/agent/bindings/kotlin/lib/src/main/kotlin/com/sourcegraph/cody/agent/protocol_generated/CodyAgentServer.kt
+++ b/agent/bindings/kotlin/lib/src/main/kotlin/com/sourcegraph/cody/agent/protocol_generated/CodyAgentServer.kt
@@ -136,6 +136,8 @@ interface CodyAgentServer {
   fun ignore_test(params: Ignore_TestParams): CompletableFuture<Ignore_TestResult>
   @JsonRequest("testing/ignore/overridePolicy")
   fun testing_ignore_overridePolicy(params: ContextFilters?): CompletableFuture<Null?>
+  @JsonRequest("extension/reset")
+  fun extension_reset(params: Null?): CompletableFuture<Null?>
 
   // =============
   // Notifications
diff --git a/agent/package.json b/agent/package.json
index 95327f4aa175..75270bb094f3 100644
--- a/agent/package.json
+++ b/agent/package.json
@@ -44,7 +44,6 @@
     "csv-writer": "^1.6.0",
     "dedent": "^0.7.0",
     "easy-table": "^1.2.0",
-    "env-paths": "^3.0.0",
     "fast-myers-diff": "^3.2.0",
     "glob": "^11.0.0",
     "js-levenshtein": "^1.1.6",
diff --git a/agent/src/agent.ts b/agent/src/agent.ts
index 58e16addd077..13ddb904a135 100644
--- a/agent/src/agent.ts
+++ b/agent/src/agent.ts
@@ -44,6 +44,7 @@ import type * as agent_protocol from '../../vscode/src/jsonrpc/agent-protocol'
 import { mkdirSync, statSync } from 'node:fs'
 import { PassThrough } from 'node:stream'
 import type { Har } from '@pollyjs/persister'
+import { codyPaths } from '@sourcegraph/cody-shared'
 import { TESTING_TELEMETRY_EXPORTER } from '@sourcegraph/cody-shared/src/telemetry-v2/TelemetryRecorderProvider'
 import { type TelemetryEventParameters, TestTelemetryExporter } from '@sourcegraph/telemetry'
 import { copySync } from 'fs-extra'
@@ -76,7 +77,6 @@ import { AgentWorkspaceConfiguration } from './AgentWorkspaceConfiguration'
 import { AgentWorkspaceDocuments } from './AgentWorkspaceDocuments'
 import { registerNativeWebviewHandlers, resolveWebviewView } from './NativeWebview'
 import type { PollyRequestError } from './cli/command-jsonrpc-stdio'
-import { codyPaths } from './codyPaths'
 import {
     currentProtocolAuthStatus,
     currentProtocolAuthStatusOrNotReadyYet,
@@ -967,6 +967,11 @@ export class Agent extends MessageHandler implements ExtensionClient {
             }
         })
 
+        this.registerAuthenticatedRequest('extension/reset', async () => {
+            await this.globalState?.reset()
+            return null
+        })
+
         this.registerNotification('autocomplete/completionAccepted', async ({ completionID }) => {
             const provider = await vscode_shim.completionProvider()
             await provider.handleDidAcceptCompletionItem(completionID as CompletionItemID)
diff --git a/agent/src/cli/command-auth/settings.ts b/agent/src/cli/command-auth/settings.ts
index fc16002ab781..5e44d116b08c 100644
--- a/agent/src/cli/command-auth/settings.ts
+++ b/agent/src/cli/command-auth/settings.ts
@@ -1,7 +1,7 @@
 import fs from 'node:fs'
 
 import path from 'node:path'
-import { codyPaths } from '../../codyPaths'
+import { codyPaths } from '@sourcegraph/cody-shared'
 
 export interface Account {
     // In most cases, the ID will be the same as the username.  It's only when
diff --git a/agent/src/cli/command-bench/command-bench.ts b/agent/src/cli/command-bench/command-bench.ts
index bc76e6ba4f94..169530c8ed6e 100644
--- a/agent/src/cli/command-bench/command-bench.ts
+++ b/agent/src/cli/command-bench/command-bench.ts
@@ -10,7 +10,7 @@ import { newAgentClient } from '../../agent'
 import { exec } from 'node:child_process'
 import fs from 'node:fs'
 import { promisify } from 'node:util'
-import { isDefined, modelsService, setClientCapabilities } from '@sourcegraph/cody-shared'
+import { codyPaths, isDefined, modelsService, setClientCapabilities } from '@sourcegraph/cody-shared'
 import { sleep } from '../../../../vscode/src/completions/utils'
 import {
     getConfiguration,
@@ -21,7 +21,6 @@ import { createOrUpdateTelemetryRecorderProvider } from '../../../../vscode/src/
 import { startPollyRecording } from '../../../../vscode/src/testutils/polly'
 import { dotcomCredentials } from '../../../../vscode/src/testutils/testing-credentials'
 import { allClientCapabilitiesEnabled } from '../../allClientCapabilitiesEnabled'
-import { codyPaths } from '../../codyPaths'
 import { arrayOption, booleanOption, intOption } from './cli-parsers'
 import { matchesGlobPatterns } from './matchesGlobPatterns'
 import { evaluateAutocompleteStrategy } from './strategy-autocomplete'
diff --git a/agent/src/esbuild.mjs b/agent/src/esbuild.mjs
index 12dc91442acb..777c6b4f96be 100644
--- a/agent/src/esbuild.mjs
+++ b/agent/src/esbuild.mjs
@@ -1,6 +1,8 @@
 import fs from 'node:fs/promises'
 import path from 'node:path'
 import process from 'node:process'
+// @ts-ignore this is not compiled by typescript so it can import files from outside the rootDir
+import { detectForbiddenImportPlugin } from '../../lib/shared/esbuild.utils.mjs'
 
 import { build } from 'esbuild'
 
@@ -65,7 +67,7 @@ async function buildAgent() {
             '@sourcegraph/cody-shared/src': '@sourcegraph/cody-shared/src',
         },
     }
-    const res = await build(esbuildOptions)
+    await build(esbuildOptions)
 
     // Copy all .wasm files to the dist/ directory
     const distDir = path.join(process.cwd(), '..', 'vscode', 'dist')
@@ -83,24 +85,3 @@ async function buildAgent() {
         await fs.copyFile(src, dest)
     }
 }
-
-function detectForbiddenImportPlugin(allForbiddenModules) {
-    return {
-        name: 'detect-forbidden-import-plugin',
-        setup(build) {
-            build.onResolve({ filter: /.*/ }, args => {
-                for (const forbidden of allForbiddenModules) {
-                    if (args.path === forbidden) {
-                        throw new Error(`'${forbidden}' module is imported in file: ${args.importer}`)
-                    }
-                }
-                args
-            })
-
-            build.onLoad({ filter: /.*/ }, async args => {
-                const contents = await fs.readFile(args.path, 'utf8')
-                return { contents, loader: 'default' }
-            })
-        },
-    }
-}
diff --git a/agent/src/global-state/AgentGlobalState.ts b/agent/src/global-state/AgentGlobalState.ts
index ce594be9c471..1d96411768f4 100644
--- a/agent/src/global-state/AgentGlobalState.ts
+++ b/agent/src/global-state/AgentGlobalState.ts
@@ -45,12 +45,10 @@ export class AgentGlobalState implements vscode.Memento {
     }
 
     public async reset(): Promise<void> {
-        if (this.db instanceof InMemoryDB) {
-            this.db.clear()
+        this.db.clear()
 
