diff --git a/constructor/main.py b/constructor/main.py
index ee8104ad3..abf03ad2b 100644
--- a/constructor/main.py
+++ b/constructor/main.py
@@ -19,6 +19,7 @@
 import sys
 from os.path import abspath, expanduser, isdir, join
 from pathlib import Path
+from tempfile import TemporaryDirectory
 from textwrap import dedent
 
 from . import __version__
@@ -77,7 +78,22 @@ def get_output_filename(info):
     )
 
 
-def _win_install_needs_python_exe(conda_exe: str) -> bool:
+def _conda_exe_supports_logging(conda_exe: str, conda_exe_type: StandaloneExe | None) -> bool:
+    """Test if the standalone binary supports the the --log-file argument.
+
+    Only available for conda-standalone.
+    """
+    if not conda_exe_type:
+        return False
+    with TemporaryDirectory() as tmpdir:
+        logfile = Path(tmpdir, "conda.log")
+        subprocess.run([conda_exe, "--version", f"--log-file={logfile}"])
+        return logfile.exists()
+
+
+def _win_install_needs_python_exe(conda_exe: str, conda_exe_type: StandaloneExe | None) -> bool:
+    if not conda_exe_type:
+        return True
     results = subprocess.run(
         [conda_exe, "constructor", "windows", "--help"],
         capture_output=True,
@@ -270,6 +286,11 @@ def is_conda_meta_frozen(path_str: str) -> bool:
     else:
         info["_ignore_condarcs_arg"] = ""
 
+    info["_conda_exe_supports_logging"] = _conda_exe_supports_logging(
+        info["_conda_exe"],
+        info["_conda_exe_type"],
+    )
+
     if "pkg" in itypes:
         if (domains := info.get("pkg_domains")) is not None:
             domains = {key: str(val).lower() for key, val in domains.items()}
@@ -289,7 +310,10 @@ def is_conda_meta_frozen(path_str: str) -> bool:
             }
 
     if osname == "win":
-        info["_win_install_needs_python_exe"] = _win_install_needs_python_exe(info["_conda_exe"])
+        info["_win_install_needs_python_exe"] = _win_install_needs_python_exe(
+            info["_conda_exe"],
+            info["_conda_exe_type"],
+        )
 
     info["installer_type"] = itypes[0]
     fcp_main(info, verbose=verbose, dry_run=dry_run, conda_exe=conda_exe)
diff --git a/constructor/nsis/Utils.nsh b/constructor/nsis/Utils.nsh
index 986bf4344..d7ecd1ea0 100644
--- a/constructor/nsis/Utils.nsh
+++ b/constructor/nsis/Utils.nsh
@@ -1,128 +1,5 @@
 # Miscellaneous helpers.
 
-# We're not using RIndexOf at the moment, so ifdef it out for now (which
-# prevents the compiler warnings about an unused function).
-!ifdef INDEXOF
-Function IndexOf
-    Exch $R0
-    Exch
-    Exch $R1
-    Push $R2
-    Push $R3
-
-    StrCpy $R3 $R0
-    StrCpy $R0 -1
-    IntOp $R0 $R0 + 1
-
-    StrCpy $R2 $R3 1 $R0
-    StrCmp $R2 "" +2
-    StrCmp $R2 $R1 +2 -3
-
-    StrCpy $R0 -1
-
-    Pop $R3
-    Pop $R2
-    Pop $R1
-    Exch $R0
-FunctionEnd
-
-!macro IndexOf Var Str Char
-    Push "${Char}"
-    Push "${Str}"
-    Call IndexOf
-    Pop "${Var}"
-    !macroend
-!define IndexOf "!insertmacro IndexOf"
-
-Function RIndexOf
-    Exch $R0
-    Exch
-    Exch $R1
-    Push $R2
-    Push $R3
-
-    StrCpy $R3 $R0
-    StrCpy $R0 0
-    IntOp $R0 $R0 + 1
-    StrCpy $R2 $R3 1 -$R0
-    StrCmp $R2 "" +2
-    StrCmp $R2 $R1 +2 -3
-
-    StrCpy $R0 -1
-
-    Pop $R3
-    Pop $R2
-    Pop $R1
-    Exch $R0
-FunctionEnd
-
-!macro RIndexOf Var Str Char
-    Push "${Char}"
-    Push "${Str}"
-    Call RIndexOf
-    Pop "${Var}"
-!macroend
-
-!define RIndexOf "!insertmacro RIndexOf"
-!endif
-
-!macro StrStr
-    Exch $R1 ; st=haystack,old$R1, $R1=needle
-    Exch     ; st=old$R1,haystack
-    Exch $R2 ; st=old$R1,old$R2, $R2=haystack
-    Push $R3
-    Push $R4
-    Push $R5
-    StrLen $R3 $R1
-    StrCpy $R4 0
-    ; $R1=needle
-    ; $R2=haystack
-    ; $R3=len(needle)
-    ; $R4=cnt
-    ; $R5=tmp
-    loop:
-        StrCpy $R5 $R2 $R3 $R4
-        StrCmp $R5 $R1 done
-        StrCmp $R5 "" done
-        IntOp $R4 $R4 + 1
-        Goto loop
-     done:
-     StrCpy $R1 $R2 "" $R4
-     Pop $R5
-     Pop $R4
-     Pop $R3
-     Pop $R2
-     Exch $R1
-!macroend
-
-!macro GetShortPathName
-    Pop $0
-    # Return the 8.3 short path name for $0.  We ensure $0 exists by calling
-    # SetOutPath first (kernel32::GetShortPathName() fails otherwise).
-    SetOutPath $0
-    Push $0
-    Push ' '
-    Call StrStr
-    Pop $1
-    ${If} $1 != ""
-        # Our installation directory has a space, so use the short name from
-        # here in.  (This ensures no directories with spaces are written to
-        # registry values or configuration files.)  After GetShortPathName(),
-        # $0 will have the new name and $1 will have the length (if it's 0,
-        # assume an error occurred and leave $INSTDIR as it is).
-        System::Call "kernel32::GetShortPathName(\
-                        t'$RootDir', \
-                        t.R0, \
-                        i${NSIS_MAX_STRLEN}) i.R1"
-
-        ${If} $R1 > 0
-            Push $R0
-        ${EndIf}
-    ${Else}
-        Push $0
-    ${EndIf}
-!macroend
-
 ; Slightly modified version of http://nsis.sourceforge.net/IsWritable
 Function IsWritable
   !define IsWritable `!insertmacro IsWritableCall`
diff --git a/constructor/nsis/_nsis.py b/constructor/nsis/_nsis.py
index d83008854..383f3cd3e 100644
--- a/constructor/nsis/_nsis.py
+++ b/constructor/nsis/_nsis.py
@@ -35,24 +35,7 @@ def gui_excepthook(exctype, value, tb):
 
