diff --git a/src/commands/step_processor.go b/src/commands/step_processor.go
index 51724fde7..bd960cbee 100644
--- a/src/commands/step_processor.go
+++ b/src/commands/step_processor.go
@@ -1,9 +1,15 @@
 package commands
 
 import (
+	"fmt"
+	"io"
 	"net/http"
+	"os"
+	"strings"
 	"time"
 
+	"github.com/pkg/errors"
+
 	"github.com/go-openapi/swag"
 
 	log "github.com/sirupsen/logrus"
@@ -20,6 +26,14 @@ import (
 
 type HandlerType func(string, ...string) (stdout string, stderr string, exitCode int)
 
+type errorCode int
+
+// TODO - add an ErrorCode Enum to the swagger
+const (
+	Undetected        errorCode = 999
+	MediaDisconnected errorCode = 256
+)
+
 type stepSession struct {
 	session.InventorySession
 }
@@ -33,36 +47,30 @@ func newSession() *stepSession {
 	return &ret
 }
 
-func (s *stepSession) sendStepReply(stepType models.StepType, stepID, output, errStr string, exitCode int) {
-	if exitCode == 0 && alreadyExistsInService(stepType, output) {
-		s.Logger().Infof("Result for %s already exists in assisted service", string(stepType))
+func (s *stepSession) sendStepReply(reply models.StepReply) {
+	if reply.ExitCode == 0 && alreadyExistsInService(reply.StepType, reply.Output) {
+		s.Logger().Infof("Result for %s already exists in assisted service", string(reply.StepType))
 		return
 	}
 	logFunc := s.Logger().Infof
-	if exitCode != 0 {
+	if reply.ExitCode != 0 {
 		logFunc = s.Logger().Warnf
 	}
 
-	if stepType == models.StepTypeFreeNetworkAddresses {
+	if reply.StepType == models.StepTypeFreeNetworkAddresses {
 		// the free-addresses step's output spams the log too much
-		logFunc("Sending step <%s> reply error <%s> exit-code <%d>", stepID, errStr, exitCode)
+		logFunc("Sending step <%s> reply error <%s> exit-code <%d>", reply.StepID, reply.Error, reply.ExitCode)
 	} else {
-		logFunc("Sending step <%s> reply output <%s> error <%s> exit-code <%d>", stepID, output, errStr, exitCode)
+		logFunc("Sending step <%s> reply output <%s> error <%s> exit-code <%d>", reply.StepID, reply.Output, reply.Error, reply.ExitCode)
 	}
 
 	params := installer.PostStepReplyParams{
 		HostID:                strfmt.UUID(config.GlobalAgentConfig.HostID),
 		ClusterID:             strfmt.UUID(config.GlobalAgentConfig.ClusterID),
 		DiscoveryAgentVersion: &config.GlobalAgentConfig.AgentVersion,
+		Reply:                 &reply,
 	}
-	reply := models.StepReply{
-		StepType: stepType,
-		StepID:   stepID,
-		ExitCode: int64(exitCode),
-		Output:   output,
-		Error:    errStr,
-	}
-	params.Reply = &reply
+
 	_, err := s.Client().Installer.PostStepReply(s.Context(), &params)
 	if err != nil {
 		switch errValue := err.(type) {
@@ -75,12 +83,22 @@ func (s *stepSession) sendStepReply(stepType models.StepType, stepID, output, er
 		default:
 			s.Logger().WithError(err).Warn("Error posting step reply")
 		}
-	} else if exitCode == 0 {
-		storeInCache(stepType, output)
+	} else if reply.ExitCode == 0 {
+		storeInCache(reply.StepType, reply.Output)
 	}
 }
 
-func (s *stepSession) handleSingleStep(stepType models.StepType, stepID string, command string, args []string, handler HandlerType) {
+func (s *stepSession) createStepReply(stepType models.StepType, stepID string, output string, errStr string, exitCode int) models.StepReply {
+	return models.StepReply{
+		StepType: stepType,
+		StepID:   stepID,
+		ExitCode: int64(exitCode),
+		Output:   output,
+		Error:    errStr,
+	}
+}
+
+func (s *stepSession) handleSingleStep(stepType models.StepType, stepID string, command string, args []string, handler HandlerType) models.StepReply {
 	s.Logger().Infof("Executing step: <%s>, command: <%s>, args: <%v>", stepID, command, args)
 	stdout, stderr, exitCode := handler(command, args...)
 	if exitCode != 0 {
@@ -92,7 +110,8 @@ stderr:
 %v
 `, exitCode, stepID, command, args, stdout, stderr)
 	}
-	s.sendStepReply(stepType, stepID, stdout, stderr, exitCode)
+
+	return s.createStepReply(stepType, stepID, stdout, stderr, exitCode)
 }
 