-            // HACK(sqs): Force `localStorage` to fire a change event.
-            await localStorage.delete('')
-        }
+        // HACK(sqs): Force `localStorage` to fire a change event.
+        await localStorage.delete('')
     }
 
     public keys(): readonly string[] {
@@ -91,6 +89,7 @@ interface DB {
     get(key: string): any
     set(key: string, value: any): void
     keys(): readonly string[]
+    clear(): void
 }
 
 class InMemoryDB implements DB {
@@ -120,6 +119,9 @@ class LocalStorageDB implements DB {
         const quota = 1024 * 1024 * 256 // 256 MB
         this.storage = new LocalStorage(path.join(dir, `${ide}-globalState`), quota)
     }
+    clear() {
+        this.storage.clear()
+    }
 
     get(key: string): any {
         const item = this.storage.getItem(key)
diff --git a/agent/tsconfig.json b/agent/tsconfig.json
index d1b66575797c..72287b695456 100644
--- a/agent/tsconfig.json
+++ b/agent/tsconfig.json
@@ -5,9 +5,21 @@
     "rootDir": ".",
     "outDir": "dist",
     "target": "es2019",
-    "allowJs": true,
+    "allowJs": false
   },
-  "include": ["**/*", ".*", "package.json", "src/language-file-extensions.json"],
-  "exclude": ["dist", "bindings", "src/__tests__", "vitest.config.ts", "typehacks"],
-  "references": [{ "path": "../lib/shared" }, { "path": "../vscode" }],
+  "include": [
+    "**/*",
+    ".*",
+    "package.json",
+    "src/language-file-extensions.json"
+  ],
+  "exclude": [
+    "dist",
+    "bindings",
+    "src/__tests__",
+    "vitest.config.ts",
+    "typehacks",
+    "*.mjs"
+  ],
+  "references": [{ "path": "../lib/shared" }, { "path": "../vscode" }]
 }
diff --git a/lib/shared/esbuild.utils.mjs b/lib/shared/esbuild.utils.mjs
new file mode 100644
index 000000000000..f97bc888db93
--- /dev/null
+++ b/lib/shared/esbuild.utils.mjs
@@ -0,0 +1,22 @@
+import fs from 'node:fs/promises'
+
+export function detectForbiddenImportPlugin(allForbiddenModules) {
+    return {
+        name: 'detect-forbidden-import-plugin',
+        setup(build) {
+            build.onResolve({ filter: /.*/ }, args => {
+                for (const forbidden of allForbiddenModules) {
+                    if (args.path === forbidden) {
+                        throw new Error(`'${forbidden}' module is imported in file: ${args.importer}`)
+                    }
+                }
+                args
+            })
+
+            build.onLoad({ filter: /.*/ }, async args => {
+                const contents = await fs.readFile(args.path, 'utf8')
+                return { contents, loader: 'default' }
+            })
+        },
+    }
+}
diff --git a/lib/shared/package.json b/lib/shared/package.json
index 6b4de55c5a25..3ecd31f0a970 100644
--- a/lib/shared/package.json
+++ b/lib/shared/package.json
@@ -25,6 +25,7 @@
     "date-fns": "^2.30.0",
     "dedent": "^0.7.0",
     "diff": "^5.2.0",
+    "env-paths": "^2.2.1",
     "immer": "^10.1.1",
     "isomorphic-fetch": "^3.0.0",
     "js-tiktoken": "^1.0.14",
diff --git a/lib/shared/src/auth/types.ts b/lib/shared/src/auth/types.ts
index b770f282021a..162881d6bae0 100644
--- a/lib/shared/src/auth/types.ts
+++ b/lib/shared/src/auth/types.ts
@@ -51,16 +51,14 @@ export interface UnauthenticatedAuthStatus {
 }
 
 export const AUTH_STATUS_FIXTURE_AUTHED: AuthenticatedAuthStatus = {
-    // this typecast is necessary to prevent codegen from becoming too specific
-    endpoint: 'https://example.com' as string,
+    endpoint: 'https://example.com',
     authenticated: true,
     username: 'alice',
     pendingValidation: false,
 }
 
 export const AUTH_STATUS_FIXTURE_UNAUTHED: AuthStatus & { authenticated: false } = {
-    // this typecast is necessary to prevent codegen from becoming too specific
-    endpoint: 'https://example.com' as string,
+    endpoint: 'https://example.com',
     authenticated: false,
     pendingValidation: false,
 }
diff --git a/agent/src/codyPaths.ts b/lib/shared/src/codyPaths.ts
similarity index 100%
rename from agent/src/codyPaths.ts
rename to lib/shared/src/codyPaths.ts
diff --git a/lib/shared/src/configuration/resolver.ts b/lib/shared/src/configuration/resolver.ts
index c88b630beb99..331309fbfc7f 100644
--- a/lib/shared/src/configuration/resolver.ts
+++ b/lib/shared/src/configuration/resolver.ts
@@ -19,6 +19,10 @@ export interface ConfigurationInput {
     clientConfiguration: ClientConfiguration
     clientSecrets: ClientSecrets
     clientState: ClientState
+    reinstall: {
+        isReinstalling(): Promise<boolean>
+        onReinstall(): Promise<void>
+    }
 }
 
 export interface ClientSecrets {
@@ -42,6 +46,7 @@ export type ResolvedConfiguration = ReadonlyDeep<{
     configuration: ClientConfiguration
     auth: AuthCredentials
     clientState: ClientState
+    isReinstall: boolean
 }>
 
 /**
@@ -67,29 +72,39 @@ export type PickResolvedConfiguration<Keys extends KeysSpec> = {
           : undefined
 }
 
-async function resolveConfiguration(input: ConfigurationInput): Promise<ResolvedConfiguration> {
+async function resolveConfiguration({
+    clientConfiguration,
+    clientSecrets,
+    clientState,
+    reinstall: { isReinstalling, onReinstall },
+}: ConfigurationInput): Promise<ResolvedConfiguration> {
+    const isReinstall = await isReinstalling()
+    if (isReinstall) {
+        await onReinstall()
+    }
     // we allow for overriding the server endpoint from config if we haven't
     // manually signed in somewhere else
     const serverEndpoint = normalizeServerEndpointURL(
-        input.clientConfiguration.overrideServerEndpoint ||
-            (input.clientState.lastUsedEndpoint ?? DOTCOM_URL.toString())
+        clientConfiguration.overrideServerEndpoint ||
+            (clientState.lastUsedEndpoint ?? DOTCOM_URL.toString())
     )
 
     // We must not throw here, because that would result in the `resolvedConfig` observable
     // terminating and all callers receiving no further config updates.
     const loadTokenFn = () =>
-        input.clientSecrets.getToken(serverEndpoint).catch(error => {
+        clientSecrets.getToken(serverEndpoint).catch(error => {
             logError(
                 'resolveConfiguration',
                 `Failed to get access token for endpoint ${serverEndpoint}: ${error}`
             )
             return null
         })
-    const accessToken = input.clientConfiguration.overrideAuthToken || ((await loadTokenFn()) ?? null)
+    const accessToken = clientConfiguration.overrideAuthToken || ((await loadTokenFn()) ?? null)
     return {
-        configuration: input.clientConfiguration,
-        clientState: input.clientState,
+        configuration: clientConfiguration,
+        clientState,
         auth: { accessToken, serverEndpoint },
+        isReinstall,
     }
 }
 
diff --git a/lib/shared/src/index.ts b/lib/shared/src/index.ts
index 49dc4d968586..f98bb80b7dea 100644
--- a/lib/shared/src/index.ts
+++ b/lib/shared/src/index.ts
@@ -107,6 +107,7 @@ export {
     LARGE_FILE_WARNING_LABEL,
     NO_SYMBOL_MATCHES_HELP_LABEL,
 } from './codebase-context/messages'
+export * from './codyPaths'
 export type {
     CodyCommand,
     CodyCommandContext,
diff --git a/lib/shared/tsconfig.json b/lib/shared/tsconfig.json
index 15c112b36e89..38557f8fae93 100644
--- a/lib/shared/tsconfig.json
+++ b/lib/shared/tsconfig.json
@@ -4,18 +4,9 @@
     "module": "ESNext",
     "rootDir": "src",
     "outDir": "dist",
-    "lib": [
-      "ESNext",
-      "DOM",
-      "DOM.Iterable"
-    ],
-    "moduleResolution": "Bundler",
+    "lib": ["ESNext", "DOM", "DOM.Iterable"],
+    "moduleResolution": "Bundler"
   },
-  "include": [
-    "src",
-  ],
-  "exclude": [
-    "dist",
-    "typehacks"
-  ],
+  "include": ["src"],
+  "exclude": ["dist", "typehacks", "*.mjs"]
 }
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index d6d5d835072b..88926bfe5a9f 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -356,6 +356,9 @@ importers:
       diff:
         specifier: ^5.2.0
         version: 5.2.0
+      env-paths:
+        specifier: ^2.2.1
+        version: 2.2.1
       immer:
         specifier: ^10.1.1
         version: 10.1.1
@@ -743,8 +746,8 @@ importers:
         specifier: ^1.79.0
         version: 1.80.0
       '@vscode/test-electron':
-        specifier: ^2.3.8
-        version: 2.3.8
+        specifier: ^2.4.0
+        version: 2.4.0
       '@vscode/test-web':
         specifier: ^0.0.47
         version: 0.0.47
@@ -6262,11 +6265,6 @@ packages:
       react-dom: 18.2.0(react@18.2.0)
     dev: true
 