 sys.excepthook = gui_excepthook
 
-# If pythonw is being run, there may be no write function
-if sys.stdout and sys.stdout.write:
-    out = sys.stdout.write
-    err = sys.stderr.write
-else:
-    import ctypes
-    OutputDebugString = ctypes.windll.kernel32.OutputDebugStringW
-    OutputDebugString.argtypes = [ctypes.c_wchar_p]
-
-    def out(x):
-        OutputDebugString('_nsis.py: ' + x)
-
-    def err(x):
-        OutputDebugString('_nsis.py: Error: ' + x)
-
-
 allusers = (not exists(join(ROOT_PREFIX, '.nonadmin')))
-# out('allusers is %s\n' % allusers)
 
 # This must be the same as conda's binpath_from_arg() in conda/cli/activate.py
 PATH_SUFFIXES = ('',
@@ -96,7 +79,7 @@ def add_to_path(pyversion, arch):
     except IOError:
         old_prefixes = []
     for prefix in old_prefixes:
-        out('Removing old installation at %s from PATH (if any entries get found)\n' % (prefix))
+        print('Removing old installation at %s from PATH (if any entries get found)\n' % (prefix))
         remove_from_path(prefix)
 
     # add Anaconda to the path
diff --git a/constructor/nsis/_system_path.py b/constructor/nsis/_system_path.py
index ad391be86..ff35fe20e 100644
--- a/constructor/nsis/_system_path.py
+++ b/constructor/nsis/_system_path.py
@@ -11,28 +11,10 @@
 import ctypes
 import os
 import re
-import sys
 from ctypes import wintypes
 from os import path
 
-if sys.version_info[0] >= 3:
-    import winreg as reg
-else:
-    import _winreg as reg
-
-# If pythonw is being run, there may be no write function
-if sys.stdout and sys.stdout.write:
-    out = sys.stdout.write
-    err = sys.stderr.write
-else:
-    OutputDebugString = ctypes.windll.kernel32.OutputDebugStringW
-    OutputDebugString.argtypes = [ctypes.c_wchar_p]
-
-    def out(x):
-        OutputDebugString('_nsis.py: ' + x)
-
-    def err(x):
-        OutputDebugString('_nsis.py: Error: ' + x)
+import winreg as reg
 
 HWND_BROADCAST = 0xffff
 WM_SETTINGCHANGE = 0x001A
@@ -159,9 +141,6 @@ def add_to_system_path(paths, allusers=True, path_env_var='PATH'):
         final_value = final_value.replace('"', '')
         # Warn about directories that do not exist.
         directories = final_value.split(';')
-        for directory in directories:
-            if '%' not in directory and not os.path.exists(directory):
-                out("WARNING: Old PATH entry '%s' does not exist\n" % (directory))
         reg.SetValueEx(key, path_env_var, 0, reg_type, final_value)
 
