diff --git a/packages/pyright-scip/src/virtualenv/environment.ts b/packages/pyright-scip/src/virtualenv/environment.ts
index 802ba9f8d..60931214e 100644
--- a/packages/pyright-scip/src/virtualenv/environment.ts
+++ b/packages/pyright-scip/src/virtualenv/environment.ts
@@ -1,5 +1,6 @@
 import * as fs from 'fs';
 import * as child_process from 'child_process';
+import * as os from 'os';
 import PythonPackage from './PythonPackage';
 import PythonEnvironment from './PythonEnvironment';
 import { withStatus } from 'src/status';
@@ -28,16 +29,60 @@ let getPipCommand = () => {
     return pipCommand;
 };
 
+function spawnSyncWithRetry(command: string, args: string[]): child_process.SpawnSyncReturns<string> {
+    let maxBuffer = 1 * 1024 * 1024; // Start with 1MB (original default)
+    const maxMemory = os.totalmem() * 0.1; // Don't use more than 10% of total system memory
+
+    while (true) {
+        const result = child_process.spawnSync(command, args, {
+            encoding: 'utf8',
+            maxBuffer: maxBuffer,
+        });
+
+        const error = result.error as NodeJS.ErrnoException | null;
+        if (error && error.code === 'ENOBUFS') {
+            const nextBuffer = maxBuffer * 10;
+            if (nextBuffer > maxMemory) {
+                throw new Error(
+                    `Command output too large: final attempt maxBuffer ${(maxBuffer / 1024 / 1024).toFixed(
+                        1
+                    )}MB (total memory: ${(maxMemory / 1024 / 1024).toFixed(1)}MB)`
+                );
+            }
+            maxBuffer = nextBuffer;
+            continue; // Retry with larger buffer
+        }
+
+        return result;
+    }
+}
+
 function pipList(): PipInformation[] {
-    return JSON.parse(child_process.execSync(`${getPipCommand()} list --format=json`).toString()) as PipInformation[];
+    const result = spawnSyncWithRetry(getPipCommand(), ['list', '--format=json']);
+
+    if (result.status !== 0) {
+        throw new Error(`pip list failed with code ${result.status}: ${result.stderr}`);
+    }
+
+    return JSON.parse(result.stdout) as PipInformation[];
 }
 
+// pipBulkShow returns the results of 'pip show', one for each package.
+//
+// It doesn't cross-check if the length of the output matches that of the input.
 function pipBulkShow(names: string[]): string[] {
-    // TODO: This probably breaks with enough names. Should batch them into 512 or whatever the max for bash would be
-    return child_process
-        .execSync(`${getPipCommand()} show -f ${names.join(' ')}`)
-        .toString()
-        .split('\n---');
+    // FIXME: The performance of this scales with the number of packages that
+    // are installed in the Python distribution, not just the number of packages
+    // that are requested. If 10K packages are installed, this can take several
+    // minutes. However, it's not super obvious if there is a more performant
+    // way to do this without hand-rolling the functionality ourselves.
+    const result = spawnSyncWithRetry(getPipCommand(), ['show', '-f', ...names]);
+
+    if (result.status !== 0) {
+        throw new Error(`pip show failed with code ${result.status}: ${result.stderr}`);
+    }
+
+    return result.stdout.split('\n---').filter((pkg) => pkg.trim());
 }
 
 export default function getEnvironment(