-  /@tootallnate/once@1.1.2:
-    resolution: {integrity: sha512-RbzJvlNzmRq5c3O09UipeuXno4tA1FE6ikOjxZK0tuxVv3412l64l5t1W5pj4+rJq9vpkm/kwiR07aZXnsKPxw==}
-    engines: {node: '>= 6'}
-    dev: true
-
   /@tootallnate/once@2.0.0:
     resolution: {integrity: sha512-XCuKFP5PS55gnMVu3dty8KPatLqUoy/ZYzDzAGCQ8JNFCkLXzmI7vNHCR+XpbZaMWQK/vQubr7PkYq8g470J/A==}
     engines: {node: '>= 10'}
@@ -6891,14 +6889,15 @@ packages:
   /@vscode/codicons@0.0.35:
     resolution: {integrity: sha512-7iiKdA5wHVYSbO7/Mm0hiHD3i4h+9hKUe1O4hISAe/nHhagMwb2ZbFC8jU6d7Cw+JNT2dWXN2j+WHbkhT5/l2w==}
 
-  /@vscode/test-electron@2.3.8:
-    resolution: {integrity: sha512-b4aZZsBKtMGdDljAsOPObnAi7+VWIaYl3ylCz1jTs+oV6BZ4TNHcVNC3xUn0azPeszBmwSBDQYfFESIaUQnrOg==}
+  /@vscode/test-electron@2.4.0:
+    resolution: {integrity: sha512-yojuDFEjohx6Jb+x949JRNtSn6Wk2FAh4MldLE3ck9cfvCqzwxF32QsNy1T9Oe4oT+ZfFcg0uPUCajJzOmPlTA==}
     engines: {node: '>=16'}
     dependencies:
-      http-proxy-agent: 4.0.1
-      https-proxy-agent: 5.0.1
+      http-proxy-agent: 7.0.2
+      https-proxy-agent: 7.0.4
       jszip: 3.10.1
-      semver: 7.6.0
+      ora: 7.0.1
+      semver: 7.6.3
     transitivePeerDependencies:
       - supports-color
     dev: true
@@ -7537,6 +7536,14 @@ packages:
       readable-stream: 3.6.2
     dev: true
 
+  /bl@5.1.0:
+    resolution: {integrity: sha512-tv1ZJHLfTDnXE6tMHv73YgSJaWR2AFuPwMntBe7XL/GBFHnT0CLnsHMogfk5+GzCDC5ZWarSCYaIGATZt9dNsQ==}
+    dependencies:
+      buffer: 6.0.3
+      inherits: 2.0.4
+      readable-stream: 3.6.2
+    dev: true
+
   /bluebird@3.4.7:
     resolution: {integrity: sha512-iD3898SR7sWVRHbiQv+sHUtHnMvC1o3nW5rAcqnq3uOn07DSAppZYUkIGslDz6gXC7HfunPe7YVBgoEJASPcHA==}
     dev: false
@@ -10279,17 +10286,6 @@ packages:
     transitivePeerDependencies:
       - supports-color
 
-  /http-proxy-agent@4.0.1:
-    resolution: {integrity: sha512-k0zdNgqWTGA6aeIRVpvfVob4fL52dTfaehylg0Y4UvSySvOq/Y+BOyPrgpUrA7HylqvU8vIZGsRuXmspskV0Tg==}
-    engines: {node: '>= 6'}
-    dependencies:
-      '@tootallnate/once': 1.1.2
-      agent-base: 6.0.2
-      debug: 4.3.5
-    transitivePeerDependencies:
-      - supports-color
-    dev: true
-
   /http-proxy-agent@5.0.0:
     resolution: {integrity: sha512-n2hY8YdoRE1i7r6M0w9DIw5GgZN0G25P8zLCRQ8rjXtTU3vsNFBI/vWK/UIeE6g5MUUz6avwAPXmL6Fy9D/90w==}
     engines: {node: '>= 6'}
@@ -11416,6 +11412,14 @@ packages:
       is-unicode-supported: 0.1.0
     dev: true
 
+  /log-symbols@5.1.0:
+    resolution: {integrity: sha512-l0x2DvrW294C9uDCoQe1VSU4gf529FkSZ6leBl4TiqZH/e+0R7hSfHQBNut2mNygDgHwvYHfFLn6Oxb3VWj2rA==}
+    engines: {node: '>=12'}
+    dependencies:
+      chalk: 5.3.0
+      is-unicode-supported: 1.3.0
+    dev: true
+
   /log-symbols@6.0.0:
     resolution: {integrity: sha512-i24m8rpwhmPIS4zscNzK6MSEhk0DUWa/8iYQWxhffV8jkI4Phvs3F+quL5xvS0gdQR0FyTCMMH33Y78dDTzzIw==}
     engines: {node: '>=18'}
@@ -12816,6 +12820,21 @@ packages:
       wcwidth: 1.0.1
     dev: true
 
+  /ora@7.0.1:
+    resolution: {integrity: sha512-0TUxTiFJWv+JnjWm4o9yvuskpEJLXTcng8MJuKd+SzAzp2o+OP3HWqNhB4OdJRt1Vsd9/mR0oyaEYlOnL7XIRw==}
+    engines: {node: '>=16'}
+    dependencies:
+      chalk: 5.3.0
+      cli-cursor: 4.0.0
+      cli-spinners: 2.9.2
+      is-interactive: 2.0.0
+      is-unicode-supported: 1.3.0
+      log-symbols: 5.1.0
+      stdin-discarder: 0.1.0
+      string-width: 6.1.0
+      strip-ansi: 7.1.0
+    dev: true
+
   /ora@8.0.1:
     resolution: {integrity: sha512-ANIvzobt1rls2BDny5fWZ3ZVKyD6nscLvfFRpQgfWsythlcsVUC9kL0zq6j2Z5z9wwp1kd7wpsD/T9qNPVLCaQ==}
     engines: {node: '>=18'}
@@ -14346,6 +14365,12 @@ packages:
     dependencies:
       lru-cache: 6.0.0
 
+  /semver@7.6.3:
+    resolution: {integrity: sha512-oVekP1cKtI+CTDvHWYFUcMtsK/00wmAEfyqKfNdARm8u1wNVhSgaX7A8d4UuIlUI5e84iEwOhs7ZPYRmzU9U6A==}
+    engines: {node: '>=10'}
+    hasBin: true
+    dev: true
+
   /send@0.18.0:
     resolution: {integrity: sha512-qqWzuOjSFOuqPjFe4NOsMLafToQQwBSOEpS+FwEt3A2V3vKubTquT3vmLTQpFgMXp8AlFWFuP1qKaJZOtPpVXg==}
     engines: {node: '>= 0.8.0'}
@@ -14716,6 +14741,13 @@ packages:
     resolution: {integrity: sha512-JPbdCEQLj1w5GilpiHAx3qJvFndqybBysA3qUOnznweH4QbNYUsW/ea8QzSrnh0vNsezMMw5bcVool8lM0gwzg==}
     dev: true
 
+  /stdin-discarder@0.1.0:
+    resolution: {integrity: sha512-xhV7w8S+bUwlPTb4bAOUQhv8/cSS5offJuX8GQGq32ONF0ZtDWKfkdomM3HMRA+LhX6um/FZ0COqlwsjD53LeQ==}
+    engines: {node: ^12.20.0 || ^14.13.1 || >=16.0.0}
+    dependencies:
+      bl: 5.1.0
+    dev: true
+
   /stdin-discarder@0.2.2:
     resolution: {integrity: sha512-UhDfHmA92YAlNnCfhmq0VeNL5bDbiZGg7sZ2IvPsXubGkiNa9EC+tUTsjBRsYUAz87btI6/1wf4XoVvQ3uRnmQ==}
     engines: {node: '>=18'}
@@ -14795,6 +14827,15 @@ packages:
       emoji-regex: 9.2.2
       strip-ansi: 7.1.0
 