     finally:
diff --git a/constructor/nsis/main.nsi.tmpl b/constructor/nsis/main.nsi.tmpl
index fb93badb6..8b25654c6 100644
--- a/constructor/nsis/main.nsi.tmpl
+++ b/constructor/nsis/main.nsi.tmpl
@@ -17,6 +17,16 @@ Unicode true
 !define LogSet "!insertmacro LogSetMacro"
 !macro LogSetMacro SETTING
   !ifdef ENABLE_LOGGING
+    ${If} ${SETTING} == "on"
+      ${IfNot} ${FileExists} "$INSTDIR\install.log"
+        # Enforce UTF-16 encoding in the log file
+        # NSIS doesn't write the correct BOM to log files,
+        # so each character will be followed by NUL.
+        FileOpen $R0 "$INSTDIR\install.log" w
+        FileWriteUTF16LE $R0 ""
+        FileClose $R0
+      ${EndIf}
+    ${EndIf}
     LogSet ${SETTING}
   !endif
 !macroend
@@ -31,9 +41,12 @@ Unicode true
 var /global QuietMode # "0" = print normally, "1" = do not print
 var /global StdOutHandle
 var /global StdOutHandleSet
-!define Print "!insertmacro PrintMacro"
-!macro PrintMacro INPUT_TEXT
-  DetailPrint "${INPUT_TEXT}"
+# Print and PrintToConsole are macros because it makes them easier to call.
+# However, that also means that registers must be handled with caution because
+# they will be overwritten in the macro. It is best to use $R* registers if
+# temporary variables need to be used.
+!define PrintToConsole "!insertmacro PrintToConsoleMacro"
+!macro PrintToConsoleMacro INPUT_TEXT
   ${If} ${Silent}
   ${AndIf} $QuietMode != "1"
     ${IfNot} $StdOutHandleSet == "1"
@@ -47,10 +60,24 @@ var /global StdOutHandleSet
         StrCpy $StdOutHandle $0
         StrCpy $StdOutHandleSet "1"
     ${EndIf}
-    FileWrite $StdOutHandle "${INPUT_TEXT}$\n"
+    # Only add newline if input text doesn't have it already
+    StrLen $2 "${INPUT_TEXT}"
+    IntOp $2 $2 - 1
+    StrCpy $2 "${INPUT_TEXT}" 1 $2
+    ${If} $2 == "$\n"
+      FileWrite $StdOutHandle "${INPUT_TEXT}"
+    ${Else}
+      FileWrite $StdOutHandle "${INPUT_TEXT}$\n"
+    ${EndIf}
   ${EndIf}
 !macroend
 
+!define Print "!insertmacro PrintMacro"
+!macro PrintMacro INPUT_TEXT
+  DetailPrint "${INPUT_TEXT}"
+  ${PrintToConsole} "${INPUT_TEXT}"
+!macroend
+
 !include "WinMessages.nsh"
 !include "WordFunc.nsh"
 !include "LogicLib.nsh"
@@ -98,8 +125,11 @@ ${Using:StrFunc} StrStr
 !define INIT_CONDA_DEFAULT_VALUE      {{ '1' if initialize_by_default else '0' }}
 !define PRODUCT_NAME                  "${NAME} ${VERSION} (${ARCH})"
 !define UNINSTALL_NAME                "{{ UNINSTALL_NAME }}"
-!define UNINSTREG                     "SOFTWARE\Microsoft\Windows\CurrentVersion\
-                                      \Uninstall\${UNINSTALL_NAME}"
+!define UNINSTREG                     "SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall\${UNINSTALL_NAME}"
+# Silent installations do not output to the console and outputs to stdout
+# are not written into install.log. STEP_LOG creates an intermittent file
+# that is output into these streams after the commands finish.
+!define STEP_LOG                      "$INSTDIR\.step.log"
 
 var /global INIT_CONDA
 var /global REG_PY
@@ -254,7 +284,6 @@ UninstPage Custom un.UninstCustomOptions_Show
 !insertmacro MUI_LANGUAGE "English"
 
 Function SkipPageIfUACInnerInstance
-    ${LogSet} on
     ${If} ${UAC_IsInnerInstance}
         Abort
     ${EndIf}
@@ -465,7 +494,6 @@ FunctionEnd
 !macroend
 
 Function InstModePage_RadioButton_OnClick
-    ${LogSet} on
     Exch $0
     Push $1
     Push $2
@@ -481,7 +509,6 @@ Function InstModePage_RadioButton_OnClick
 FunctionEnd
 
 Function InstModePage_Create
-    ${LogSet} on
     Push $0
     Push $1
     Push $2
@@ -528,7 +555,6 @@ Function InstModePage_Create
 FunctionEnd
 
 Function DisableBackButtonIfUACInnerInstance
-    ${LogSet} on
     Push $0
     ${If} ${UAC_IsInnerInstance}
         GetDlgItem $0 $HWNDParent 3
@@ -538,7 +564,6 @@ Function DisableBackButtonIfUACInnerInstance
 FunctionEnd
 
 Function RemoveNextBtnShield
-    ${LogSet} on
     Push $0
     GetDlgItem $0 $HWNDParent 1
     SendMessage $0 ${BCM_SETSHIELD} 0 0
@@ -546,7 +571,6 @@ Function RemoveNextBtnShield
 FunctionEnd
 
