diff --git a/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.cpp b/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.cpp
index 2c77dd56..de89ab06 100644
--- a/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.cpp
+++ b/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.cpp
@@ -73,8 +73,8 @@ namespace DebugServer::Gdb::CommandPackets
             const auto& registerGroupDescriptor = registerGroupDescriptorOpt->get();
 
             debugSession.connection.writePacket(PartialResponsePacket{StringService::toHex(
-                peripheralDescriptor.name + " peripheral registers, in " + registerGroupDescriptor.name
-                    + " register group:\n\n"
+                "\"" + peripheralDescriptor.name + "\" peripheral registers, in \"" + registerGroupDescriptor.name
+                    + "\" register group:\n\n"
             )});
             this->handleRegisterGroupOutput(registerGroupDescriptor, debugSession);
             debugSession.connection.writePacket(ResponsePacket{StringService::toHex("\n")});
@@ -96,13 +96,13 @@ namespace DebugServer::Gdb::CommandPackets
         DebugSession& debugSession
     ) {
         debugSession.connection.writePacket(PartialResponsePacket{StringService::toHex(
-            "---------- " + StringService::applyTerminalColor(
+            "---------- \"" + StringService::applyTerminalColor(
                 peripheralDescriptor.name,
                 StringService::TerminalColor::DARK_GREEN
-            ) + " (" + StringService::applyTerminalColor(
+            ) + "\" (`" + StringService::applyTerminalColor(
                 peripheralDescriptor.key,
                 StringService::TerminalColor::DARK_YELLOW
-            ) + ") peripheral registers ----------\n\n"
+            ) + "`) peripheral registers ----------\n\n"
         )});
 
         for (const auto& [groupKey, groupDescriptor] : peripheralDescriptor.registerGroupDescriptorsByKey) {
@@ -114,18 +114,18 @@ namespace DebugServer::Gdb::CommandPackets
         const Targets::TargetRegisterGroupDescriptor& groupDescriptor,
         DebugSession& debugSession
     ) {
-        for (const auto& [registerKey, registerDescriptor] : groupDescriptor.registerDescriptorsByKey) {
-            auto output = std::string{registerDescriptor.absoluteGroupKey + ", "};
-            output += registerDescriptor.key + ", ";
-            output += registerDescriptor.name + ", ";
+        for (const auto* registerDescriptor : this->sortRegisterDescriptors(groupDescriptor.registerDescriptorsByKey)) {
+            auto output = std::string{"`" + registerDescriptor->absoluteGroupKey + "`, "};
+            output += "`" + registerDescriptor->key + "`, ";
+            output += "\"" + registerDescriptor->name + "\", ";
             output += StringService::applyTerminalColor(
-                "0x" + StringService::asciiToUpper(StringService::toHex(registerDescriptor.startAddress)),
+                "0x" + StringService::asciiToUpper(StringService::toHex(registerDescriptor->startAddress)),
                 StringService::TerminalColor::BLUE
             ) + ", ";
-            output += std::to_string(registerDescriptor.size * 8) + "-bit";
+            output += std::to_string(registerDescriptor->size * 8) + "-bit";
 
-            if (registerDescriptor.description.has_value()) {
-                output += ", \"" + *(registerDescriptor.description) + "\"";
+            if (registerDescriptor->description.has_value()) {
+                output += ", \"" + *(registerDescriptor->description) + "\"";
             }
 
             output += "\n";
@@ -136,4 +136,31 @@ namespace DebugServer::Gdb::CommandPackets
             this->handleRegisterGroupOutput(subGroupDescriptor, debugSession);
         }
     }
+
+    std::vector<const Targets::TargetRegisterDescriptor*> ListRegistersMonitor::sortRegisterDescriptors(
+        const std::map<std::string, Targets::TargetRegisterDescriptor, std::less<void>>& map
+    ) {
+        auto output = std::vector<const Targets::TargetRegisterDescriptor*>{};
+        std::transform(
+            map.begin(),
+            map.end(),
+            std::back_inserter(output),
+            [] (const auto& pair) {
+                return &pair.second;
+            }
+        );
+
+        std::sort(
+            output.begin(),
+            output.end(),
+            [] (
+                const Targets::TargetRegisterDescriptor* descriptorA,
+                const Targets::TargetRegisterDescriptor* descriptorB
+            ) {
+                return descriptorA->startAddress < descriptorB->startAddress;
+            }
+        );
+
+        return output;
+    }
 }
diff --git a/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.hpp b/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.hpp
index 8705d3ab..c55b5a18 100644
--- a/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.hpp
+++ b/src/DebugServer/Gdb/CommandPackets/ListRegistersMonitor.hpp
@@ -1,6 +1,9 @@
 #pragma once
 