+  /string-width@6.1.0:
+    resolution: {integrity: sha512-k01swCJAgQmuADB0YIc+7TuatfNvTBVOoaUWJjTB9R4VJzR5vNWzf5t42ESVZFPS8xTySF7CAdV4t/aaIm3UnQ==}
+    engines: {node: '>=16'}
+    dependencies:
+      eastasianwidth: 0.2.0
+      emoji-regex: 10.3.0
+      strip-ansi: 7.1.0
+    dev: true
+
   /string-width@7.1.0:
     resolution: {integrity: sha512-SEIJCWiX7Kg4c129n48aDRwLbFb2LJmXXFrWBG4NGaRtMQ3myKPKbwrD1BKqQn74oCoNMBVrfDEr5M9YxCsrkw==}
     engines: {node: '>=18'}
diff --git a/vscode/package.json b/vscode/package.json
index 4ba273e2a971..7e37bcea24b7 100644
--- a/vscode/package.json
+++ b/vscode/package.json
@@ -32,15 +32,16 @@
     "watch:build:dev:desktop": "concurrently \"pnpm run -s _build:esbuild:desktop --watch\" \"pnpm run -s _build:webviews --mode development --watch\"",
     "_build:esbuild:desktop": "pnpm download-wasm && pnpm run -s _build:esbuild:uninstall && pnpm run -s _build:esbuild:node",
     "_build:esbuild:node": "esbuild ./src/extension.node.ts --bundle --outfile=dist/extension.node.js --external:vscode --external:typescript --alias:@sourcegraph/cody-shared=@sourcegraph/cody-shared/src/index --alias:@sourcegraph/cody-shared/src=@sourcegraph/cody-shared/src --alias:lexical=./build/lexical-package-fix --format=cjs --platform=node --sourcemap",
-    "_build:esbuild:web": "esbuild ./src/extension.web.ts --platform=browser --bundle --outfile=dist/extension.web.js --alias:@sourcegraph/cody-shared=@sourcegraph/cody-shared/src/index --alias:@sourcegraph/cody-shared/src=@sourcegraph/cody-shared/src --alias:path=path-browserify --external:typescript --alias:node:path=path-browserify --alias:node:os=os-browserify --external:vscode  --external:node:child_process  --external:node:util --external:node:fs --external:node:fs/promises --define:process='{\"env\":{}}' --define:window=self --format=cjs --sourcemap",
-    "_build:esbuild:uninstall": "esbuild ./src/uninstall/post-uninstall.ts --bundle --outfile=dist/post-uninstall.js --external:typescript --format=cjs --platform=node --sourcemap --alias:@sourcegraph/cody-shared=@sourcegraph/cody-shared/src/index --alias:@sourcegraph/cody-shared/src=@sourcegraph/cody-shared/src --alias:lexical=./build/lexical-package-fix",
+    "_build:esbuild:web": "esbuild ./src/extension.web.ts --platform=browser --bundle --outfile=dist/extension.web.js --alias:@sourcegraph/cody-shared=@sourcegraph/cody-shared/src/index --alias:@sourcegraph/cody-shared/src=@sourcegraph/cody-shared/src --alias:path=path-browserify --external:typescript --alias:node:path=path-browserify --alias:node:os=os-browserify --alias:os=os-browserify --external:vscode  --external:node:child_process  --external:node:util --external:node:fs --external:node:fs/promises --external:node:process --define:process='{\"env\":{}}' --define:window=self --format=cjs --sourcemap",
+    "_build:esbuild:uninstall": "node ./uninstall/esbuild.mjs",
     "_build:webviews": "vite -c webviews/vite.config.mts build",
+    "_build:vsix_for_test": "vsce package --no-dependencies --out dist/cody.e2e.vsix",
     "release": "ts-node-transpile-only ./scripts/release.ts",
     "download-wasm": "ts-node-transpile-only ./scripts/download-wasm-modules.ts",
     "copy-win-ca-roots": "ts-node-transpile-only ./scripts/copy-win-ca-roots.ts",
     "release:dry-run": "pnpm run download-wasm && CODY_RELEASE_DRY_RUN=1 ts-node ./scripts/release.ts",
     "storybook": "storybook dev -p 6007 --no-open --no-version-updates",
-    "test:e2e": "playwright install && tsc --build && node dist/tsc/test/e2e/install-deps.js && pnpm run -s build:dev:desktop && pnpm run -s test:e2e:run",
+    "test:e2e": "playwright install && tsc --build && node dist/tsc/test/e2e/install-deps.js && pnpm run -s _build:vsix_for_test && pnpm run -s build:dev:desktop && pnpm run -s test:e2e:run",
     "test:e2e:run": "playwright test",
     "test:e2e2": "pnpm -s test:e2e2:deps && pnpm -s build:root && pnpm -s build:dev:desktop && pnpm -s test:e2e2:run",
     "test:e2e2:run": "playwright test -c playwright.v2.config.ts",
@@ -1424,7 +1425,7 @@
     "@types/unzipper": "^0.10.7",
     "@types/uuid": "^9.0.2",
     "@types/vscode": "^1.79.0",
-    "@vscode/test-electron": "^2.3.8",
+    "@vscode/test-electron": "^2.4.0",
     "@vscode/test-web": "^0.0.47",
     "@vscode/vsce": "^2.22.0",
     "ajv": "^8.14.0",
diff --git a/vscode/src/configuration.ts b/vscode/src/configuration.ts
index 0c6c9ab537d1..d8cf9b649af9 100644
--- a/vscode/src/configuration.ts
+++ b/vscode/src/configuration.ts
@@ -172,5 +172,6 @@ export function setStaticResolvedConfigurationWithAuthCredentials({
         configuration: { ...getConfiguration(), customHeaders: configuration.customHeaders },
         auth,
         clientState: localStorage.getClientState(),
+        isReinstall: false,
     })
 }
diff --git a/vscode/src/extension.node.ts b/vscode/src/extension.node.ts
index 4c934b7c86ab..80a863b002f4 100644
--- a/vscode/src/extension.node.ts
+++ b/vscode/src/extension.node.ts
@@ -1,12 +1,7 @@
 // Sentry should be imported first
 import { NodeSentryService } from './services/sentry/sentry.node'
 
-import {
-    currentAuthStatus,
-    currentResolvedConfig,
-    resolvedConfig,
-    subscriptionDisposable,
-} from '@sourcegraph/cody-shared'
+import { resolvedConfig, subscriptionDisposable } from '@sourcegraph/cody-shared'
 import * as vscode from 'vscode'
 import { startTokenReceiver } from './auth/token-receiver'
 import { CommandsProvider } from './commands/services/provider'
@@ -16,9 +11,7 @@ import { type ExtensionClient, defaultVSCodeExtensionClient } from './extension-
 import { activate as activateCommon } from './extension.common'
 import { initializeNetworkAgent, setCustomAgent } from './fetch.node'
 import { SymfRunner } from './local-context/symf'
-import { localStorage } from './services/LocalStorageProvider'
 import { OpenTelemetryService } from './services/open-telemetry/OpenTelemetryService.node'
-import { serializeConfigSnapshot } from './uninstall/serializeConfig'
 
 /**
  * Activation entrypoint for the VS Code extension when running VS Code as a desktop app
@@ -59,15 +52,3 @@ export function activate(
         extensionClient,
     })
 }
-
-// When Cody is deactivated, we serialize the current configuration to disk,
-// so that it can be sent with Telemetry when the post-uninstall script runs.
-// The vscode API is not available in the post-uninstall script.
-export async function deactivate(): Promise<void> {
-    const config = localStorage.getConfig() ?? (await currentResolvedConfig())
-    const authStatus = currentAuthStatus()
-    serializeConfigSnapshot({
-        config,
-        authStatus,
-    })
-}
diff --git a/vscode/src/jsonrpc/agent-protocol.ts b/vscode/src/jsonrpc/agent-protocol.ts
index 3e8cf9855a94..b5fabbfb24ae 100644
--- a/vscode/src/jsonrpc/agent-protocol.ts
+++ b/vscode/src/jsonrpc/agent-protocol.ts
@@ -284,6 +284,10 @@ export type ClientRequests = {
     // which match the specified regular expressions. Pass `undefined` to remove
     // the override.
     'testing/ignore/overridePolicy': [ContextFilters | null, null]
+
+    // Called after the extension has been uninstalled by a user action.
+    // Attempts to wipe out any state that the extension has stored.
+    'extension/reset': [null, null]
 }
 
 // ================
diff --git a/vscode/src/main.ts b/vscode/src/main.ts
index 7176d3cafe00..16bbc2380703 100644
--- a/vscode/src/main.ts
+++ b/vscode/src/main.ts
@@ -4,6 +4,7 @@ import {
     type ChatClient,
     ClientConfigSingleton,
     type ConfigurationInput,
+    DOTCOM_URL,
     type DefaultCodyCommands,
     FeatureFlag,
     type Guardrails,
@@ -36,8 +37,10 @@ import {
     take,
     telemetryRecorder,
 } from '@sourcegraph/cody-shared'
+import _ from 'lodash'
 import { isEqual } from 'lodash'
 import { filter, map } from 'observable-fns'
+import { isReinstalling } from '../uninstall/reinstall'
 import type { CommandResult } from './CommandResult'
 import { showAccountMenu } from './auth/account-menu'
 import { showSignInMenu, showSignOutMenu, tokenCallbackHandler } from './auth/auth'
@@ -135,6 +138,8 @@ export async function start(
         agentCapabilities: platform.extensionClient.capabilities,
     })
 