 Function InstModeChanged
-    ${LogSet} on
     # When using the installer with /S (silent mode), the /D option sets $INSTDIR,
     # and it is therefore important not to overwrite $INSTDIR here, but it is also
     # important that we do call SetShellVarContext with the appropriate value.
@@ -577,7 +601,6 @@ FunctionEnd
 !macroend
 
 Function InstModePage_Leave
-    ${LogSet} on
     Push $0
     Push $1
     Push $2
@@ -598,7 +621,6 @@ Function InstModePage_Leave
 FunctionEnd
 
 Function .onInit
-    ${LogSet} on
     Push $0
     Push $1
     Push $2
@@ -954,7 +976,6 @@ FunctionEnd
 
 # http://nsis.sourceforge.net/Check_for_spaces_in_a_directory_path
 Function CheckForSpaces
-    ${LogSet} on
     Exch $R0
     Push $R1
     Push $R2
@@ -978,7 +999,6 @@ FunctionEnd
 
 # http://nsis.sourceforge.net/StrCSpn,_StrCSpnReverse:_Scan_strings_for_characters
 Function StrCSpn
- ${LogSet} on
  Exch $R0 ; string to check
  Exch
  Exch $R1 ; string of chars
@@ -1038,7 +1058,6 @@ Pop $0
 
 
 Function OnDirectoryLeave
-    ${LogSet} on
     ${If} ${IsNonEmptyDirectory} "$InstDir"
         ${Print} "::error:: Directory '$INSTDIR' is not empty, please choose a different location."
         MessageBox MB_OK|MB_ICONEXCLAMATION \
@@ -1193,7 +1212,6 @@ Function OnDirectoryLeave
 FunctionEnd
 
 Function .onVerifyInstDir
-    ${LogSet} on
     StrLen $0 $Desktop
     StrCpy $0 $INSTDIR $0
     StrCmp $0 $Desktop 0 PathGood
@@ -1212,37 +1230,83 @@ Function un.OnDirectoryLeave
     confirmed_yes:
 FunctionEnd
 
-# Make function available for both installer and uninstaller
+# Make functions available for both installer and uninstaller
 # Uninstaller functions need an `un.` prefix, so we use a macro to do both
 # see https://nsis.sourceforge.io/Sharing_functions_between_Installer_and_Uninstaller
-!macro AbortRetryNSExecWaitMacro un
+!macro FunctionTemplates un
+    Function ${un}PrintFromStepLog
+        Exch $R0
+        Push $R1
+        Push $R2
+        ClearErrors
+        FileOpen $R1 "${STEP_LOG}" r
+        IfErrors close_file
+        read_line:
+            FileRead $R1 $R2
+            IfErrors close_file
+            ${If} $R0 == "ToConsole"
+            ${OrIf} $R0 == "both"
+                ${PrintToConsole} "$R2"
+            ${EndIf}
+            ${If} $R0 == "ToLog"
+            ${OrIf} $R0 == "both"
+                ${LogText} "$R2"
+            ${EndIf}
+            goto read_line
+        close_file:
+            FileClose $R1
+        Pop $R2
+        Pop $R1
+        Pop $R0
+    FunctionEnd
+
     Function ${un}AbortRetryNSExecWait
         # This function expects three arguments in the stack
-        # $1: 'WithLog' or 'NoLog': Use ExecToLog or just Exec, respectively
-        # $2: The message to show if an error occurred
-        # $3: The command to run, quoted
+        # $R1: 'WithLog' or 'NoLog': Use ExecToLog or just Exec, respectively
+        # $R2: The message to show if an error occurred
+        # $R3: The command to run, quoted
         # Note that the args need to be pushed to the stack in reverse order!
         # Search 'AbortRetryNSExecWait' in this script to see examples
-        ${LogSet} on
-        Pop $1
-        Pop $2
-        Pop $3
+        Pop $R1
+        Pop $R2
+        Pop $R3
         ${Do}
-            ${If} $1 == "WithLog"
-                nsExec::ExecToLog $3
-            ${ElseIf} $1 == "NoLog"
-                nsExec::Exec $3
+            # Execute command inside a subshell to catch issues with command execution.
+            # When binaries are executed with Exec or ExectToLog, only the output of these
+            # commands are logged. If they do not start successfully (e.g., if they don't exist),
+            # no error messages are returned. Using a subshell reveals these kinds of issues.
+            StrCpy $R3 '"$CMD_EXE" /D /C "$R3"'
+            ${If} $R1 == "WithLog"
+                nsExec::ExecToLog $R3
+            ${ElseIf} $R1 == "NoLog"
+                nsExec::Exec $R3
             ${Else}
-                ${Print} "::error:: AbortRetryNSExecWait: 1st argument must be 'WithLog' or 'NoLog'. You used: $1"
+                ${Print} "::error:: AbortRetryNSExecWait: 1st argument must be 'WithLog' or 'NoLog'. You used: $R1"
                 Abort
             ${EndIf}
-            pop $0
-            ${If} $0 != "0"
-                ${Print} "::error:: $2"
-                MessageBox MB_ABORTRETRYIGNORE|MB_ICONEXCLAMATION|MB_DEFBUTTON3 \
-                        $2 /SD IDIGNORE IDABORT abort IDRETRY retry
+            pop $R0
+            ${If} $R1 == "WithLog"
+            ${AndIf} ${FileExists} "${STEP_LOG}"
+                ${If} ${Silent}
+                    push "both"
+                    Call ${un}PrintFromStepLog
+                ${Else}
+                    push "ToLog"
+                    Call ${un}PrintFromStepLog
+                ${EndIf}
+            ${EndIf}
+            ${If} $R0 != "0"
+                # Always print on error
+                ${If} $R1 == "NoLog"
+                ${AndIf} ${FileExists} "${STEP_LOG}"
+                    Push "both"
+                    Call ${un}PrintFromStepLog
+                ${EndIf}
+                ${Print} "::error:: $R2"
+                MessageBox MB_ABORTRETRYIGNORE|MB_ICONEXCLAMATION|MB_DEFBUTTON1 \
+                        $R2 /SD IDABORT IDABORT abort IDRETRY retry
                 ; IDIGNORE: Continue anyway
-                StrCpy $0 "0"
+                StrCpy $R0 "0"
                 goto retry
             abort:
                 ; Abort installation
@@ -1250,11 +1314,14 @@ FunctionEnd
             retry:
                 ; Retry the nsExec command
             ${EndIf}
-        ${LoopWhile} $0 != "0"
+            ${If} ${FileExists} "${STEP_LOG}"
+                Delete "${STEP_LOG}"
+            ${EndIf}
+        ${LoopWhile} $R0 != "0"
     FunctionEnd
 !macroend
-!insertmacro AbortRetryNSExecWaitMacro ""
-!insertmacro AbortRetryNSExecWaitMacro "un."
+!insertmacro FunctionTemplates ""
+!insertmacro FunctionTemplates "un."
 
