Mit diesem ordentlichen Plan sollte heute wirklich alles in Ordnung bleiben.

Breakdown of Mit diesem ordentlichen Plan sollte heute wirklich alles in Ordnung bleiben.

mit
with
heute
today
bleiben
to stay
der Plan
the plan
wirklich
really
sollen
should
alles
everything
ordentlich
tidy
in Ordnung
in order
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Questions & Answers about Mit diesem ordentlichen Plan sollte heute wirklich alles in Ordnung bleiben.

Why is Mit diesem ordentlichen Plan in the dative case, and why does ordentlichen end in -en?
The preposition mit always takes the dative case in German, so diesem Plan is dative masculine singular. After a definite or demonstrative article like diesem, adjectives use the weak declension, which gives them an -en ending (hence ordentlichen).
What nuance does ordentlich add in this context, and how is it different from gut or durchdacht?
Here ordentlich means “well-organized,” “thorough,” or “properly arranged.” Saying ein ordentlicher Plan emphasizes that everything is in its place and nothing is sloppy. In contrast, gut just means “good” in quality, and durchdacht focuses more on something being “well thought-through” rather than neatly arranged.
What does the phrase in Ordnung bleiben mean idiomatically, and how literal is it?
Literally in Ordnung bleiben is “to stay in order,” but idiomatically it means “to remain all right,” “keep under control,” or “not go wrong.” You could translate it as “everything should stay under control” or “everything should stay fine.”
Why is bleiben at the end of the sentence?
In German main clauses the conjugated (finite) verb—here sollte—must be in the second position, and any infinitives (like bleiben) go to the very end. Because sollen is acting as a modal here, its infinitive complement bleiben sits at the clause-final spot.
What does sollte express in this sentence—is it the past tense of sollen or a Konjunktiv II form?
Although the preterite (simple past) of sollen is also sollte, in this context it’s best understood as Konjunktiv II (subjunctive) expressing expectation or what “should” happen. It’s similar to the English “should” rather than a statement about the past.
How does the word order work with sollte, heute, wirklich, and alles?

German follows a general adverbial order of Time – Manner/Degree – Place. Here:

  1. sollte (finite verb in 2nd position)
  2. heute (time adverb)
  3. wirklich (degree adverb, “really”)
  4. alles (subject)
  5. in Ordnung (predicate phrase)
  6. bleiben (infinitive at the end)

So the sequence sollte heute wirklich alles in Ordnung bleiben obeys both the V2 rule and the time-manner-place/degree ordering.