diff --git a/src/DebugServer/Gdb/AvrGdb/AvrGdbRsp.cpp b/src/DebugServer/Gdb/AvrGdb/AvrGdbRsp.cpp
index 64df2aee..840bccea 100644
--- a/src/DebugServer/Gdb/AvrGdb/AvrGdbRsp.cpp
+++ b/src/DebugServer/Gdb/AvrGdb/AvrGdbRsp.cpp
@@ -176,7 +176,8 @@ namespace DebugServer::Gdb::AvrGdb
                  * The target stopped due to an intercepting breakpoint, but we're still within the stepping range,
                  * which can only mean that we weren't sure where this instruction would lead to.
                  *
-                 * We must perform a single step and see what happens.
+                 * We must perform a single step and see what happens. If the instruction takes us out of the stepping
+                 * range, we'll end the session and report back to GDB.
                  */
                 Logger::debug("Reached intercepting breakpoint within stepping range");
                 Logger::debug("Attempting single step from 0x" + StringService::toHex(programAddress));
@@ -191,7 +192,7 @@ namespace DebugServer::Gdb::AvrGdb
                  * We performed a single step once and we're still within the stepping range, so we're good to
                  * continue the range stepping session.
                  */
-                Logger::debug("Completed single step from an intercepted address - PC still within stepping range");
+                Logger::debug("Completed single step - PC still within stepping range");
                 Logger::debug("Continuing range stepping");
 
                 activeRangeSteppingSession->singleStepping = false;
diff --git a/src/DebugServer/Gdb/AvrGdb/CommandPackets/VContRangeStep.cpp b/src/DebugServer/Gdb/AvrGdb/CommandPackets/VContRangeStep.cpp
index b1ab4f72..4b6e80ae 100644
--- a/src/DebugServer/Gdb/AvrGdb/CommandPackets/VContRangeStep.cpp
+++ b/src/DebugServer/Gdb/AvrGdb/CommandPackets/VContRangeStep.cpp
@@ -205,7 +205,16 @@ namespace DebugServer::Gdb::AvrGdb::CommandPackets
             }
 
             debugSession.startRangeSteppingSession(std::move(rangeSteppingSession), targetControllerService);
-            targetControllerService.continueTargetExecution(std::nullopt, std::nullopt);
+
+            /*
+             * GDB expects us to start the range stepping session with a single step, and then only continue if the
+             * single step didn't immediately take us out of the stepping range.
+             *
+             * So we kick off a single step here, then let AvrGdbRsp::handleTargetStoppedGdbResponse() determine if
+             * we should continue. See that member function for more.
+             */
+            debugSession.activeRangeSteppingSession->singleStepping = true;
+            targetControllerService.stepTargetExecution(std::nullopt);
             debugSession.waitingForBreak = true;
 
         } catch (const Exception& exception) {
diff --git a/src/DebugServer/Gdb/RangeSteppingSession.hpp b/src/DebugServer/Gdb/RangeSteppingSession.hpp
index ffbb2aa9..fdb136df 100644
--- a/src/DebugServer/Gdb/RangeSteppingSession.hpp
+++ b/src/DebugServer/Gdb/RangeSteppingSession.hpp
@@ -28,8 +28,8 @@ namespace DebugServer::Gdb
         std::set<Targets::TargetMemoryAddress> interceptedAddresses;
 
         /**
-         * Whether we're currently performing a single step, in this session, to observe the behaviour of a particular
-         * instruction.
+         * Whether we're currently performing a single step, in this session, to start the session or observe the
+         * behaviour of a particular instruction.
          *
          * See AvrGdbRsp::handleTargetStoppedGdbResponse() for more.
          */