diff --git a/src/Application.cpp b/src/Application.cpp
index 7af4761d..1f7c39fb 100644
--- a/src/Application.cpp
+++ b/src/Application.cpp
@@ -7,6 +7,7 @@
 
 #include "src/Logger/Logger.hpp"
 #include "src/Helpers/Paths.hpp"
+#include "src/Helpers/Process.hpp"
 
 #include "src/Exceptions/InvalidConfig.hpp"
 
@@ -509,7 +510,7 @@ namespace Bloom
     }
 
     void Application::onDebugSessionFinished(const Events::DebugSessionFinished& event) {
-        if (this->environmentConfig->shutdownPostDebugSession) {
+        if (this->environmentConfig->shutdownPostDebugSession || Process::isManagedByClion()) {
             this->shutdown();
         }
     }
diff --git a/src/DebugServer/Gdb/CommandPackets/Detach.cpp b/src/DebugServer/Gdb/CommandPackets/Detach.cpp
index 42feefdd..c8a4ed47 100644
--- a/src/DebugServer/Gdb/CommandPackets/Detach.cpp
+++ b/src/DebugServer/Gdb/CommandPackets/Detach.cpp
@@ -24,7 +24,7 @@ namespace Bloom::DebugServer::Gdb::CommandPackets
         Logger::debug("Handling Detach packet");
 
         try {
-            if (Process::isManagedByClion(Process::getParentProcessId())) {
+            if (Process::isManagedByClion()) {
                 targetControllerConsole.suspendTargetController();
             }
 
diff --git a/src/DebugServer/Gdb/GdbRspDebugServer.cpp b/src/DebugServer/Gdb/GdbRspDebugServer.cpp
index c50e4985..caa62934 100644
--- a/src/DebugServer/Gdb/GdbRspDebugServer.cpp
+++ b/src/DebugServer/Gdb/GdbRspDebugServer.cpp
@@ -125,7 +125,7 @@ namespace Bloom::DebugServer::Gdb
             std::bind(&GdbRspDebugServer::onTargetExecutionStopped, this, std::placeholders::_1)
         );
 
-        if (Process::isManagedByClion(Process::getParentProcessId())) {
+        if (Process::isManagedByClion()) {
             Logger::warning(
                 "Bloom's process is being managed by CLion - Bloom will automatically shutdown upon detaching from GDB."
             );
diff --git a/src/Helpers/Process.cpp b/src/Helpers/Process.cpp
index 6938e7da..0499760c 100644
--- a/src/Helpers/Process.cpp
+++ b/src/Helpers/Process.cpp
@@ -2,6 +2,7 @@
 
 #include <unistd.h>
 #include <string>
+#include <map>
 
 namespace Bloom
 {
@@ -13,47 +14,50 @@ namespace Bloom
         return getppid();
     }
 
-    bool Process::isManagedByClion(::pid_t processId) {
-        static auto cachedResult = std::optional<bool>();
+    bool Process::isManagedByClion(std::optional<::pid_t> parentProcessId) {
+        if (!parentProcessId.has_value()) {
+            parentProcessId = Process::getParentProcessId();
+        }
 
-        if (cachedResult.has_value()) {
-            return cachedResult.value();
+        static auto cachedResultsByProcessId = std::map<::pid_t, bool>();
+
+        if (cachedResultsByProcessId.contains(*parentProcessId)) {
+            return cachedResultsByProcessId.at(*parentProcessId);
         }
 
         // Walk the process tree until we find CLion
+        auto processId = *parentProcessId;
         while (processId != 0) {
             const auto processInfo = Process::getProcessInfo(processId);
 
-            if (!processInfo.has_value()) {
+            if (!processInfo) {
                 break;
             }
 
-            auto* processInfoPtr = processInfo.value();
-
-            const auto commandLine = std::string(processInfoPtr->cmd);
+            const auto commandLine = std::string(processInfo->cmd);
             if (commandLine.find("clion.sh") != std::string::npos) {
-                freeproc(processInfoPtr);
-                cachedResult = true;
+                cachedResultsByProcessId[*parentProcessId] = true;
                 return true;
             }
 
-            processId = processInfoPtr->ppid;
-            freeproc(processInfoPtr);
+            processId = processInfo->ppid;
         }
 
-        cachedResult = true;
+        cachedResultsByProcessId[*parentProcessId] = false;
         return false;
     }
 
-    std::optional<::proc_t*> Process::getProcessInfo(::pid_t processId) {
-        auto* proc = ::openproc(PROC_FILLSTAT | PROC_FILLARG | PROC_PID, &processId);
-        auto* processInfo = ::readproc(proc, NULL);
+    Process::ProcT Process::getProcessInfo(::pid_t processId) {
+        auto proc = std::unique_ptr<::PROCTAB, decltype(&::closeproc)>(
+            ::openproc(PROC_FILLSTAT | PROC_FILLARG | PROC_PID, &processId),
+            ::closeproc
+        );
+        auto processInfo = ProcT(::readproc(proc.get(), NULL), ::freeproc);
 
         if (processInfo == NULL) {
-            return std::nullopt;
+            return ProcT(nullptr, ::freeproc);
         }
 
-        closeproc(proc);
         return processInfo;
     }
 }
diff --git a/src/Helpers/Process.hpp b/src/Helpers/Process.hpp
index f49e7157..7e0be180 100644
--- a/src/Helpers/Process.hpp
+++ b/src/Helpers/Process.hpp
@@ -1,6 +1,7 @@
 #pragma once
 
 #include <optional>
+#include <memory>
 #include <proc/readproc.h>
 
 namespace Bloom
@@ -25,12 +26,16 @@ namespace Bloom
         /**
          * Returns true if the given process is managed by CLion.
          *
-         * @param processId
+         * @param parentProcessId
+         *  If not provided, this function will perform the check against the current process.
+         *
          * @return
          */
-        static bool isManagedByClion(::pid_t processId);
+        static bool isManagedByClion(std::optional<::pid_t> parentProcessId = std::nullopt);
+
 
     private:
-        static std::optional<::proc_t*> getProcessInfo(::pid_t processId);
+        using ProcT = std::unique_ptr<::proc_t, decltype(&::freeproc)>;
+        static ProcT getProcessInfo(::pid_t processId);
     };
 }