diff --git a/src/server/server.h b/src/server/server.h
index c9d4698af8..ea1e94ec5f 100644
--- a/src/server/server.h
+++ b/src/server/server.h
@@ -118,5 +118,6 @@ COMMAND_HELPER(server_port_command, unsigned short *out);
 
 #define ERROR_SERVER_REMOTE_CLOSED		(-400)
 #define ERROR_CONNECTION_REJECTED		(-401)
+#define ERROR_SERVER_INTERRUPTED		(-402)
 
 #endif /* OPENOCD_SERVER_SERVER_H */
diff --git a/src/target/image.c b/src/target/image.c
index 9175c200af..440fe17d18 100644
--- a/src/target/image.c
+++ b/src/target/image.c
@@ -24,6 +24,7 @@
 #include "image.h"
 #include "target.h"
 #include <helper/log.h>
+#include <server/server.h>
 
 /* convert ELF header field to host endianness */
 #define field16(elf, field) \
@@ -1295,6 +1296,8 @@ int image_calculate_checksum(const uint8_t *buffer, uint32_t nbytes, uint32_t *c
 			crc = (crc << 8) ^ crc32_table[((crc >> 24) ^ *buffer++) & 255];
 		}
 		keep_alive();
+		if (openocd_is_shutdown_pending())
+			return ERROR_SERVER_INTERRUPTED;
 	}
 
 	LOG_DEBUG("Calculating checksum done; checksum=0x%" PRIx32, crc);
diff --git a/src/target/riscv/batch.c b/src/target/riscv/batch.c
index 290ce371be..7abe8ade3f 100644
--- a/src/target/riscv/batch.c
+++ b/src/target/riscv/batch.c
@@ -111,6 +111,9 @@ int riscv_batch_run(struct riscv_batch *batch)
 
 	keep_alive();
 
+	if (openocd_is_shutdown_pending())
+		return ERROR_SERVER_INTERRUPTED;
+
 	if (bscan_tunnel_ir_width != 0) {
 		/* need to right-shift "in" by one bit, because of clock skew between BSCAN TAP and DM TAP */
 		for (size_t i = 0; i < batch->used_scans; ++i) {
diff --git a/src/target/riscv/program.c b/src/target/riscv/program.c
index 22962fab4e..4543495192 100644
--- a/src/target/riscv/program.c
+++ b/src/target/riscv/program.c
@@ -47,6 +47,9 @@ int riscv_program_exec(struct riscv_program *p, struct target *t)
 {
 	keep_alive();
 
+	if (openocd_is_shutdown_pending())
+		return ERROR_SERVER_INTERRUPTED;
+
 	p->execution_result = RISCV_PROGBUF_EXEC_RESULT_UNKNOWN;
 	riscv_reg_t saved_registers[GDB_REGNO_XPR31 + 1];
 	for (size_t i = GDB_REGNO_ZERO + 1; i <= GDB_REGNO_XPR31; ++i) {
diff --git a/src/target/riscv/riscv-013.c b/src/target/riscv/riscv-013.c
index 2b8d381515..651342acd0 100644
--- a/src/target/riscv/riscv-013.c
+++ b/src/target/riscv/riscv-013.c
@@ -595,6 +595,9 @@ static int dmi_op_timeout(struct target *target, uint32_t *data_in,
 
 	keep_alive();
 
+	if (openocd_is_shutdown_pending())
+		return ERROR_SERVER_INTERRUPTED;
+
 	time_t start = time(NULL);
 	/* This first loop performs the request.  Note that if for some reason this
 	 * stays busy, it is actually due to the previous access. */
@@ -3241,6 +3244,9 @@ static int read_memory_bus_v1(struct target *target, target_addr_t address,
 						return ERROR_FAIL;
 					}
 					keep_alive();
+					if (openocd_is_shutdown_pending())
+						return ERROR_SERVER_INTERRUPTED;
+
 					dmi_status_t status = dmi_scan(target, NULL, &sbvalue[next_read_j],
 								       DMI_OP_READ, sbdata[j], 0, false);
 					/* By reading from sbdata0, we have just initiated another system bus read.
diff --git a/src/target/riscv/riscv.c b/src/target/riscv/riscv.c
index dd9ee43e8b..47674ad01b 100644
--- a/src/target/riscv/riscv.c
+++ b/src/target/riscv/riscv.c
@@ -5141,6 +5141,9 @@ static int riscv_set_or_write_register(struct target *target,
 
 	keep_alive();
 
+	if (openocd_is_shutdown_pending())
+		return ERROR_SERVER_INTERRUPTED;
+
 	if (regid == GDB_REGNO_PC) {
 		return riscv_set_or_write_register(target, GDB_REGNO_DPC, value, write_through);
 	} else if (regid == GDB_REGNO_PRIV) {
@@ -5238,6 +5241,9 @@ int riscv_get_register(struct target *target, riscv_reg_t *value,
 
 	keep_alive();
 
+	if (openocd_is_shutdown_pending())
+		return ERROR_SERVER_INTERRUPTED;
+
 	if (regid == GDB_REGNO_PC) {
 		return riscv_get_register(target, value, GDB_REGNO_DPC);
 	} else if (regid == GDB_REGNO_PRIV) {
diff --git a/src/target/target.c b/src/target/target.c
index 216dcb2eae..5e93c78734 100644
--- a/src/target/target.c
+++ b/src/target/target.c
@@ -1214,6 +1214,10 @@ int target_run_read_async_algorithm(struct target *target,
 		/* Avoid GDB timeouts */
 		keep_alive();
 
+		if (openocd_is_shutdown_pending()) {
+			retval = ERROR_SERVER_INTERRUPTED;
+			break;
+		}
 	}
 
 	if (retval != ERROR_OK) {
@@ -3225,8 +3229,11 @@ int target_wait_state(struct target *target, enum target_state state, unsigned i
 				nvp_value2name(nvp_target_state, state)->name);
 		}
 
-		if (cur-then > 500)
+		if (cur - then > 500) {
 			keep_alive();
+			if (openocd_is_shutdown_pending())
+				return ERROR_SERVER_INTERRUPTED;
+		}
 
 		if ((cur-then) > ms) {
 			LOG_ERROR("timed out while waiting for target %s",
@@ -3509,6 +3516,11 @@ static int target_fill_mem(struct target *target,
 			break;
 		/* avoid GDB timeouts */
 		keep_alive();
+
+		if (openocd_is_shutdown_pending()) {
+			retval = ERROR_SERVER_INTERRUPTED;
+			break;
+		}
 	}
 	free(target_buf);
 
@@ -3851,6 +3863,12 @@ static COMMAND_HELPER(handle_verify_image_command_internal, enum verify_mode ver
 							}
 						}
 						keep_alive();
+						if (openocd_is_shutdown_pending()) {
+							retval = ERROR_SERVER_INTERRUPTED;
+							free(data);
+							free(buffer);
+							goto done;
+						}
 					}
 				}
 				free(data);