 func (s *stepSession) handleSteps(steps *models.Steps) {
@@ -100,13 +119,98 @@ func (s *stepSession) handleSteps(steps *models.Steps) {
 		if step.Command == "" {
 			errStr := "Missing command"
 			s.Logger().Warn(errStr)
-			s.sendStepReply(step.StepType, step.StepID, "", errStr, -1)
+			s.sendStepReply(s.createStepReply(step.StepType, step.StepID, "", errStr, -1))
 			continue
 		}
-		go s.handleSingleStep(step.StepType, step.StepID, step.Command, step.Args, util.ExecutePrivileged)
+
+		go func(step *models.Step) {
+			if code, err := s.diagnoseSystem(); code != Undetected {
+				log.Errorf("System issue detected before running step: <%s>, command: <%s>, args: <%v>: %s - stopping the execution", step.StepID, step.Command, step.Args, err.Error())
+				s.sendStepReply(s.createStepReply(step.StepType, step.StepID, "", err.Error(), int(code)))
+				return
+			}
+
+			reply := s.handleSingleStep(step.StepType, step.StepID, step.Command, step.Args, util.ExecutePrivileged)
+
+			if reply.ExitCode != 0 {
+				if code, err := s.diagnoseSystem(); code != Undetected {
+					log.Errorf("System issue detected after running step: <%s>, command: <%s>, args: <%v>: %s", step.StepID, step.Command, step.Args, err.Error())
+					reply.ExitCode = int64(code)
+				}
+			}
+
+			s.sendStepReply(reply)
+		}(step)
 	}
 }
 
+// diagnoseSystem runs quick validations that need to need to occur before step and after a failure.
+// This is in order to detect and report known problems otherwise manifest as confusing error messages or stuck the whole system in the steps themselves.
+// One common example of that is virtual media disconnection.
+func (s *stepSession) diagnoseSystem() (errorCode, error) {
+	source, err := s.getMountpointSourceDeviceFile()
+
+	if err != nil {
+		log.Warn(err)
+		return Undetected, nil
+	}
+
+	if source == "" {
+		return Undetected, nil
+	}
+
+	file, err := os.Open(source)
+	if err != nil {
+		return MediaDisconnected, errors.Wrap(err, "cannot access the media (ISO) - media was likely disconnected")
+	}
+
+	defer file.Close()
+
+	_, err = io.ReadFull(file, make([]byte, 2, 2))
+	if err != nil {
+		return MediaDisconnected, errors.Wrap(err, "cannot read from the media (ISO) - media was likely disconnected")
+	}
+
+	return Undetected, nil
+}
+
+func (s *stepSession) getMountpointSourceDeviceFile() (string, error) {
+	mediaPath := "/run/media/iso"
+
+	// Media disconnection issue occurs only for a full-ISO installation
+	// mostly when serving iso via virtual media via sub optimal networking conditions.
+	// The minimal-ISO loaded very early and stay in memory. We don't need to read them from the ISO once they're loaded
+	// The media path exists only for the full-ISO so we can just eliminate this check.
+	if _, err := os.Stat(mediaPath); err != nil {
+		return "", nil
+	}
+
+	stdout, stderr, exitCode := util.ExecutePrivileged("findmnt", "--raw", "--noheadings", "--output", "SOURCE,TARGET", "--target", mediaPath)
+
+	errorMessage := "failed to validate media disconnection - continuing"
+
+	if exitCode != 0 {
+		return "", errors.Errorf("%s: %s", errorMessage, stderr)
+	}
+
+	if stdout == "" {
+		return "", errors.Errorf("%s: cannot find ISO mountpoint source", errorMessage)
+	}
+
+	fields := strings.Fields(stdout)
+
+	if fields[1] != mediaPath {
+		return "", fmt.Errorf("%s: media mounted to %s instead of directly to %s", errorMessage, fields[1], mediaPath)
+	}
+
+	source := fields[0]
+	if source == "" || !strings.HasPrefix(source, "/dev") {
+		return "", fmt.Errorf("%s: the mount source isn't a device file %s", errorMessage, source)
+	}
+
+	return source, nil
+}
+
 func (s *stepSession) processSingleSession() (int64, string) {
 	params := installer.GetNextStepsParams{
 		HostID:                strfmt.UUID(config.GlobalAgentConfig.HostID),