 #include <cstdint>
+#include <vector>
+#include <map>
+#include <string>
 
 #include "Monitor.hpp"
 
@@ -32,5 +35,9 @@ namespace DebugServer::Gdb::CommandPackets
             const Targets::TargetRegisterGroupDescriptor& groupDescriptor,
             DebugSession& debugSession
         );
+
+        static std::vector<const Targets::TargetRegisterDescriptor*> sortRegisterDescriptors(
+            const std::map<std::string, Targets::TargetRegisterDescriptor, std::less<void>>& map
+        );
     };
 }
diff --git a/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.cpp b/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.cpp
index ff5ca429..619b09c4 100644
--- a/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.cpp
+++ b/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.cpp
@@ -1,6 +1,7 @@
 #include "ReadRegistersMonitor.hpp"
 
 #include <bitset>
+#include <algorithm>
 
 #include "src/DebugServer/Gdb/ResponsePackets/ErrorResponsePacket.hpp"
 #include "src/DebugServer/Gdb/ResponsePackets/PartialResponsePacket.hpp"
@@ -77,8 +78,8 @@ namespace DebugServer::Gdb::CommandPackets
 
             if (!registerKey.has_value()) {
                 debugSession.connection.writePacket(PartialResponsePacket{StringService::toHex(
-                    "Reading all registers in " + registerGroupDescriptor.name + " register group, from "
-                        + peripheralDescriptor.name + " peripheral...\n\n"
+                    "Reading all registers in \"" + registerGroupDescriptor.name + "\" register group, from \""
+                        + peripheralDescriptor.name + "\" peripheral...\n\n"
                 )});
                 this->handleRegisterGroupOutput(registerGroupDescriptor, debugSession, targetControllerService);
                 debugSession.connection.writePacket(ResponsePacket{StringService::toHex("\n")});
@@ -110,7 +111,7 @@ namespace DebugServer::Gdb::CommandPackets
         DebugSession& debugSession,
         TargetControllerService& targetControllerService
     ) {
-        auto output = std::string{"\nName: " + registerDescriptor.name + "\n"};
+        auto output = std::string{"\nName: \"" + registerDescriptor.name + "\"\n"};
         output += "Address: " + StringService::applyTerminalColor(
             "0x" + StringService::asciiToUpper(StringService::toHex(registerDescriptor.startAddress)),
             StringService::TerminalColor::BLUE
@@ -137,9 +138,9 @@ namespace DebugServer::Gdb::CommandPackets
                 StringService::TerminalColor::DARK_YELLOW
             ) + ")\n";
 
-            for (const auto& [bitFieldKey, bitFieldDescriptor] : registerDescriptor.bitFieldDescriptorsByKey) {
-                output += bitFieldDescriptor.name + ": " + StringService::applyTerminalColor(
-                    "0b" + StringService::toBinaryStringWithMask(value, bitFieldDescriptor.mask),
+            for (const auto* bitFieldDescriptor : this->sortBitFieldDescriptors(registerDescriptor.bitFieldDescriptorsByKey)) {
+                output += bitFieldDescriptor->name + ": " + StringService::applyTerminalColor(
+                    "0b" + StringService::toBinaryStringWithMask(value, bitFieldDescriptor->mask),
                     StringService::TerminalColor::DARK_YELLOW
                 ) + " ";
 
