diff --git a/gui/builtinContextMenus/__init__.py b/gui/builtinContextMenus/__init__.py
index fd343cc51b..787ff25dde 100644
--- a/gui/builtinContextMenus/__init__.py
+++ b/gui/builtinContextMenus/__init__.py
@@ -20,6 +20,7 @@
 from gui.builtinContextMenus import itemStats
 from gui.builtinContextMenus import itemMarketJump
 from gui.builtinContextMenus import fitSystemSecurity  # Not really an item info but want to keep it here
+from gui.builtinContextMenus import fitPilotSecurity  # Not really an item info but want to keep it here
 from gui.builtinContextMenus import shipJump
 # Generic item manipulations
 from gui.builtinContextMenus import itemRemove
diff --git a/gui/builtinContextMenus/fitPilotSecurity.py b/gui/builtinContextMenus/fitPilotSecurity.py
new file mode 100644
index 0000000000..87b5d310d0
--- /dev/null
+++ b/gui/builtinContextMenus/fitPilotSecurity.py
@@ -0,0 +1,157 @@
+import re
+
+import wx
+
+import gui.fitCommands as cmd
+import gui.mainFrame
+from gui.contextMenu import ContextMenuUnconditional
+from service.fit import Fit
+
+_t = wx.GetTranslation
+
+
+class FitPilotSecurityMenu(ContextMenuUnconditional):
+
+    def __init__(self):
+        self.mainFrame = gui.mainFrame.MainFrame.getInstance()
+
+    def display(self, callingWindow, srcContext):
+        if srcContext != "fittingShip":
+            return False
+
+        fitID = self.mainFrame.getActiveFit()
+        fit = Fit.getInstance().getFit(fitID)
+
+        if fit.ship.name not in ('Pacifier', 'Enforcer', 'Marshal', 'Sidewinder', 'Cobra', 'Python'):
+            return
+
+        return True
+
+    def getText(self, callingWindow, itmContext):
+        return _t("Pilot Security Status")
+
+    def addOption(self, menu, optionLabel, optionValue):
+        id = ContextMenuUnconditional.nextID()
+        self.optionIds[id] = optionValue
+        menuItem = wx.MenuItem(menu, id, optionLabel, kind=wx.ITEM_CHECK)
+        menu.Bind(wx.EVT_MENU, self.handleMode, menuItem)
+        return menuItem
+
+    def addOptionCustom(self, menu, optionLabel):
+        id = ContextMenuUnconditional.nextID()
+        menuItem = wx.MenuItem(menu, id, optionLabel, kind=wx.ITEM_CHECK)
+        menu.Bind(wx.EVT_MENU, self.handleModeCustom, menuItem)
+        return menuItem
+
+    def getSubMenu(self, callingWindow, context, rootMenu, i, pitem):
+        fitID = self.mainFrame.getActiveFit()
+        fit = Fit.getInstance().getFit(fitID)
+        msw = True if "wxMSW" in wx.PlatformInfo else False
+        self.optionIds = {}
+        sub = wx.Menu()
+        presets = (-10, -8, -6, -4, -2, 0, 1, 2, 3, 4, 5)
+        # Inherit
+        char_sec_status = round(fit.character.secStatus, 2)
+        menuItem = self.addOption(rootMenu if msw else sub, _t('Character') + f' ({char_sec_status})', None)
+        sub.Append(menuItem)
+        menuItem.Check(fit.pilotSecurity is None)
+        # Custom
+        label = _t('Custom')
+        is_checked = False
+        if fit.pilotSecurity is not None and fit.pilotSecurity not in presets:
+            sec_status = round(fit.getPilotSecurity(), 2)
+            label += f' ({sec_status})'
+            is_checked = True
+        menuItem = self.addOptionCustom(rootMenu if msw else sub, label)
+        sub.Append(menuItem)
+        menuItem.Check(is_checked)
+        sub.AppendSeparator()
+        # Predefined options
