diff --git a/src/target/cortex_a.c b/src/target/cortex_a.c
index ee27e1b21..46362017a 100644
--- a/src/target/cortex_a.c
+++ b/src/target/cortex_a.c
@@ -1169,6 +1169,29 @@ static int cortex_a_set_dscr_bits(struct target *target,
 	return retval;
 }
 
+/*
+ * Single-step on ARMv7a/r is implemented through a HW breakpoint that hits
+ * every instruction at any address except the address of the current
+ * instruction.
+ * Such HW breakpoint is never hit in case of a single instruction that jumps
+ * on itself (infinite loop), or a WFI or a WFE. In this case, halt the CPU
+ * after a timeout.
+ * The jump on itself would be executed several times before the timeout forces
+ * the halt, but this is not an issue. In ARMv7a/r there are few "pathological"
+ * instructions, listed below, that jumps on itself and that can have side
+ * effects if executed more than once; but they are not considered as real use
+ * cases generated by a compiler.
+ * Some example:
+ * - 'pop {pc}' or multi register 'pop' including PC, when the new PC value is
+ *   the same value of current PC. The single step will not stop at the first
+ *   'pop' and will continue taking values from the stack, modifying SP at each
+ *   iteration.
+ * - 'rfeda', 'rfedb', 'rfeia', 'rfeib', when the new PC value is the same
+ *   value of current PC. The register provided to the instruction (usually SP)
+ *   will be incremented or decremented at each iteration.
+ *
+ * TODO: fix exit in case of error, cleaning HW breakpoints.
+ */
 static int cortex_a_step(struct target *target, bool current, target_addr_t address,
 	bool handle_breakpoints)
 {
@@ -1227,15 +1250,34 @@ static int cortex_a_step(struct target *target, bool current, target_addr_t addr
 	if (retval != ERROR_OK)
 		return retval;
 
-	int64_t then = timeval_ms();
+	// poll at least once before starting the timeout
+	retval = cortex_a_poll(target);
+	if (retval != ERROR_OK)
+		return retval;
+
+	int64_t then = timeval_ms() + 100;
 	while (target->state != TARGET_HALTED) {
+		if (timeval_ms() > then)
+			break;
+
 		retval = cortex_a_poll(target);
 		if (retval != ERROR_OK)
 			return retval;
-		if (target->state == TARGET_HALTED)
-			break;
-		if (timeval_ms() > then + 1000) {
-			LOG_ERROR("timeout waiting for target halt");
+	}
+
+	if (target->state != TARGET_HALTED) {
+		LOG_TARGET_DEBUG(target, "timeout waiting for target halt, try halt");
+
+		retval = cortex_a_halt(target);
+		if (retval != ERROR_OK)
+			return retval;
+
+		retval = cortex_a_poll(target);
+		if (retval != ERROR_OK)
+			return retval;
+
+		if (target->state != TARGET_HALTED) {
+			LOG_TARGET_ERROR(target, "timeout waiting for target halt");
 			return ERROR_FAIL;
 		}
 	}
@@ -1255,9 +1297,6 @@ static int cortex_a_step(struct target *target, bool current, target_addr_t addr
 	if (breakpoint)
 		cortex_a_set_breakpoint(target, breakpoint, 0);
 
-	if (target->state != TARGET_HALTED)
-		LOG_DEBUG("target stepped");
-
 	return ERROR_OK;
 }