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If playing a character with a family sword or a particular set of armour that they wish to use throughout the game (from level 1 to level 20), can it start out unenchanted, then undergo a process to gain some kind of Magic Item property, and then much later, be re-enchanted with a more powerful Magic Item property?

I've read through the 'crafting magic items' section in the DMG but found nothing which mentions whether an existing item can be used for the process, nor whether the item in question can re-undergo the process to change its enchantment.

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This is a case where you need to work with your DM

As other answers point out: no specific rule on magical weapons, making or upgrading.

Just to make sure our terminology is aligned with the current edition, in 5e, Enchantment is a school of magic that is about influencing behavior. (Basic, p 80).

Enchantment spells affect the minds of others, influencing or controlling their behavior. Such spells can make enemies see the caster as a friend, force creatures to take a course of action, or even control another creature like a puppet.

In arriving at "how" you apply the guidance in the DMG (p. 128), a different school of magic looks like the basis for crafting or modifying magical things.

Transmutation.

"Transmutation spells change the properties of a creature, object, or environment."

Changing the properties of an object logically fits the school of magic background that leads to someone making an object magical, making one unmagical, or changing the nature of its magical features. (Again, how is very much up to the DM).

Supporting point in RAW:

In the PHB there is a class ability gained at sixth level for a Wizard specializing in the Transmutation school. He can can imbue a stone with magical properties. (Darkvision 60' being one; PHB, p. 119). While that particular magical object is limited to one per wizard, the Transmutation School of Magic fits into what older editions covered in "enchant an item" and other magical item creation schemes.

Chance of Failure

A chance of failure has been part of the "player character makes new magic item" since the original Spell Research rules in O D&D (p. 34, Men and Magic). This basic task a player could do, introducing new magic, and included a chance of failure. That system was gold based, and you could apply enough gold to get to 100% chance of success.

In 5e, the DM running the campaign has a more elegant tool: a DC assigned to any attempt to change the nature of the object. Having a chance of failure fits into D&D 5e's general theme of a reduced availability of magical items.

I could end up ruining Grandpa's sword if I try to make it a +2 blade

What a crafter could do to drive a DC toward a lower number depends on the DM's judgment and the suggestions / ingenuity of the player in coming up with risk mitigation strategies. Get assistance of a Transmutation specialist NPC? Find a scroll with a particular forumula for such an upgrade? (DM would need to provide this formula ...)


Historical note

The above approach, wherein one could try and either succeed or fail, is consistent with older editions. The AD&D 1e "Enchant an Item" spell had guidelines on purity of materials, time, cost, etcetera. And the attempt could still fail. The casting of a Permanency spell (8th level) spell was usually required to make the magic item work. (This spell typically cost a wizard the loss of a constitution point forever, so it was rare to find).

In the DMG of AD&D 1e (p. 116), the method indicates that magic users can make magic swords, but druids and clerics can only make items related to their class. A consistent theme in that rule set carried over from the OD&D; the provision that "it can go wrong." It has been said that 5e tries to restore some of the original feel. "It can go wrong" was part of that.

Real world analogy: you can put a lot of money into drilling a well for oil and still end up with a dry hole.

D & D's origin included published fiction in magical stories, speculative fiction, and swords and sorcery genres. Sources of this sort can help a DM flesh out / add depth to how his magic crafting requirements are built. A good example of fiction that illustrates how hard it is to make a magical item is a book by Avram Davidson called "The Phoenix and the Mirror."

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    \$\begingroup\$ This answer provides some useful historical details about how this was handled in earlier editions, but it also includes speculation, original ideas, and some off-topic discussion on the way "enchantment" as used in D&D 5e to mean something different to what it does in earlier editions and common parlance. Could it perhaps be pared down to the relevant points? \$\endgroup\$ – GMJoe Jun 12 '15 at 0:12
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    \$\begingroup\$ @gmjoe: Tightened up. I disagree about the distinction between enchantment and transmutation being off topic. The question asks about enchanting. In 5e, that school of magic has been directed towards a particular family of spells, which do not appear to include crafting. He also asked about risks of failure. \$\endgroup\$ – KorvinStarmast Jun 12 '15 at 13:10
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The DMG (p.128) says (my emphasis):

Magic items are the DM's purview, so you decide how they fall into the party's possession. As an option, you can allow player characters to craft magic items.

...

You can decide that certain items also require special materials or locations to be created.

So, can the item in question re-undergo the process to change its enchantment?

You decide

For other editions: 1st & 2nd adopted a similar stance to magic item creation (DM fiat), 3rd & 3.5 specifically allowed additional properties to be overlaid, I have no knowledge of 0 and 4th.

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There is no rule in the core rulebooks which allows for crafting a magic item out of a mundane item, nor any rules regarding enchantments. Therefore, any process your table uses to do this would have to be homebrewed, and the same for as any reversal process. That is, it's up to you how to reverse an enchantment, because (under 5e rules) there is no such thing as an enchantment.

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I've personally been DMing a game using 5e as an extremely loose guideline and in certain towns they have an enchanter who is able to place enchantments on a mundane item at a price + materials.

How good the enchantment is is decided by a d100 roll:

  • 1-5 fails and breaks the item and materials.

  • 6-25 fails and breaks the material but the item is intact.

  • 26-50 fails but the material and item are intact.

  • 51-75 is a lower enchantment being +1 to attack rolls.

  • 76- 95 is slightly better maybe adding an element to the damage.

  • 95-100 makes a pretty good enchantment which might add an additional d4 of elemental damage.

I pretty much have kept it pretty balanced for my group. I try not to make enchantments OP.

Aside from that I also have 1 player who is a Saladin using a cursed weapon with the option to banish the vengeful spirit from the blade making it basically a +1 longsword, or I have a side quest where he learns the history of the spirit trapped in the sword and can calm the vengeful spirit giving it a better property suited for his character. Then again as I said I am a DM who runs 5e very loosely homebrewing many aspects to make the game more enjoyable for my specific players who definitely prefer challenge over ease while playing.

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