+        for sec_status in presets:
+            menuItem = self.addOption(rootMenu if msw else sub, str(sec_status), sec_status)
+            sub.Append(menuItem)
+            menuItem.Check(fit.pilotSecurity == sec_status)
+        return sub
+
+    def handleMode(self, event):
+        optionValue = self.optionIds[event.Id]
+        self.mainFrame.command.Submit(cmd.GuiChangeFitPilotSecurityCommand(
+                fitID=self.mainFrame.getActiveFit(),
+                secStatus=optionValue))
+
+    def handleModeCustom(self, event):
+        fitID = self.mainFrame.getActiveFit()
+        fit = Fit.getInstance().getFit(fitID)
+        sec_status = fit.getPilotSecurity()
+
+        with SecStatusChanger(self.mainFrame, value=sec_status) as dlg:
+            if dlg.ShowModal() == wx.ID_OK:
+                cleanInput = re.sub(r'[^0-9.\-+]', '', dlg.input.GetLineText(0).strip())
+                if cleanInput:
+                    try:
+                        cleanInputFloat = float(cleanInput)
+                    except ValueError:
+                        return
+                else:
+                    return
+                self.mainFrame.command.Submit(cmd.GuiChangeFitPilotSecurityCommand(
+                        fitID=fitID, secStatus=max(-10.0, min(5.0, cleanInputFloat))))
+
+
+FitPilotSecurityMenu.register()
+
+
+class SecStatusChanger(wx.Dialog):
+
+    def __init__(self, parent, value):
+        super().__init__(parent, title=_t('Change Security Status'), style=wx.DEFAULT_DIALOG_STYLE)
+        self.SetMinSize((346, 156))
+
+        bSizer1 = wx.BoxSizer(wx.VERTICAL)
+
+        bSizer2 = wx.BoxSizer(wx.VERTICAL)
+        text = wx.StaticText(self, wx.ID_ANY, _t('Security Status (min -10.0, max 5.0):'))
+        bSizer2.Add(text, 0)
+
+        bSizer1.Add(bSizer2, 0, wx.ALL, 10)
+
+        self.input = wx.TextCtrl(self, wx.ID_ANY, style=wx.TE_PROCESS_ENTER)
+        if value is None:
+            value = '0.0'
+        else:
+            if value == int(value):
+                value = int(value)
+            value = str(value)
+        self.input.SetValue(value)
+
+        bSizer1.Add(self.input, 0, wx.LEFT | wx.RIGHT | wx.EXPAND, 15)
+
+        bSizer3 = wx.BoxSizer(wx.VERTICAL)
+        bSizer3.Add(wx.StaticLine(self, wx.ID_ANY), 0, wx.BOTTOM | wx.EXPAND, 15)
+
+        bSizer3.Add(self.CreateStdDialogButtonSizer(wx.OK | wx.CANCEL), 0, wx.EXPAND)
+        bSizer1.Add(bSizer3, 0, wx.ALL | wx.EXPAND, 10)
+
+        self.input.Bind(wx.EVT_CHAR, self.onChar)
+        self.input.Bind(wx.EVT_TEXT_ENTER, self.processEnter)
+        self.SetSizer(bSizer1)
+        self.Fit()
+        self.CenterOnParent()
+        self.input.SetFocus()
+        self.input.SelectAll()
+
+    def processEnter(self, evt):
+        self.EndModal(wx.ID_OK)
+
+    # checks to make sure it's valid number
+    @staticmethod
+    def onChar(event):
+        key = event.GetKeyCode()
+
+        acceptable_characters = '1234567890.-+'
+        acceptable_keycode = [3, 22, 13, 8, 127]  # modifiers like delete, copy, paste
+        if key in acceptable_keycode or key >= 255 or (key < 255 and chr(key) in acceptable_characters):
+            event.Skip()
+            return
+        else:
+            return False
diff --git a/gui/fitCommands/__init__.py b/gui/fitCommands/__init__.py
index ab56b1ddcd..78536054a0 100644
--- a/gui/fitCommands/__init__.py