 {%- set pathname = "$INSTDIR\\condabin" if initialize_conda == "condabin" else "$INSTDIR\\Scripts & Library\\bin" %}
 !macro AddRemovePath add_remove un
@@ -1275,7 +1342,7 @@ FunctionEnd
         StrCpy $R1 "Failed to remove {{ NAME }} from PATH"
     ${EndIf}
     ${If} ${Silent}
-        push '"$INSTDIR\pythonw.exe" -E -s "$INSTDIR\Lib\_nsis.py" $R0'
+        push '"$INSTDIR\python.exe" -E -s "$INSTDIR\Lib\_nsis.py" $R0 > "${STEP_LOG}" 2>&1'
     ${Else}
         push '"$INSTDIR\python.exe" -E -s "$INSTDIR\Lib\_nsis.py" $R0'
     ${EndIf}
@@ -1293,7 +1360,7 @@ FunctionEnd
         StrCpy $R0 "remove"
         StrCpy $R1 'Failed to remove {{ NAME }} from PATH'
     ${EndIf}
-    push '"$INSTDIR\_conda.exe" constructor windows path --$R0=user --prefix "$INSTDIR" {{ pathflag }}'
+    push '"$INSTDIR\_conda.exe" constructor windows path --$R0=user --prefix "$INSTDIR" {{ pathflag }} {{ CONDA_LOG_ARG }}'
     push $R1
     push 'WithLog'
     call ${un}AbortRetryNSExecWait
@@ -1321,6 +1388,7 @@ FunctionEnd
               "Unable to determine the defaults permissions of the installation directory. "\
               "Ensure that you have read access to $INSTDIR and icacls.exe is in your PATH."
           ${Print} $R1
+          MessageBox MB_ICONSTOP $R1
           Abort
         ${EndIf}
         StrCpy $0 ""
@@ -1374,7 +1442,6 @@ FunctionEnd
 
 # Installer sections
 Section "Install"
-    ${LogSet} on
     ${If} ${Silent}
         call OnDirectoryLeave
     ${EndIf}
@@ -1382,6 +1449,7 @@ Section "Install"
     !insertmacro FindWindowsBinaries
 
     SetOutPath "$INSTDIR"
+    ${LogSet} on
 
     # Resolve INSTDIR so that paths and registry keys do not contain '..' or similar strings.
     # $0 is empty if the directory doesn't exist, but the File commands should have created it already.
@@ -1493,7 +1561,7 @@ Section "Install"
     System::Call 'kernel32::SetEnvironmentVariable(t,t)i("CONDA_SOLVER", "classic").r0'
     SetDetailsPrint TextOnly
     ${Print} "Checking virtual specs compatibility: {{ VIRTUAL_SPECS_DEBUG }}"
-    push '"$INSTDIR\_conda.exe" create --dry-run --prefix "$INSTDIR\envs\_virtual_specs_checks" --offline {{ VIRTUAL_SPECS }} {{ NO_RCS_ARG }}'
+    push '"$INSTDIR\_conda.exe" create --dry-run --prefix "$INSTDIR\envs\_virtual_specs_checks" --offline {{ VIRTUAL_SPECS }} {{ NO_RCS_ARG }} {{ CONDA_LOG_ARG }}'
     push 'Failed to check virtual specs: {{ VIRTUAL_SPECS_DEBUG }}'
     push 'WithLog'
     call AbortRetryNSExecWait
@@ -1505,19 +1573,22 @@ Section "Install"
     File {{ dist }}
 {%- endfor %}
 