+    let hasReinstallCleanupRun = false
+
     setResolvedConfigurationObservable(
         combineLatest(
             fromVSCodeEvent(vscode.workspace.onDidChangeConfiguration).pipe(
@@ -157,6 +162,30 @@ export async function start(
                         clientConfiguration,
                         clientSecrets,
                         clientState,
+                        reinstall: {
+                            isReinstalling,
+                            onReinstall: async () => {
+                                // short circuit so that we only run this cleanup once, not every time the config updates
+                                if (hasReinstallCleanupRun) return
+                                logDebug('start', 'Reinstalling Cody')
+                                // VSCode does not provide a way to simply clear all secrets
+                                // associated with the extension (https://github.com/microsoft/vscode/issues/123817)
+                                // So we have to build a list of all endpoints we'd expect to have been populated
+                                // and clear them individually.
+                                const history = await localStorage.deleteEndpointHistory()
+                                const additionalEndpointsToClear = [
+                                    clientConfiguration.overrideServerEndpoint,
+                                    clientState.lastUsedEndpoint,
+                                    DOTCOM_URL.toString(),
+                                ].filter(_.isString)
+                                await Promise.all(
+                                    history
+                                        .concat(additionalEndpointsToClear)
+                                        .map(clientSecrets.deleteToken.bind(clientSecrets))
+                                )
+                                hasReinstallCleanupRun = true
+                            },
+                        },
                     }) satisfies ConfigurationInput
             )
         )
diff --git a/vscode/src/services/AuthProvider.test.ts b/vscode/src/services/AuthProvider.test.ts
index 7964d4341553..2ff7fd5a7ab0 100644
--- a/vscode/src/services/AuthProvider.test.ts
+++ b/vscode/src/services/AuthProvider.test.ts
@@ -149,6 +149,10 @@ describe('AuthProvider', () => {
             .mockReturnValue(asyncValue(authedAuthStatusAlice, 10))
 
         const { authProvider, authStatus, resolvedConfig } = setup()
+        const mockSerializeUninstallerInfo = vi
+            .spyOn(authProvider, 'serializeUninstallerInfo')
+            .mockReturnValue(asyncValue(undefined, 10))
+
         const { values, clearValues } = readValuesFrom(authStatus)
         resolvedConfig.next({
             configuration: {},
@@ -165,6 +169,7 @@ describe('AuthProvider', () => {
         clearValues()
         expect(validateCredentialsMock).toHaveBeenCalledTimes(1)
         expect(saveEndpointAndTokenMock).toHaveBeenCalledTimes(0)
+        expect(mockSerializeUninstallerInfo).toHaveBeenCalledTimes(0)
 
         // Call validateAndStoreCredentials.
         validateCredentialsMock.mockReturnValue(asyncValue(authedAuthStatusBob, 10))
@@ -180,12 +185,14 @@ describe('AuthProvider', () => {
         expect(values).toStrictEqual<typeof values>([])
         expect(validateCredentialsMock).toHaveBeenCalledTimes(2)
         expect(saveEndpointAndTokenMock).toHaveBeenCalledTimes(0)
+        expect(mockSerializeUninstallerInfo).toHaveBeenCalledTimes(0)
 
         await vi.advanceTimersByTimeAsync(9)
         await promise
         expect(values).toStrictEqual<typeof values>([authedAuthStatusBob])
         expect(validateCredentialsMock).toHaveBeenCalledTimes(2)
         expect(saveEndpointAndTokenMock).toHaveBeenCalledTimes(1)
+        expect(mockSerializeUninstallerInfo).toHaveBeenCalledTimes(1)
     })
 
     test('refresh', async () => {
diff --git a/vscode/src/services/AuthProvider.ts b/vscode/src/services/AuthProvider.ts
index d9b00a237b01..766f988f6e65 100644
--- a/vscode/src/services/AuthProvider.ts
+++ b/vscode/src/services/AuthProvider.ts
@@ -3,16 +3,17 @@ import * as vscode from 'vscode'
 import {
     type AuthCredentials,
     type AuthStatus,
+    type ClientCapabilitiesWithLegacyFields,
     NEVER,
     type ResolvedConfiguration,
     type Unsubscribable,
     abortableOperation,
     authStatus,
-    clientCapabilities,
     combineLatest,
     currentResolvedConfig,
     disposableSubscription,
     distinctUntilChanged,
+    clientCapabilities as getClientCapabilities,
     isAbortError,
     normalizeServerEndpointURL,
     pluck,
@@ -25,9 +26,11 @@ import {
 } from '@sourcegraph/cody-shared'
 import isEqual from 'lodash/isEqual'
 import { Observable, Subject } from 'observable-fns'
+import { serializeConfigSnapshot } from '../../uninstall/serializeConfig'
 import { type ResolvedConfigurationCredentialsOnly, validateCredentials } from '../auth/auth'
 import { logError } from '../output-channel-logger'
 import { maybeStartInteractiveTutorial } from '../tutorial/helpers'
+import { version } from '../version'
 import { localStorage } from './LocalStorageProvider'
 
 const HAS_AUTHENTICATED_BEFORE_KEY = 'has-authenticated-before'
@@ -70,7 +73,7 @@ class AuthProvider implements vscode.Disposable {
             )
                 .pipe(
                     abortableOperation(async ([config], signal) => {
-                        if (clientCapabilities().isCodyWeb) {
+                        if (getClientCapabilities().isCodyWeb) {
                             // Cody Web calls {@link AuthProvider.validateAndStoreCredentials}
                             // explicitly. This early exit prevents duplicate authentications during
                             // the initial load.
@@ -176,7 +179,10 @@ class AuthProvider implements vscode.Disposable {
         const shouldStore = mode === 'always-store' || authStatus.authenticated
         if (shouldStore) {
             this.lastValidatedAndStoredCredentials.next(credentials)
-            await localStorage.saveEndpointAndToken(credentials.auth)
+            await Promise.all([
+                localStorage.saveEndpointAndToken(credentials.auth),
+                this.serializeUninstallerInfo(authStatus),
+            ])
             this.status.next(authStatus)
             signal?.throwIfAborted()
         }
@@ -212,6 +218,34 @@ class AuthProvider implements vscode.Disposable {
     private setHasAuthenticatedBefore() {
         return localStorage.set(HAS_AUTHENTICATED_BEFORE_KEY, 'true')
     }
+
+    // When the auth status is updated, we serialize the current configuration to disk,
+    // so that it can be sent with Telemetry when the post-uninstall script runs.
+    // we only write on auth change as that is the only significantly important factor
+    // and we don't want to write too frequently (so we don't react to config changes)
+    // The vscode API is not available in the post-uninstall script.
+    // Public so that it can be mocked for testing
+    public async serializeUninstallerInfo(authStatus: AuthStatus): Promise<void> {
+        if (!authStatus.authenticated) return
+        let clientCapabilities: ClientCapabilitiesWithLegacyFields | undefined
+        try {
+            clientCapabilities = getClientCapabilities()
+        } catch {
+            // If client capabilities cannot be retrieved, we will just synthesize
+            // them from defaults in the post-uninstall script.
+        }
+        // TODO: put this behind a proper client capability if any other IDE's need to uninstall
+        // the same way as VSCode (most editors have a proper uninstall hook)
+        if (clientCapabilities?.isVSCode) {
+            const config = localStorage.getConfig() ?? (await currentResolvedConfig())
+            await serializeConfigSnapshot({
+                config,
+                authStatus,
+                clientCapabilities,
+                version,
+            })
+        }
+    }
 }
 
 export const authProvider = new AuthProvider()
diff --git a/vscode/src/services/LocalStorageProvider.ts b/vscode/src/services/LocalStorageProvider.ts
index f0b8b76b39ea..9338d7d15d56 100644
--- a/vscode/src/services/LocalStorageProvider.ts
+++ b/vscode/src/services/LocalStorageProvider.ts
@@ -139,6 +139,13 @@ class LocalStorage implements LocalStorageForModelPreferences {
         await this.set(this.LAST_USED_ENDPOINT, null)
     }
 