@@ -160,7 +161,7 @@ namespace DebugServer::Gdb::CommandPackets
         TargetControllerService& targetControllerService
     ) {
         debugSession.connection.writePacket(PartialResponsePacket{StringService::toHex(
-            "Reading " + peripheralDescriptor.name + " peripheral registers...\n\n"
+            "Reading \"" + peripheralDescriptor.name + "\" peripheral registers...\n\n"
         )});
 
         for (const auto& [groupKey, groupDescriptor] : peripheralDescriptor.registerGroupDescriptorsByKey) {
@@ -175,23 +176,23 @@ namespace DebugServer::Gdb::CommandPackets
         DebugSession& debugSession,
         TargetControllerService& targetControllerService
     ) {
-        for (const auto& [registerKey, registerDescriptor] : groupDescriptor.registerDescriptorsByKey) {
-            auto output = std::string{registerDescriptor.absoluteGroupKey + ", "};
-            output += registerDescriptor.key + ", ";
-            output += registerDescriptor.name + ", ";
+        for (const auto* registerDescriptor : this->sortRegisterDescriptors(groupDescriptor.registerDescriptorsByKey)) {
+            auto output = std::string{"`" + registerDescriptor->absoluteGroupKey + "`, "};
+            output += "`" + registerDescriptor->key + "`, ";
+            output += "\"" + registerDescriptor->name + "\", ";
             output += StringService::applyTerminalColor(
-                "0x" + StringService::asciiToUpper(StringService::toHex(registerDescriptor.startAddress)),
+                "0x" + StringService::asciiToUpper(StringService::toHex(registerDescriptor->startAddress)),
                 StringService::TerminalColor::BLUE
             ) + ", ";
-            output += std::to_string(registerDescriptor.size * 8) + "-bit | ";
+            output += std::to_string(registerDescriptor->size * 8) + "-bit | ";
 
-            if (registerDescriptor.access.readable) {
+            if (registerDescriptor->access.readable) {
                 const auto value = IntegerService::toUint64(
-                    targetControllerService.readRegister(registerDescriptor)
+                    targetControllerService.readRegister(*registerDescriptor)
                 );
 
                 output += StringService::applyTerminalColor(
-                    "0x" + StringService::asciiToUpper(StringService::toHex(value)).substr(16 - (registerDescriptor.size * 2)),
+                    "0x" + StringService::asciiToUpper(StringService::toHex(value)).substr(16 - (registerDescriptor->size * 2)),
                     StringService::TerminalColor::DARK_YELLOW
                 );
                 output += " (" + StringService::applyTerminalColor(
@@ -199,13 +200,13 @@ namespace DebugServer::Gdb::CommandPackets
                     StringService::TerminalColor::DARK_YELLOW
                 );
                 output += ", " + StringService::applyTerminalColor(
-                    "0b" + std::bitset<64>{value}.to_string().substr(64 - (registerDescriptor.size * 8)),
+                    "0b" + std::bitset<64>{value}.to_string().substr(64 - (registerDescriptor->size * 8)),
                     StringService::TerminalColor::DARK_YELLOW
                 ) + ")";
 
-                for (const auto& [bitFieldKey, bitFieldDescriptor] : registerDescriptor.bitFieldDescriptorsByKey) {
-                    output += ", " + bitFieldDescriptor.name + ": " + StringService::applyTerminalColor(
-                        "0b" + StringService::toBinaryStringWithMask(value, bitFieldDescriptor.mask),
+                for (const auto* bitFieldDescriptor : this->sortBitFieldDescriptors(registerDescriptor->bitFieldDescriptorsByKey)) {
+                    output += ", " + bitFieldDescriptor->name + ": " + StringService::applyTerminalColor(
+                        "0b" + StringService::toBinaryStringWithMask(value, bitFieldDescriptor->mask),
                         StringService::TerminalColor::DARK_YELLOW
                     );
                 }
@@ -222,4 +223,58 @@ namespace DebugServer::Gdb::CommandPackets
             this->handleRegisterGroupOutput(subGroupDescriptor, debugSession, targetControllerService);
         }
     }
+
+    std::vector<const Targets::TargetRegisterDescriptor*> ReadRegistersMonitor::sortRegisterDescriptors(
+        const std::map<std::string, Targets::TargetRegisterDescriptor, std::less<void>>& map
+    ) {
+        auto output = std::vector<const Targets::TargetRegisterDescriptor*>{};
+        std::transform(
+            map.begin(),
+            map.end(),
+            std::back_inserter(output),
+            [] (const auto& pair) {
+                return &pair.second;
+            }
+        );
+
+        std::sort(
+            output.begin(),
+            output.end(),
+            [] (
+                const Targets::TargetRegisterDescriptor* descriptorA,
+                const Targets::TargetRegisterDescriptor* descriptorB
+            ) {
+                return descriptorA->startAddress < descriptorB->startAddress;
+            }
+        );
+
+        return output;
+    }
+
+    std::vector<const Targets::TargetBitFieldDescriptor*> ReadRegistersMonitor::sortBitFieldDescriptors(
+        const std::map<std::string, Targets::TargetBitFieldDescriptor>& map
+    ) {
+        auto output = std::vector<const Targets::TargetBitFieldDescriptor*>{};
+        std::transform(
+            map.begin(),
+            map.end(),
+            std::back_inserter(output),
+            [] (const auto& pair) {
+                return &pair.second;
+            }
+        );
+
+        std::sort(
+            output.begin(),
+            output.end(),
+            [] (
+                const Targets::TargetBitFieldDescriptor* descriptorA,
+                const Targets::TargetBitFieldDescriptor* descriptorB
+            ) {
+                return descriptorA->mask < descriptorB->mask;
+            }
+        );
+
+        return output;
+    }
 }
diff --git a/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.hpp b/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.hpp
index e179c9b4..fbce62ce 100644
--- a/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.hpp
+++ b/src/DebugServer/Gdb/CommandPackets/ReadRegistersMonitor.hpp
@@ -1,12 +1,16 @@
 #pragma once
 