-    SetDetailsPrint TextOnly
     ${Print} "Setting up the package cache..."
-    push '"$INSTDIR\_conda.exe" constructor --prefix "$INSTDIR" --extract-conda-pkgs'
+    push '"$INSTDIR\_conda.exe" constructor --prefix "$INSTDIR" --extract-conda-pkgs {{ CONDA_LOG_ARG }}'
     push 'Failed to extract packages'
-    push 'NoLog'
-    # We use NoLog here because TQDM progress bars are parsed as a single line in NSIS 3.08
-    # These can crash the installer if they get too long (a few packages is enough!)
+    push 'WithLog'
     call AbortRetryNSExecWait
-    SetDetailsPrint both
 
     IfFileExists "$INSTDIR\pkgs\pre_install.bat" 0 NoPreInstall
         ${Print} "Running pre_install scripts..."
-        push '"$CMD_EXE" /D /C "$INSTDIR\pkgs\pre_install.bat"'
+        # Output into step log if silent so that the output is visible in the console
+        # and the logs. For GUI installers, there is no good way to have live output
+        # and output into logs.
+        ${If} ${Silent}
+            push '"$INSTDIR\pkgs\pre_install.bat" > "${STEP_LOG}" 2>&1'
+        ${Else}
+            push '"$INSTDIR\pkgs\pre_install.bat"'
+        ${EndIf}
         push "Failed to run pre_install"
         push 'WithLog'
         call AbortRetryNSExecWait
@@ -1545,10 +1616,10 @@ Section "Install"
     # Run conda install
     ${If} $Ana_CreateShortcuts_State = ${BST_CHECKED}
         ${Print} "Installing packages for {{ env.name }}, creating shortcuts if necessary..."
-        push '"$INSTDIR\_conda.exe" install --offline -yp "{{ env.prefix }}" --file "{{ env.lockfile_txt }}" {{ env.shortcuts }} {{ env.no_rcs_arg }}'
+        push '"$INSTDIR\_conda.exe" install --offline -yp "{{ env.prefix }}" --file "{{ env.lockfile_txt }}" {{ env.shortcuts }} {{ env.no_rcs_arg }} {{ CONDA_LOG_ARG }}'
     ${Else}
         ${Print} "Installing packages for {{ env.name }}..."
-        push '"$INSTDIR\_conda.exe" install --offline -yp "{{ env.prefix }}" --file "{{ env.lockfile_txt }}" --no-shortcuts {{ env.no_rcs_arg }}'
+        push '"$INSTDIR\_conda.exe" install --offline -yp "{{ env.prefix }}" --file "{{ env.lockfile_txt }}" --no-shortcuts {{ env.no_rcs_arg }} {{ CONDA_LOG_ARG }}'
     ${EndIf}
     push 'Failed to link extracted packages to {{ env.prefix }}!'
     push 'WithLog'
@@ -1578,7 +1649,14 @@ Section "Install"
     ${If} ${FileExists} "$INSTDIR\pkgs\post_install.bat"
         ${If} $Ana_PostInstall_State = ${BST_CHECKED}
             ${Print} "Running post install..."
-            push '"$CMD_EXE" /D /C "$INSTDIR\pkgs\post_install.bat"'
+            # Output into step log if silent so that the output is visible in the console
+            # and the logs. For GUI installers, there is no good way to have live output
+            # and output into logs.
+            ${If} ${Silent}
+                push '"$INSTDIR\pkgs\post_install.bat" > "${STEP_LOG}" 2>&1"'
+            ${Else}
+                push '"$INSTDIR\pkgs\post_install.bat"'
+            ${EndIf}
             push "Failed to run post_install"
             push 'WithLog'
             call AbortRetryNSExecWait
@@ -1587,7 +1665,7 @@ Section "Install"
 