+    // Deletes and returns the endpoint history
+    public async deleteEndpointHistory(): Promise<string[]> {
+        const history = this.getEndpointHistory()
+        await Promise.all([this.deleteEndpoint(), this.set(this.CODY_ENDPOINT_HISTORY, null)])
+        return history || []
+    }
+
     public getEndpointHistory(): string[] | null {
         return this.get<string[] | null>(this.CODY_ENDPOINT_HISTORY)
     }
diff --git a/vscode/src/services/telemetry-v2.ts b/vscode/src/services/telemetry-v2.ts
index 6760d7e829be..a7cb9e8ec771 100644
--- a/vscode/src/services/telemetry-v2.ts
+++ b/vscode/src/services/telemetry-v2.ts
@@ -44,7 +44,7 @@ export function createOrUpdateTelemetryRecorderProvider(
     isExtensionModeDevOrTest: boolean
 ): Disposable {
     return subscriptionDisposable(
-        resolvedConfig.subscribe(({ configuration, auth, clientState }) => {
+        resolvedConfig.subscribe(({ configuration, auth, clientState, isReinstall }) => {
             // Add timestamp processor for realistic data in output for dev or no-op scenarios
             const defaultNoOpProvider = new NoOpTelemetryRecorderProvider([
                 new TimestampTelemetryProcessor(),
@@ -86,16 +86,20 @@ export function createOrUpdateTelemetryRecorderProvider(
              */
             const newAnonymousUser = localStorage.checkIfCreatedAnonymousUserID()
             if (initialize && !clientCapabilities().isCodyWeb) {
-                if (newAnonymousUser) {
+                if (newAnonymousUser || isReinstall) {
                     /**
                      * New user
                      */
-                    telemetryRecorder.recordEvent('cody.extension', 'installed', {
-                        billingMetadata: {
-                            product: 'cody',
-                            category: 'billable',
-                        },
-                    })
+                    telemetryRecorder.recordEvent(
+                        'cody.extension',
+                        isReinstall ? 'reinstalled' : 'installed',
+                        {
+                            billingMetadata: {
+                                product: 'cody',
+                                category: 'billable',
+                            },
+                        }
+                    )
                 } else if (
                     !configuration.isRunningInsideAgent ||
                     configuration.agentHasPersistentStorage
diff --git a/vscode/src/uninstall/post-uninstall.ts b/vscode/src/uninstall/post-uninstall.ts
deleted file mode 100644
index 71fb4b9e1d78..000000000000
--- a/vscode/src/uninstall/post-uninstall.ts
+++ /dev/null
@@ -1,44 +0,0 @@
-import {
-    TelemetryRecorderProvider,
-    nextTick,
-    setAuthStatusObservable,
-    setStaticResolvedConfigurationValue,
-} from '@sourcegraph/cody-shared'
-import { Observable } from 'observable-fns'
-import { deleteUninstallerDirectory, readConfig } from './serializeConfig'
-
-async function main() {
-    // Do not record telemetry events during testing
-    if (process.env.CODY_TESTING) {
-        return
-    }
-
-    const uninstaller = readConfig()
-    if (uninstaller) {
-        const { config, authStatus } = uninstaller
-        if (config && authStatus) {
-            try {
-                setStaticResolvedConfigurationValue(config)
-            } catch {}
-            try {
-                setAuthStatusObservable(Observable.of(authStatus))
-            } catch {}
-            // Wait for `currentAuthStatusOrNotReadyYet` to have this value synchronously.
-            await nextTick()
-
-            const provider = new TelemetryRecorderProvider(config, 'connected-instance-only')
-            const recorder = provider.getRecorder()
-            recorder.recordEvent('cody.extension', 'uninstalled', {
-                billingMetadata: {
-                    product: 'cody',
-                    category: 'billable',
-                },
-            })
-
-            // cleanup the uninstaller config
-            deleteUninstallerDirectory()
-        }
-    }
-}
-
-main()
diff --git a/vscode/src/uninstall/serializeConfig.ts b/vscode/src/uninstall/serializeConfig.ts
deleted file mode 100644
index ddbba402cb7a..000000000000
--- a/vscode/src/uninstall/serializeConfig.ts
+++ /dev/null
@@ -1,66 +0,0 @@
-import * as fs from 'node:fs'
-import * as os from 'node:os'
-import * as path from 'node:path'
-import type { AuthStatus, ResolvedConfiguration } from '@sourcegraph/cody-shared'
-
-import { Platform, getOSArch } from '../os'
-
-const CONFIG_FILE = 'config.json'
-
-function getPlatformSpecificDirectory(): string {
-    const { platform } = getOSArch()
-    const appName = 'cody-ai'
-
-    switch (platform) {
-        case Platform.Windows:
-            return path.join(process.env.APPDATA || os.homedir(), appName)
-        case Platform.Mac:
-        case Platform.Linux:
-            return path.join(os.homedir(), '.config', appName)
-        default:
-            throw new Error(`Unsupported platform: ${platform}`)
-    }
-}
-
-function ensureDirectoryExists(directory: string) {
-    if (!fs.existsSync(directory)) {
-        fs.mkdirSync(directory, { recursive: true })
-    }
-}
-
-// Used to cleanup the uninstaller directory after the last telemetry event is sent
-export function deleteUninstallerDirectory() {
-    fs.rmdirSync(getPlatformSpecificDirectory(), { recursive: true })
-}
-
-function writeSnapshot(directory: string, filename: string, content: any) {
-    const filePath = path.join(directory, filename)
-
-    fs.writeFileSync(filePath, JSON.stringify(content, null, 2))
-}
-
-interface UninstallerConfig {
-    config?: ResolvedConfiguration
-    authStatus: AuthStatus | undefined
-}
-
-/**
- * Serializes the current configuration and auth status to disk. This is used in the case
- * of an uninstall event to log one last telemetry event.
- */
-export function serializeConfigSnapshot(uninstall: UninstallerConfig) {
-    const directory = getPlatformSpecificDirectory()
-    ensureDirectoryExists(directory)
-    writeSnapshot(directory, CONFIG_FILE, uninstall)
-}
-
-export function readConfig(): UninstallerConfig | null {
-    const file = path.join(getPlatformSpecificDirectory(), CONFIG_FILE)
-
-    if (!fs.existsSync(file)) {
-        return null
-    }
-
-    const obj = fs.readFileSync(file, 'utf-8')
-    return JSON.parse(obj)
-}
diff --git a/vscode/test/e2e/helpers.ts b/vscode/test/e2e/helpers.ts
index ab09b519272a..70c571a8286f 100644
--- a/vscode/test/e2e/helpers.ts
+++ b/vscode/test/e2e/helpers.ts
@@ -27,6 +27,7 @@ import {
 
 import type { RepoListResponse } from '@sourcegraph/cody-shared'
 import type { RepositoryIdResponse } from '@sourcegraph/cody-shared/src/sourcegraph-api/graphql/client'
+import { resolveCliArgsFromVSCodeExecutablePath } from '@vscode/test-electron'
 import { closeSidebar, expectAuthenticated, focusSidebar } from './common'
 import { installVsCode } from './install-deps'
 import { buildCustomCommandConfigFile } from './utils/buildCustomCommands'
@@ -73,6 +74,17 @@ export const getAssetsDir = (testName: string): string =>
 export const testAssetsTmpDir = (testName: string, label: string): string =>
     path.join(getAssetsDir(testName), `temp-${label}`)
 
+export interface OpenVSCodeOptions {
+    // A list of extensions to install or uninstall before starting VSCode. These can
+    // be extensions that are already published to the VSCode Marketplace, or they can
+    // be local paths to a VSIX package. Useful if you want to behavior related to setup / teardown
+    installExtensions?: string[]
+    uninstallExtensions?: string[]
+    // Whether or not the code in the current git tree will be installed int the VSCode
+    // instance. Defaults to true.
+    skipLocalInstall?: boolean
+}
+
 export const test = base
     // By default, use ../../test/fixtures/workspace as the workspace.
     .extend<WorkspaceDirectory>({
@@ -137,9 +149,9 @@ export const test = base
             { auto: true },
         ],
     })
-    .extend<{ app: ElectronApplication }>({
+    .extend<{ openVSCode: (opts?: OpenVSCodeOptions) => Promise<ElectronApplication> }>({
         // starts a new instance of vscode with the given workspace settings
-        app: async (
+        openVSCode: async (
             {
                 workspaceDirectory,
                 extraWorkspaceSettings,
@@ -174,37 +186,70 @@ export const test = base
                     TESTING_SECRET_STORAGE_TOKEN: JSON.stringify([SERVER_URL, VALID_TOKEN]),
                 }
             }
+            const args = [
+                // https://github.com/microsoft/vscode/issues/84238
+                '--no-sandbox',
+                // https://github.com/microsoft/vscode-test/issues/120
+                '--disable-updates',
+                '--skip-welcome',
+                '--skip-release-notes',
+                '--disable-workspace-trust',
+                `--user-data-dir=${userDataDirectory}`,
+                `--extensions-dir=${extensionsDirectory}`,
+            ]
+
+            async function runVSCodeCommand(cmd: string): Promise<void> {
+                const [cli, ...additionalArgs] =
+                    resolveCliArgsFromVSCodeExecutablePath(vscodeExecutablePath)
+
+                await spawn(cli, [...additionalArgs, ...args, cmd], {
+                    stdio: 'ignore',
+                    shell: process.platform === 'win32',
+                })
+            }
+
             // See: https://github.com/microsoft/vscode-test/blob/main/lib/runTest.ts
-            const app = await electron.launch({
-                executablePath: vscodeExecutablePath,
-                env: {
-                    ...process.env,
-                    ...dotcomUrlOverride,
-                    ...secretStorageState,
-                    CODY_TESTING: 'true',
-                    CODY_LOG_FILE: tmpLogFile,
-                },
-                args: [
-                    // https://github.com/microsoft/vscode/issues/84238
-                    '--no-sandbox',
-                    // https://github.com/microsoft/vscode-test/issues/120
-                    '--disable-updates',
-                    '--skip-welcome',
-                    '--skip-release-notes',
-                    '--disable-workspace-trust',
-                    `--extensionDevelopmentPath=${extensionDevelopmentPath}`,
-                    `--user-data-dir=${userDataDirectory}`,
-                    `--extensions-dir=${extensionsDirectory}`,
-                    workspaceDirectory,
-                ],
-                recordVideo: {
-                    // All running tests will be recorded to a temp video file.
-                    // successful runs will be deleted, failures will be kept
-                    dir: testAssetsTmpDir(testInfo.title, 'videos'),
-                },
-            })
+            use(async (opts: OpenVSCodeOptions = {}) => {
+                if (opts.installExtensions?.length) {
+                    runVSCodeCommand(
+                        opts.installExtensions.map(ext => `--install-extension=${ext}`).join(' ')
+                    )
+                }
+                if (opts.uninstallExtensions?.length) {
+                    runVSCodeCommand(
+                        opts.uninstallExtensions.map(ext => `--uninstall-extension=${ext}`).join(' ')
+                    )
+                }
+                if (!opts.skipLocalInstall) {
+                    args.push(`--extensionDevelopmentPath=${extensionDevelopmentPath}`)
+                }
+
+                args.push(workspaceDirectory)
 