 #include <cstdint>
+#include <vector>
+#include <map>
+#include <string>
 
 #include "Monitor.hpp"
 
-#include "src/Targets/TargetRegisterDescriptor.hpp"
-#include "src/Targets/TargetRegisterGroupDescriptor.hpp"
 #include "src/Targets/TargetPeripheralDescriptor.hpp"
+#include "src/Targets/TargetRegisterGroupDescriptor.hpp"
+#include "src/Targets/TargetRegisterDescriptor.hpp"
+#include "src/Targets/TargetBitFieldDescriptor.hpp"
 
 namespace DebugServer::Gdb::CommandPackets
 {
@@ -40,5 +44,13 @@ namespace DebugServer::Gdb::CommandPackets
             DebugSession& debugSession,
             Services::TargetControllerService& targetControllerService
         );
+
+        static std::vector<const Targets::TargetRegisterDescriptor*> sortRegisterDescriptors(
+            const std::map<std::string, Targets::TargetRegisterDescriptor, std::less<void>>& map
+        );
+
+        static std::vector<const Targets::TargetBitFieldDescriptor*> sortBitFieldDescriptors(
+            const std::map<std::string, Targets::TargetBitFieldDescriptor>& map
+        );
     };
 }
diff --git a/src/DebugServer/Gdb/CommandPackets/WriteRegisterMonitor.cpp b/src/DebugServer/Gdb/CommandPackets/WriteRegisterMonitor.cpp
index ba451cbd..2057a791 100644
--- a/src/DebugServer/Gdb/CommandPackets/WriteRegisterMonitor.cpp
+++ b/src/DebugServer/Gdb/CommandPackets/WriteRegisterMonitor.cpp
@@ -88,7 +88,7 @@ namespace DebugServer::Gdb::CommandPackets
             const auto& registerDescriptor = registerDescriptorOpt->get();
 
             if (!registerDescriptor.access.writable) {
-                throw Exception{registerDescriptor.name + " register is not writeable"};
+                throw Exception{"\"" + registerDescriptor.name + "\" register is not writeable"};
             }
 
             if (registerDescriptor.size > 8) {
@@ -120,8 +120,8 @@ namespace DebugServer::Gdb::CommandPackets
                 "Writing value " + StringService::applyTerminalColor(
                     "0x" + StringService::toHex(value).substr(16 - (registerDescriptor.size * 2)),
                     StringService::TerminalColor::DARK_YELLOW
-                ) + " (" +  std::to_string(buffer.size() * 8) + "-bit"  + ") to " + registerDescriptor.name
-                + " register, at address " + StringService::applyTerminalColor(
+                ) + " (" +  std::to_string(buffer.size() * 8) + "-bit"  + ") to \"" + registerDescriptor.name
+                + "\" register, at address " + StringService::applyTerminalColor(
                     "0x" + StringService::toHex(registerDescriptor.startAddress),
                     StringService::TerminalColor::BLUE
                 ) + ", via `" + registerDescriptor.addressSpaceKey + "` address space...\n"