+++ b/gui/fitCommands/__init__.py
@@ -12,6 +12,7 @@
 from .gui.commandFit.add import GuiAddCommandFitsCommand
 from .gui.commandFit.remove import GuiRemoveCommandFitsCommand
 from .gui.commandFit.toggleStates import GuiToggleCommandFitStatesCommand
+from .gui.fitPilotSecurity import GuiChangeFitPilotSecurityCommand
 from .gui.fitRename import GuiRenameFitCommand
 from .gui.fitRestrictionToggle import GuiToggleFittingRestrictionsCommand
 from .gui.fitSystemSecurity import GuiChangeFitSystemSecurityCommand
diff --git a/gui/fitCommands/calc/fitPilotSecurity.py b/gui/fitCommands/calc/fitPilotSecurity.py
new file mode 100644
index 0000000000..8f09925085
--- /dev/null
+++ b/gui/fitCommands/calc/fitPilotSecurity.py
@@ -0,0 +1,32 @@
+import wx
+from logbook import Logger
+
+from service.fit import Fit
+
+
+pyfalog = Logger(__name__)
+
+
+class CalcChangeFitPilotSecurityCommand(wx.Command):
+
+    def __init__(self, fitID, secStatus):
+        wx.Command.__init__(self, True, 'Change Fit Pilot Security')
+        self.fitID = fitID
+        self.secStatus = secStatus
+        self.savedSecStatus = None
+
+    def Do(self):
+        pyfalog.debug('Doing changing pilot security status of fit {} to {}'.format(self.fitID, self.secStatus))
+        fit = Fit.getInstance().getFit(self.fitID, basic=True)
+        # Fetching status via getter and then saving 'raw' security status
+        # is intentional, to restore pre-change state properly
+        if fit.pilotSecurity == self.secStatus:
+            return False
+        self.savedSecStatus = fit.pilotSecurity
+        fit.pilotSecurity = self.secStatus
+        return True
+
+    def Undo(self):
+        pyfalog.debug('Undoing changing pilot security status of fit {} to {}'.format(self.fitID, self.secStatus))
+        cmd = CalcChangeFitPilotSecurityCommand(fitID=self.fitID, secStatus=self.savedSecStatus)
+        return cmd.Do()
diff --git a/gui/fitCommands/gui/fitPilotSecurity.py b/gui/fitCommands/gui/fitPilotSecurity.py
new file mode 100644
index 0000000000..2f6123c4a2
--- /dev/null
+++ b/gui/fitCommands/gui/fitPilotSecurity.py
@@ -0,0 +1,36 @@
+import wx
+from service.fit import Fit
+
+import eos.db
+import gui.mainFrame
+from gui import globalEvents as GE
+from gui.fitCommands.helpers import InternalCommandHistory
+from gui.fitCommands.calc.fitPilotSecurity import CalcChangeFitPilotSecurityCommand
+
+
+class GuiChangeFitPilotSecurityCommand(wx.Command):
+
+    def __init__(self, fitID, secStatus):
+        wx.Command.__init__(self, True, 'Change Fit Pilot Security')
+        self.internalHistory = InternalCommandHistory()
+        self.fitID = fitID
+        self.secStatus = secStatus
+
+    def Do(self):
+        cmd = CalcChangeFitPilotSecurityCommand(fitID=self.fitID, secStatus=self.secStatus)
+        success = self.internalHistory.submit(cmd)
+        eos.db.flush()
+        sFit = Fit.getInstance()
+        sFit.recalc(self.fitID)
+        eos.db.commit()
+        wx.PostEvent(gui.mainFrame.MainFrame.getInstance(), GE.FitChanged(fitIDs=(self.fitID,)))
+        return success
+
+    def Undo(self):
+        success = self.internalHistory.undoAll()
+        eos.db.flush()
+        sFit = Fit.getInstance()
+        sFit.recalc(self.fitID)
+        eos.db.commit()
+        wx.PostEvent(gui.mainFrame.MainFrame.getInstance(), GE.FitChanged(fitIDs=(self.fitID,)))
+        return success