-            await waitUntil(() => app.windows().length > 0)
+                const app = await electron.launch({
+                    executablePath: vscodeExecutablePath,
+                    env: {
+                        ...process.env,
+                        ...dotcomUrlOverride,
+                        ...secretStorageState,
+                        CODY_TESTING: 'true',
+                        CODY_LOG_FILE: tmpLogFile,
+                    },
+                    args,
+                    recordVideo: {
+                        // All running tests will be recorded to a temp video file.
+                        // successful runs will be deleted, failures will be kept
+                        dir: testAssetsTmpDir(testInfo.title, 'videos'),
+                    },
+                })
+                await waitUntil(() => app.windows().length > 0)
+                return app
+            })
+        },
+    })
+    .extend<{ app: ElectronApplication }>({
+        app: async ({ openVSCode, userDataDirectory, extensionsDirectory }, use) => {
+            const app = await openVSCode()
 
             await use(app)
 
@@ -337,7 +382,7 @@ export async function rmSyncWithRetries(path: PathLike, options?: RmOptions): Pr
     }
 }
 
-async function getCodySidebar(page: Page): Promise<Frame> {
+export async function getCodySidebar(page: Page): Promise<Frame> {
     async function findCodySidebarFrame(): Promise<null | Frame> {
         for (const frame of page.frames()) {
             try {
@@ -347,9 +392,13 @@ async function getCodySidebar(page: Page): Promise<Frame> {
                 }
             } catch (error: any) {
                 // Skip over frames that were detached in the meantime.
-                if (error.message.indexOf('Frame was detached') === -1) {
-                    throw error
+                if (
+                    error.message.includes('Frame was detached') ||
+                    error.message.includes('because of a navigation')
+                ) {
+                    continue
                 }
+                throw error
             }
         }
         return null
@@ -412,7 +461,7 @@ export async function executeCommandInPalette(page: Page, commandName: string):
 /**
  * Verifies that loggedEvents contain all of expectedEvents (in any order).
  */
-const expect = baseExpect.extend({
+export const expect = baseExpect.extend({
     async toContainEvents(
         received: string[],
         expected: string[],
@@ -424,11 +473,9 @@ const expect = baseExpect.extend({
 
         try {
             await baseExpect
-                .poll(() => received, { timeout: 3000, ...options })
+                .poll(() => received, { timeout: options?.timeout ?? 3000, ...options })
                 .toEqual(baseExpect.arrayContaining(expected))
         } catch (e: any) {
-            // const missingEvents = new Set()
-            // const extraEvents = new Set()
             const receivedSet = new Set(received)
             for (const event of expected) {
                 if (!receivedSet.has(event)) {
diff --git a/vscode/test/e2e/install-deps.ts b/vscode/test/e2e/install-deps.ts
index e6f7a08ada06..3f6980a05ed1 100644
--- a/vscode/test/e2e/install-deps.ts
+++ b/vscode/test/e2e/install-deps.ts
@@ -1,12 +1,6 @@
 import { spawn } from 'node:child_process'
 
-import {
-    ConsoleReporter,
-    type ProgressReport,
-    ProgressReportStage,
-    downloadAndUnzipVSCode as _downloadAndUnzipVSCode,
-} from '@vscode/test-electron'
-import type { DownloadOptions } from '@vscode/test-electron/out/download'
+import { SilentReporter, downloadAndUnzipVSCode } from '@vscode/test-electron'
 
 // The VS Code version to use for e2e tests (there is also a version in ../integration/main.ts used for integration tests).
 //
@@ -15,38 +9,8 @@ import type { DownloadOptions } from '@vscode/test-electron/out/download'
 // missed because we're running on an older version than users.
 const vscodeVersion = 'stable'
 
-// A custom version of the VS Code download reporter that silences matching installation
-// notifications as these otherwise are emitted on every test run
-class CustomConsoleReporter extends ConsoleReporter {
-    public report(report: ProgressReport): void {
-        if (report.stage !== ProgressReportStage.FoundMatchingInstall) {
-            super.report(report)
-        }
-    }
-}
-
-/**
- * Patches the default logger but otherwise leaves all options available
- * @param opts
- */
-export function downloadAndUnzipVSCode(opts: Partial<DownloadOptions>) {
-    return _downloadAndUnzipVSCode(
-        Object.assign(
-            {
-                version: vscodeVersion,
-                reporter: new CustomConsoleReporter(process.stdout.isTTY),
-            } satisfies Partial<DownloadOptions>,
-            opts
-        )
-    )
-}
-
-export function installVsCode(): Promise<string> {
-    return _downloadAndUnzipVSCode(
-        vscodeVersion,
-        undefined,
-        new CustomConsoleReporter(process.stdout.isTTY)
-    )
+export async function installVsCode(): Promise<string> {
+    return downloadAndUnzipVSCode(vscodeVersion, undefined, new SilentReporter())
 }
 
