diff --git a/glass/publish.gradle b/glass/publish.gradle
index 909d4a284e..f2e3da7161 100644
--- a/glass/publish.gradle
+++ b/glass/publish.gradle
@@ -130,6 +130,14 @@ model {
                             }
 
                             from(applicationPath)
+
+                            if (binary.targetPlatform.operatingSystem.isWindows()) {
+                                def exePath = binary.executable.file.absolutePath
+                                exePath = exePath.substring(0, exePath.length() - 4)
+                                def pdbPath = new File(exePath + '.pdb')
+                                from(pdbPath)
+                            }
+
                             into(nativeUtils.getPlatformPath(binary))
                         }
 
diff --git a/outlineviewer/publish.gradle b/outlineviewer/publish.gradle
index b0fa202016..aa350098ba 100644
--- a/outlineviewer/publish.gradle
+++ b/outlineviewer/publish.gradle
@@ -76,6 +76,14 @@ model {
                             }
 
                             from(applicationPath)
+
+                            if (binary.targetPlatform.operatingSystem.isWindows()) {
+                                def exePath = binary.executable.file.absolutePath
+                                exePath = exePath.substring(0, exePath.length() - 4)
+                                def pdbPath = new File(exePath + '.pdb')
+                                from(pdbPath)
+                            }
+
                             into(nativeUtils.getPlatformPath(binary))
                         }
 
diff --git a/roborioteamnumbersetter/publish.gradle b/roborioteamnumbersetter/publish.gradle
index 103be9f5e6..3e8e6c3055 100644
--- a/roborioteamnumbersetter/publish.gradle
+++ b/roborioteamnumbersetter/publish.gradle
@@ -76,6 +76,14 @@ model {
                             }
 
                             from(applicationPath)
+
+                            if (binary.targetPlatform.operatingSystem.isWindows()) {
+                                def exePath = binary.executable.file.absolutePath
+                                exePath = exePath.substring(0, exePath.length() - 4)
+                                def pdbPath = new File(exePath + '.pdb')
+                                from(pdbPath)
+                            }
+
                             into(nativeUtils.getPlatformPath(binary))
                         }