diff --git a/src/unixTerminal.ts b/src/unixTerminal.ts
index 526adcd5e..44a3383dc 100644
--- a/src/unixTerminal.ts
+++ b/src/unixTerminal.ts
@@ -12,8 +12,14 @@ import { assign } from './utils';
 let pty: IUnixNative;
 try {
   pty = require('../build/Release/pty.node');
-} catch {
-  pty = require('../build/Debug/pty.node');
+} catch (outerError) {
+  try {
+    pty = require('../build/Debug/pty.node');
+  } catch (innerError) {
+    console.error('innerError', innerError);
+    // Re-throw the exception from the Release require if the Debug require fails as well
+    throw outerError;
+  }
 }
 
 const DEFAULT_FILE = 'sh';
diff --git a/src/windowsPtyAgent.ts b/src/windowsPtyAgent.ts
index 141218062..cf8b65db6 100644
--- a/src/windowsPtyAgent.ts
+++ b/src/windowsPtyAgent.ts
@@ -61,16 +61,28 @@ export class WindowsPtyAgent {
       if (!conptyNative) {
         try {
           conptyNative = require('../build/Release/conpty.node');
-        } catch (err) {
-          conptyNative = require('../build/Debug/conpty.node');
+        } catch (outerError) {
+          try {
+            conptyNative = require('../build/Debug/conpty.node');
+          } catch (innerError) {
+            console.error('innerError', innerError);
+            // Re-throw the exception from the Release require if the Debug require fails as well
+            throw outerError;
+          }
         }
       }
     } else {
       if (!winptyNative) {
         try {
           winptyNative = require('../build/Release/pty.node');
-        } catch (err) {
-          winptyNative = require('../build/Debug/pty.node');
+        } catch (outerError) {
+          try {
+            winptyNative = require('../build/Debug/pty.node');
+          } catch (innerError) {
+            console.error('innerError', innerError);
+            // Re-throw the exception from the Release require if the Debug require fails as well
+            throw outerError;
+          }
         }
       }
     }