 function installChromium(): Promise<void> {
diff --git a/vscode/test/e2e/uninstall.test.ts b/vscode/test/e2e/uninstall.test.ts
new file mode 100644
index 000000000000..b04fe37938b6
--- /dev/null
+++ b/vscode/test/e2e/uninstall.test.ts
@@ -0,0 +1,56 @@
+import path from 'node:path'
+import type { Page } from 'playwright'
+import { loggedV2Events } from '../fixtures/mock-server'
+import { expectAuthenticated, focusSidebar, sidebarSignin } from './common'
+import { expect, getCodySidebar, test } from './helpers'
+
+test('uninstall extension', async ({ openVSCode }) => {
+    // In order to trigger the uninstall event, we need to actually install the extension
+    // into the local vscode instance
+    const customExtensionVSIX = path.join(process.cwd(), 'dist', 'cody.e2e.vsix')
+    let app = await openVSCode({
+        installExtensions: [customExtensionVSIX],
+        skipLocalInstall: true,
+    })
+    let page = await app.firstWindow()
+    await signin(page)
+    await app.close()
+
+    // Now we uninstall the extension, and re-open VSCode. This will trigger the
+    // vscode:uninstall event which will trigger telemetry events and set a marker
+    // that the app has been uninstalled
+    app = await openVSCode({
+        uninstallExtensions: [customExtensionVSIX],
+        skipLocalInstall: true,
+    })
+    // Allow the uninstaller to finish
+    await expect(loggedV2Events).toContainEvents(['cody.extension:uninstalled'], { timeout: 5000 })
+    await app.close()
+
+    // we re-install the extension, and re-open VSCode. This will trigger the
+    // the reinstall flow which will trigger telemetry events but will clear out secret storage
+    app = await openVSCode({
+        installExtensions: [customExtensionVSIX],
+        skipLocalInstall: true,
+    })
+    page = await app.firstWindow()
+
+    // This will fail if the credentials are saved because the login screen will still be
+    // visible, thus it acts as an implicit test that credentials were cleared out
+    await signin(page)
+    await expect(loggedV2Events).toContainEvents(['cody.extension:reinstalled'], { timeout: 5000 })
+    await app.close()
+
+    // Finally, re-open the VSCode and ensure that we are still logged in
+    app = await openVSCode({
+        skipLocalInstall: true,
+    })
+    page = await app.firstWindow()
+    await expectAuthenticated(page)
+})
+
+async function signin(page: Page): Promise<void> {
+    await focusSidebar(page)
+    const sidebar = await getCodySidebar(page)
+    await sidebarSignin(page, sidebar)
+}
diff --git a/vscode/tsconfig.json b/vscode/tsconfig.json
index f83c0a08f846..ea82d5d5fba9 100644
--- a/vscode/tsconfig.json
+++ b/vscode/tsconfig.json
@@ -22,7 +22,8 @@
     "e2e",
     "webviews",
     "webviews/*.d.ts",
-    "package.json"
+    "package.json",
+    "uninstall"
   ],
   "exclude": [
     "typehacks",
diff --git a/vscode/uninstall/esbuild.mjs b/vscode/uninstall/esbuild.mjs
new file mode 100644
index 000000000000..e2c3b2200378
--- /dev/null
+++ b/vscode/uninstall/esbuild.mjs
@@ -0,0 +1,39 @@
+// @ts-ignore this is not compiled by typescript so it can import files from outside the rootDir
+import { detectForbiddenImportPlugin } from '../../lib/shared/esbuild.utils.mjs'
+
+import { build as esbuild } from 'esbuild'
+
+async function build() {
+    const plugins = [detectForbiddenImportPlugin(['vscode'])]
+    /** @type {import('esbuild').BuildOptions} */
+    const esbuildOptions = {
+        entryPoints: ['./uninstall/post-uninstall.ts'],
+        bundle: true,
+        platform: 'node',
+        sourcemap: true,
+        logLevel: 'silent',
+        write: true,
+        outfile: './dist/post-uninstall.js',
+        plugins,
+        external: ['typescript'],
+        format: 'cjs',
+        alias: {
+            // Build from TypeScript sources so we don't need to run `tsc -b` in the background
+            // during dev.
+            '@sourcegraph/cody-shared': '@sourcegraph/cody-shared/src/index',
+            '@sourcegraph/cody-shared/src': '@sourcegraph/cody-shared/src',
+            lexical: './build/lexical-package-fix',
+        },
+    }
+
+    return esbuild(esbuildOptions)
+}
+
+build()
+    .then(() => {
+        console.log('Post-uninstall script built successfully.')
+    })
+    .catch(err => {
+        console.error('Could not build the post-uninstall script.', err.message)
+        process.exit(1)
+    })
diff --git a/vscode/uninstall/post-uninstall.ts b/vscode/uninstall/post-uninstall.ts
new file mode 100644
index 000000000000..e94cfc30a329
--- /dev/null
+++ b/vscode/uninstall/post-uninstall.ts
@@ -0,0 +1,61 @@
+import {
+    CodyIDE,
+    MockServerTelemetryRecorderProvider,
+    TelemetryRecorderProvider,
+    mockClientCapabilities,
+    nextTick,
+    setAuthStatusObservable,
+    setStaticResolvedConfigurationValue,
+} from '@sourcegraph/cody-shared'
+import { Observable } from 'observable-fns'
+import { createUninstallMarker } from './reinstall'
+import { deleteUninstallerConfig, readConfig } from './serializeConfig'
+
+async function main() {
+    const uninstaller = await readConfig()
+    if (uninstaller) {
+        const { config, authStatus, version, clientCapabilities } = uninstaller
+        if (config && authStatus) {
+            try {
+                setStaticResolvedConfigurationValue(config)
+            } catch (error) {
+                console.error('Failed to set config', error)
+            }
+            try {
+                setAuthStatusObservable(Observable.of(authStatus))
+            } catch (error) {
+                console.error('Failed to set auth status', error)
+            }
+            // Wait for `currentAuthStatusOrNotReadyYet` to have this value synchronously.
+            await nextTick()
+            mockClientCapabilities(
+                clientCapabilities ?? {
+                    agentIDE: CodyIDE.VSCode,
+                    isVSCode: true,
+                    isCodyWeb: false,
+                    agentExtensionVersion: version,
+                    // Unused by TelemetryRecorderProvider
+                    agentIDEVersion: '',
+                    telemetryClientName: `${CodyIDE.VSCode}.Cody`,
+                }
+            )
+
+            const provider = process.env.CODY_TESTING
+                ? new MockServerTelemetryRecorderProvider(config)
+                : new TelemetryRecorderProvider(config, 'connected-instance-only')
+            const recorder = provider.getRecorder()
+            recorder.recordEvent('cody.extension', 'uninstalled', {
+                billingMetadata: {
+                    product: 'cody',
+                    category: 'billable',
+                },
+            })
+
+            // cleanup the uninstaller config
+            await deleteUninstallerConfig()
+            await createUninstallMarker()
+        }
+    }
+}
+
+main()
diff --git a/vscode/uninstall/reinstall.ts b/vscode/uninstall/reinstall.ts
new file mode 100644
index 000000000000..c69c3d2425e6
--- /dev/null
+++ b/vscode/uninstall/reinstall.ts
@@ -0,0 +1,29 @@
+import fs from 'node:fs/promises'
+import path from 'node:path'
+import { codyPaths } from '@sourcegraph/cody-shared'
+
+export const uninstallMarker = path.join(codyPaths().config, 'uninstall-marker')
+
+export const createUninstallMarker = async (): Promise<void> => {
+    await fs.writeFile(uninstallMarker, '')
+}
+
+let isReinstall: boolean | undefined = undefined
+// Checks if the user is reinstalling the extension by checking for the existence of a marker file
+// If found, it deletes the marker file so that we only report reinstalling once
+// Caches the value of isReinstall so that throughout the lifetime of the extension
+// it still reports it as a re-install
+export const isReinstalling = async (): Promise<boolean> => {
+    if (typeof isReinstall === 'boolean') {
+        return isReinstall
+    }
+    try {
+        await fs.stat(uninstallMarker)
+        await fs.unlink(uninstallMarker)
+        isReinstall = true
+    } catch (error) {
+        isReinstall = false
+    }
+
+    return isReinstall
+}
diff --git a/vscode/uninstall/serializeConfig.ts b/vscode/uninstall/serializeConfig.ts
new file mode 100644
index 000000000000..03d4f8497529
--- /dev/null
+++ b/vscode/uninstall/serializeConfig.ts
@@ -0,0 +1,70 @@
+import * as fs from 'node:fs/promises'
+import * as path from 'node:path'
+import {
+    type AuthStatus,
+    type ClientCapabilitiesWithLegacyFields,
+    type ResolvedConfiguration,
+    codyPaths,
+} from '@sourcegraph/cody-shared'
+
+const CONFIG_FILE = 'config.json'
+
+const getConfigPath = () => path.join(codyPaths().config, CONFIG_FILE)
+
+async function exists(path: string): Promise<boolean> {
+    try {
+        await fs.stat(path)
+        return true
+    } catch {
+        return false
+    }
+}
+
+async function ensureDirectoryExists(directory: string) {
+    if (!(await exists(directory))) {
+        await fs.mkdir(directory, { recursive: true })
+    }
+}
+
+// Used to cleanup the uninstaller directory after the last telemetry event is sent
+export async function deleteUninstallerConfig() {
+    return fs.rm(getConfigPath())
+}
+
+async function writeSnapshot(
+    directory: string,
+    filename: string,
+    content: UninstallerConfig
+): Promise<void> {
+    const filePath = path.join(directory, filename)
+
+    return fs.writeFile(filePath, JSON.stringify(content, null, 2))
+}
+
+interface UninstallerConfig {
+    config?: ResolvedConfiguration
+    authStatus: AuthStatus | undefined
+    clientCapabilities?: ClientCapabilitiesWithLegacyFields
+    version?: string
+}
+
+/**
+ * Serializes the current configuration and auth status to disk. This is used in the case
+ * of an uninstall event to log one last telemetry event.
+ */
+export async function serializeConfigSnapshot(uninstall: UninstallerConfig) {
+    const directory = codyPaths().config
+    await ensureDirectoryExists(directory)
+    await writeSnapshot(directory, CONFIG_FILE, uninstall)
+}
+
+export async function readConfig(): Promise<UninstallerConfig | null> {
+    const file = getConfigPath()
+
+    if (!(await exists(file))) {
+        return null
+    }
+
+    const obj = await fs.readFile(file, 'utf-8')
+    return JSON.parse(obj)
+}