     ${If} $Ana_ClearPkgCache_State = ${BST_CHECKED}
         ${Print} "Clearing package cache..."
-        push '"$INSTDIR\_conda.exe" clean --all --force-pkgs-dirs --yes {{ NO_RCS_ARG }}'
+        push '"$INSTDIR\_conda.exe" clean --all --force-pkgs-dirs --yes {{ NO_RCS_ARG }} {{ CONDA_LOG_ARG }}'
         push 'Failed to clear package cache'
         push 'WithLog'
         call AbortRetryNSExecWait
@@ -1643,9 +1721,16 @@ Section "Install"
     # Enable inheritance on all files inside $INSTDIR.
     # Use icacls because it is much faster than custom NSIS solutions.
     # We continue on error because icacls fails on broken links.
-    push '"$ICACLS_EXE" "$INSTDIR\*" /inheritance:e /T /C /Q'
+    # Output into step log if silent so that the output is visible in the console
+    # and the logs. For GUI installers, there is no good way to have live output
+    # and output into logs.
+    ${If} ${Silent}
+        push '"$ICACLS_EXE" "$INSTDIR\*" /inheritance:e /T /C /Q > "${STEP_LOG}" 2>&1'
+    ${Else}
+        push '"$ICACLS_EXE" "$INSTDIR\*" /inheritance:e /T /C /Q'
+    ${EndIf}
     push 'Failed to enable inheritance for all files in the installation directory.'
-    push 'NoLog'
+    push 'WithLog'
     call AbortRetryNSExecWait
     ${Print} "Done!"
 SectionEnd
@@ -1674,6 +1759,9 @@ Section "Uninstall"
     # For long installation times, this may cause a buffer overflow, crashing the installer.
     System::Call 'kernel32::SetEnvironmentVariable(t,t)i("CONDA_QUIET", "1")".r0'
 
+    # Remove registry entries first because they are difficult to clean
+    # up manually if the uninstallation irrecoverably fails.
+
     # Read variables the uninstaller needs from the registry
     StrCpy $R0 "SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall"
     StrLen $R1 "Uninstall-${NAME}.exe"
@@ -1696,6 +1784,27 @@ Section "Uninstall"
         goto loop_path
     endloop_path:
 
+    ${If} $INSTALLER_NAME_FULL != ""
+        DeleteRegKey SHCTX "SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall\$INSTALLER_NAME_FULL"
+    ${EndIf}
+
+    # If Anaconda was registered as the official Python for this version,
+    # remove it from the registry
+    StrCpy $R0 "SOFTWARE\Python\PythonCore"
+    StrCpy $0 0
+    loop_py:
+        EnumRegKey $1 SHCTX $R0 $0
+        StrCmp $1 "" endloop_py
+        ReadRegStr $2 SHCTX "$R0\$1\InstallPath" ""
+        ${If} $2 == $INSTDIR
+            StrCpy $R1 $1
+            DeleteRegKey SHCTX "$R0\$1"
+            goto endloop_py
+        ${EndIf}
+        IntOp $0 $0 + 1
+        goto loop_py
+    endloop_py:
+
     # Extra info for pre_uninstall scripts
     System::Call 'kernel32::SetEnvironmentVariable(t,t)i("PREFIX", "$INSTDIR").r0'
     System::Call 'kernel32::SetEnvironmentVariable(t,t)i("INSTALLER_NAME", "${NAME}").r0'
@@ -1714,7 +1823,14 @@ Section "Uninstall"
 
     ${If} ${FileExists} "$INSTDIR\pkgs\pre_uninstall.bat"
         ${Print} "Running pre_uninstall scripts..."
-        push '"$CMD_EXE" /D /C "$INSTDIR\pkgs\pre_uninstall.bat"'
+        # Output into step log if silent so that the output is visible in the console
+        # and the logs. For GUI installers, there is no good way to have live output
+        # and output into logs.
+        ${If} ${Silent}
+            push '"$INSTDIR\pkgs\pre_uninstall.bat" > "${STEP_LOG}" 2>&1'
+        ${Else}
+            push '"$INSTDIR\pkgs\pre_uninstall.bat"'
+        ${EndIf}
         push "Failed to run pre_uninstall"
         push 'WithLog'
         call un.AbortRetryNSExecWait
@@ -1746,7 +1862,7 @@ Section "Uninstall"
     ${EndIf}
 
     ${Print} "Removing files and folders..."
-    push '"$INSTDIR\_conda.exe" constructor uninstall $R0 --prefix "$INSTDIR"'
+    push '"$INSTDIR\_conda.exe" constructor uninstall $R0 --prefix "$INSTDIR" {{ CONDA_LOG_ARG }}'
     push 'Failed to remove files and folders. Please see the log for more information.'
     push 'WithLog'
     SetDetailsPrint listonly
@@ -1756,6 +1872,9 @@ Section "Uninstall"
     # The uninstallation may leave the install.log, the uninstaller,
     # and .conda_trash files behind, so remove those manually.
     ${If} ${FileExists} "$INSTDIR"
+        # Stop logging or the uninstaller will not remove the install.log file
+        # without requiring a reboot
+        LogSet Off
         RMDir /r /REBOOTOK "$INSTDIR"
     ${EndIf}
 {%- else %}
@@ -1764,7 +1883,7 @@ Section "Uninstall"
     SetDetailsPrint both
     ${Print} "Deleting ${NAME} menus in {{ env.name }}..."
     SetDetailsPrint listonly
-    push '"$INSTDIR\_conda.exe" constructor --prefix "$INSTDIR{{ subdir }}" --rm-menus'
+    push '"$INSTDIR\_conda.exe" constructor --prefix "$INSTDIR{{ subdir }}" --rm-menus {{ CONDA_LOG_ARG }}'
     push 'Failed to delete menus in {{ env.name }}'
     push 'WithLog'
     call un.AbortRetryNSExecWait
@@ -1776,11 +1895,11 @@ Section "Uninstall"
     ${Else}
         StrCpy $R0 "system"
     ${EndIf}
-    # When running conda.bat directly, there is a non-fatal error
-    # that DOSKEY (called by conda_hook.bat) is not a valid command.
-    # While the operation still succeeds, this error is confusing.
-    # Calling via cmd.exe fixes that.
-    push '"$CMD_EXE" /D /C "$INSTDIR\condabin\conda.bat" init cmd.exe --reverse --$R0'
+    ${If} ${Silent}
+        push '"$INSTDIR\condabin\conda.bat" init cmd.exe --reverse --$R0 > "${STEP_LOG}" 2>&1'
+    ${Else}
+        push '"$INSTDIR\condabin\conda.bat" init cmd.exe --reverse --$R0'
+    ${EndIf}
     push 'Failed to clean AutoRun'
     push 'WithLog'
     call un.AbortRetryNSExecWait
@@ -1789,32 +1908,14 @@ Section "Uninstall"
     ${Print} "Removing files and folders..."
     nsExec::Exec 'cmd.exe /D /C RMDIR /Q /S "$INSTDIR"'
 
+    # Stop logging or the uninstaller will not remove the install.log file
+    # without requiring a reboot
+    LogSet Off
     # In case the last command fails, run the slow method to remove leftover
     RMDir /r /REBOOTOK "$INSTDIR"
 
 {%- endif %}
 
-    ${If} $INSTALLER_NAME_FULL != ""
-        DeleteRegKey SHCTX "SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall\$INSTALLER_NAME_FULL"
-    ${EndIf}
-
-    # If Anaconda was registered as the official Python for this version,
-    # remove it from the registry
-    StrCpy $R0 "SOFTWARE\Python\PythonCore"
-    StrCpy $0 0
-    loop_py:
-        EnumRegKey $1 SHCTX $R0 $0
-        StrCmp $1 "" endloop_py
-        ReadRegStr $2 SHCTX "$R0\$1\InstallPath" ""
-        ${If} $2 == $INSTDIR
-            StrCpy $R1 $1
-            DeleteRegKey SHCTX "$R0\$1"
-            goto endloop_py
-        ${EndIf}
-        IntOp $0 $0 + 1
-        goto loop_py
-    endloop_py:
-
     ${Print} "Done!"
     ${If} ${Silent}
         # give it some time so users can read the last lines
diff --git a/constructor/winexe.py b/constructor/winexe.py
index d225182af..cd1cf05aa 100644
--- a/constructor/winexe.py
+++ b/constructor/winexe.py
@@ -261,6 +261,9 @@ def make_nsi(
     approx_pkgs_size_kb = approx_size_kb(info, "pkgs")
 
     # UPPERCASE variables are unescaped (and unquoted)
+    variables["CONDA_LOG_ARG"] = (
+        '--log-file "${STEP_LOG}"' if info.get("_conda_exe_supports_logging") else ""
+    )
     variables["NAME"] = name
     variables["NSIS_DIR"] = NSIS_DIR
     variables["BITS"] = str(arch)
diff --git a/news/1108-improve-logging b/news/1108-improve-logging
new file mode 100644
index 000000000..265f2a1ce
--- /dev/null
+++ b/news/1108-improve-logging
@@ -0,0 +1,23 @@
+### Enhancements
+
+* Improve logging experience for EXE installers: (#1108)
+    - Use `cmd.exe` to run commands so that outputs are captured.
+    - Output command output in CLI installations.
+    - Prevent log builds from writing to log before installation directory exists.
+    - Remove registry entries while installation directory still exists so that errors are logged.
+
+### Bug fixes
+
+* <news item>
+
+### Deprecations
+
+* <news item>
+
+### Docs
+
+* <news item>
+
+### Other
+
+* <news item>
diff --git a/recipe/meta.yaml b/recipe/meta.yaml
index c5876d0cd..f9334ccb7 100644
--- a/recipe/meta.yaml
+++ b/recipe/meta.yaml
@@ -25,7 +25,7 @@ requirements:
     - conda >=4.6
     - python  # >=3.8
     - ruamel.yaml >=0.11.14,<0.19
-    - conda-standalone
+    - conda-standalone >=24.1.2
     - jinja2
     - jsonschema >=4
     - pillow >=3.1     # [win or osx]
diff --git a/tests/test_examples.py b/tests/test_examples.py
index a2ae8ad85..e335108bd 100644
--- a/tests/test_examples.py
+++ b/tests/test_examples.py
@@ -210,7 +210,7 @@ def _run_uninstaller_exe(
         f"_?={install_dir}",
     ]
     process = _execute(cmd, timeout=timeout, check=check)
-    if check:
+    if check and Path(install_dir, "install.log").exists():
         _check_installer_log(install_dir)
         remaining_files = list(install_dir.iterdir())
         if len(remaining_files) > 3: